@tiptap/markdown 3.20.6 → 3.21.0

package/dist/index.cjs

@@ -103,12 +103,12 @@ var MarkdownManager = class {
    * @param options.extensions An array of Tiptap extensions to register for markdown parsing and rendering.
    */
   constructor(options) {
+    this.activeParseLexer = null;
     this.baseExtensions = [];
     this.extensions = [];
     this.lastParseResult = null;
     var _a, _b, _c, _d, _e;
     this.markedInstance = (_a = options == null ? void 0 : options.marked) != null ? _a : _marked.marked;
-    this.lexer = new this.markedInstance.Lexer();
     this.indentStyle = (_c = (_b = options == null ? void 0 : options.indentation) == null ? void 0 : _b.style) != null ? _c : "space";
     this.indentSize = (_e = (_d = options == null ? void 0 : options.indentation) == null ? void 0 : _d.size) != null ? _e : 2;
     this.baseExtensions = (options == null ? void 0 : options.extensions) || [];
@@ -120,9 +120,8 @@ var MarkdownManager = class {
     if (options == null ? void 0 : options.extensions) {
       this.baseExtensions = options.extensions;
       const flattened = _core.flattenExtensions.call(void 0, options.extensions);
-      flattened.forEach((ext) => this.registerExtension(ext, false));
+      flattened.forEach((ext) => this.registerExtension(ext));
     }
-    this.lexer = new this.markedInstance.Lexer();
   }
   /** Returns the underlying marked instance. */
   get instance() {
@@ -145,7 +144,7 @@ var MarkdownManager = class {
    * `markdownName`, `parseMarkdown`, `renderMarkdown` and `priority` from the
    * extension config (using the same resolution used across the codebase).
    */
-  registerExtension(extension, recreateLexer = true) {
+  registerExtension(extension) {
     var _a, _b;
     this.extensions.push(extension);
     const name = extension.name;
@@ -177,11 +176,21 @@ var MarkdownManager = class {
     }
     if (tokenizer && this.hasMarked()) {
       this.registerTokenizer(tokenizer);
-      if (recreateLexer) {
-        this.lexer = new this.markedInstance.Lexer();
-      }
     }
   }
+  createLexer() {
+    return new this.markedInstance.Lexer();
+  }
+  createTokenizerHelpers(lexer) {
+    return {
+      inlineTokens: (src) => lexer.inlineTokens(src),
+      blockTokens: (src) => lexer.blockTokens(src)
+    };
+  }
+  tokenizeInline(src) {
+    var _a;
+    return ((_a = this.activeParseLexer) != null ? _a : this.createLexer()).inlineTokens(src);
+  }
   /**
    * Register a custom tokenizer with marked.js for parsing non-standard markdown syntax.
    */
@@ -190,20 +199,12 @@ var MarkdownManager = class {
       return;
     }
     const { name, start, level = "inline", tokenize } = tokenizer;
-    const tokenizeInline = (src) => {
-      return this.lexer.inlineTokens(src);
-    };
-    const tokenizeBlock = (src) => {
-      return this.lexer.blockTokens(src);
-    };
-    const helper = {
-      inlineTokens: tokenizeInline,
-      blockTokens: tokenizeBlock
-    };
+    const createTokenizerHelpers = this.createTokenizerHelpers.bind(this);
+    const createLexer = this.createLexer.bind(this);
     let startCb;
     if (!start) {
       startCb = (src) => {
-        const result = tokenize(src, [], helper);
+        const result = tokenize(src, [], this.createTokenizerHelpers(this.createLexer()));
         if (result && result.raw) {
           const index = src.indexOf(result.raw);
           return index;
@@ -217,7 +218,8 @@ var MarkdownManager = class {
       name,
       level,
       start: startCb,
-      tokenizer: (src, tokens) => {
+      tokenizer(src, tokens) {
+        const helper = this.lexer ? createTokenizerHelpers(this.lexer) : createTokenizerHelpers(createLexer());
         const result = tokenize(src, tokens, helper);
         if (result && result.type) {
           return {
@@ -290,12 +292,19 @@ var MarkdownManager = class {
     if (!this.hasMarked()) {
       throw new Error("No marked instance available for parsing");
     }
-    const tokens = this.markedInstance.lexer(markdown);
-    const content = this.parseTokens(tokens, true);
-    return {
-      type: "doc",
-      content
-    };
+    const previousParseLexer = this.activeParseLexer;
+    const parseLexer = this.createLexer();
+    this.activeParseLexer = parseLexer;
+    try {
+      const tokens = parseLexer.lex(markdown);
+      const content = this.parseTokens(tokens, true);
+      return {
+        type: "doc",
+        content
+      };
+    } finally {
+      this.activeParseLexer = previousParseLexer;
+    }
   }
   /**
    * Convert an array of marked tokens into Tiptap JSON nodes using registered extension handlers.
@@ -426,7 +435,7 @@ var MarkdownManager = class {
           indentLevel,
           checked: checked != null ? checked : false,
           text: mainContent,
-          tokens: this.lexer.inlineTokens(mainContent),
+          tokens: this.tokenizeInline(mainContent),
           nestedTokens
         };
       }

package/dist/index.cjs.map

@@ -1 +1 @@
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is provided as.\n     *\n     * @default 'json'\n     */\n    contentType?: ContentType\n  }\n\n  interface InsertContentAtOptions {\n    /**\n     * The content type the content is provided as.\n     *\n     * @default 'json'\n     */\n    contentType?: ContentType\n  }\n\n  interface SetContentOptions {\n    /**\n     * The content type the content is provided as.\n     *\n     * @default 'json'\n     */\n    contentType?: ContentType\n  }\n}\n\nexport type MarkdownExtensionOptions = {\n  /**\n   * Configure the indentation style and size for lists and code blocks.\n   * - `style`: Choose between spaces or tabs. Default is 'space'.\n   * - `size`: Number of spaces or tabs for indentation. Default is 2.\n   */\n  indentation?: { style?: 'space' | 'tab'; size?: number }\n\n  /**\n   * Use a custom version of `marked` for markdown parsing and serialization.\n   * If not provided, the default `marked` instance will be used.\n   */\n  marked?: typeof marked\n\n  /**\n   * Options to pass to `marked.setOptions()`.\n   * See the [marked documentation](https://marked.js.org/using_advanced#options) for available options.\n   */\n  markedOptions?: Parameters<typeof marked.setOptions>[0]\n}\n\nexport type MarkdownExtensionStorage = {\n  manager: MarkdownManager\n}\n\nexport const Markdown = Extension.create<MarkdownExtensionOptions, MarkdownExtensionStorage>({\n  name: 'markdown',\n\n  addOptions() {\n    return {\n      indentation: { style: 'space', size: 2 },\n      marked: undefined,\n      markedOptions: {},\n    }\n  },\n\n  addCommands() {\n    return {\n      setContent: (content, options?: MarkdownSetContentOptions) => {\n        // if no contentType is specified, we assume the content is in JSON format OR HTML format\n        if (!options?.contentType) {\n          return commands.setContent(content, options)\n        }\n\n        const actualContentType = assumeContentType(content, options?.contentType)\n\n        if (actualContentType !== 'markdown' || !this.editor.markdown) {\n          return commands.setContent(content, options)\n        }\n\n        const mdContent = this.editor.markdown.parse(content as string)\n        return commands.setContent(mdContent, options)\n      },\n\n      insertContent: (value, options?: MarkdownInsertContentOptions) => {\n        // if no contentType is specified, we assume the content is in JSON format OR HTML format\n        if (!options?.contentType) {\n          return commands.insertContent(value, options)\n        }\n\n        const actualContentType = assumeContentType(value, options?.contentType)\n\n        if (actualContentType !== 'markdown' || !this.editor.markdown) {\n          return commands.insertContent(value, options)\n        }\n\n        const mdContent = this.editor.markdown.parse(value as string)\n        return commands.insertContent(mdContent, options)\n      },\n\n      insertContentAt: (position, value, options?: MarkdownInsertContentAtOptions) => {\n        // if no contentType is specified, we assume the content is in JSON format OR HTML format\n        if (!options?.contentType) {\n          return commands.insertContentAt(position, value, options)\n        }\n\n        const actualContentType = assumeContentType(value, options?.contentType)\n\n        if (actualContentType !== 'markdown' || !this.editor.markdown) {\n          return commands.insertContentAt(position, value, options)\n        }\n\n        const mdContent = this.editor.markdown.parse(value as string)\n        return commands.insertContentAt(position, mdContent, options)\n      },\n    }\n  },\n\n  addStorage() {\n    return {\n      manager: new MarkdownManager({\n        indentation: this.options.indentation,\n        marked: this.options.marked,\n        markedOptions: this.options.markedOptions,\n        extensions: [],\n      }),\n    }\n  },\n\n  onBeforeCreate() {\n    if (this.editor.markdown) {\n      console.error(\n        '[tiptap][markdown]: There is already a `markdown` property on the editor instance. This might lead to unexpected behavior.',\n      )\n      return\n    }\n\n    this.storage.manager = new MarkdownManager({\n      indentation: this.options.indentation,\n      marked: this.options.marked,\n      markedOptions: this.options.markedOptions,\n      extensions: this.editor.extensionManager.baseExtensions,\n    })\n\n    this.editor.markdown = this.storage.manager\n\n    // add a `getMarkdown()` method to the editor\n    this.editor.getMarkdown = () => {\n      return this.storage.manager.serialize(this.editor.getJSON())\n    }\n\n    if (!this.editor.options.contentType) {\n      return\n    }\n\n    const assumedType = assumeContentType(this.editor.options.content, this.editor.options.contentType)\n    if (assumedType !== 'markdown') {\n      return\n    }\n\n    if (!this.editor.markdown) {\n      throw new Error(\n        '[tiptap][markdown]: The `contentType` option is set to \"markdown\", but the Markdown extension is not added to the editor. Please add the Markdown extension to use this feature.',\n      )\n    }\n\n    if (this.editor.options.content === undefined || typeof this.editor.options.content !== 'string') {\n      throw new Error(\n        '[tiptap][markdown]: The `contentType` option is set to \"markdown\", but the initial content is not a string. Please provide the initial content as a markdown string.',\n      )\n    }\n\n    const json = this.editor.markdown.parse(this.editor.options.content as string)\n    this.editor.options.content = json\n  },\n})\n","import {\n  type AnyExtension,\n  type ExtendableConfig,\n  type JSONContent,\n  type MarkdownExtensionSpec,\n  type MarkdownParseHelpers,\n  type MarkdownParseResult,\n  type MarkdownRendererHelpers,\n  type MarkdownToken,\n  type MarkdownTokenizer,\n  type RenderContext,\n  flattenExtensions,\n  generateJSON,\n  getExtensionField,\n} from '@tiptap/core'\nimport { type Lexer, type Token, type TokenizerExtension, marked } from 'marked'\n\nimport {\n  closeMarksBeforeNode,\n  findMarksToClose,\n  findMarksToCloseAtEnd,\n  findMarksToOpen,\n  isTaskItem,\n  reopenMarksAfterNode,\n  wrapInMarkdownBlock,\n} from './utils.js'\n\nexport class MarkdownManager {\n  private markedInstance: typeof marked\n  private lexer: Lexer\n  private registry: Map<string, MarkdownExtensionSpec[]>\n  private nodeTypeRegistry: Map<string, MarkdownExtensionSpec[]>\n  private indentStyle: 'space' | 'tab'\n  private indentSize: number\n  private baseExtensions: AnyExtension[] = []\n  private extensions: AnyExtension[] = []\n\n  /**\n   * Create a MarkdownManager.\n   * @param options.marked Optional marked instance to use (injected).\n   * @param options.markedOptions Optional options to pass to marked.setOptions\n   * @param options.indentation Indentation settings (style and size).\n   * @param options.extensions An array of Tiptap extensions to register for markdown parsing and rendering.\n   */\n  constructor(options?: {\n    marked?: typeof marked\n    markedOptions?: Parameters<typeof marked.setOptions>[0]\n    indentation?: { style?: 'space' | 'tab'; size?: number }\n    extensions: AnyExtension[]\n  }) {\n    this.markedInstance = options?.marked ?? marked\n    this.lexer = new this.markedInstance.Lexer()\n    this.indentStyle = options?.indentation?.style ?? 'space'\n    this.indentSize = options?.indentation?.size ?? 2\n    this.baseExtensions = options?.extensions || []\n\n    if (options?.markedOptions && typeof this.markedInstance.setOptions === 'function') {\n      this.markedInstance.setOptions(options.markedOptions)\n    }\n\n    this.registry = new Map()\n    this.nodeTypeRegistry = new Map()\n\n    // If extensions were provided, register them now\n    if (options?.extensions) {\n      this.baseExtensions = options.extensions\n      const flattened = flattenExtensions(options.extensions)\n      flattened.forEach(ext => this.registerExtension(ext, false))\n    }\n    this.lexer = new this.markedInstance.Lexer() // Reset lexer to include all tokenizers\n  }\n\n  /** Returns the underlying marked instance. */\n  get instance(): typeof marked {\n    return this.markedInstance\n  }\n\n  /** Returns the correct indentCharacter (space or tab) */\n  get indentCharacter(): string {\n    return this.indentStyle === 'space' ? ' ' : '\\t'\n  }\n\n  /** Returns the correct indentString repeated X times */\n  get indentString(): string {\n    return this.indentCharacter.repeat(this.indentSize)\n  }\n\n  /** Helper to quickly check whether a marked instance is available. */\n  hasMarked(): boolean {\n    return !!this.markedInstance\n  }\n\n  /**\n   * Register a Tiptap extension (Node/Mark/Extension). This will read\n   * `markdownName`, `parseMarkdown`, `renderMarkdown` and `priority` from the\n   * extension config (using the same resolution used across the codebase).\n   */\n  registerExtension(extension: AnyExtension, recreateLexer: boolean = true): void {\n    // Keep track of all extensions for HTML parsing\n    this.extensions.push(extension)\n\n    const name = extension.name\n    const tokenName =\n      (getExtensionField(extension, 'markdownTokenName') as ExtendableConfig['markdownTokenName']) || name\n    const parseMarkdown = getExtensionField(extension, 'parseMarkdown') as ExtendableConfig['parseMarkdown'] | undefined\n    const renderMarkdown = getExtensionField(extension, 'renderMarkdown') as\n      | ExtendableConfig['renderMarkdown']\n      | undefined\n    const tokenizer = getExtensionField(extension, 'markdownTokenizer') as\n      | ExtendableConfig['markdownTokenizer']\n      | undefined\n\n    // Read the `markdown` object from the extension config. This allows\n    // extensions to provide `markdown: { name?, parseName?, renderName?, parse?, render?, match? }`.\n    const markdownCfg = (getExtensionField(extension, 'markdownOptions') ?? null) as ExtendableConfig['markdownOptions']\n    const isIndenting = markdownCfg?.indentsContent ?? false\n    const htmlReopen = markdownCfg?.htmlReopen\n\n    const spec: MarkdownExtensionSpec = {\n      tokenName,\n      nodeName: name,\n      parseMarkdown,\n      renderMarkdown,\n      isIndenting,\n      htmlReopen,\n      tokenizer,\n    }\n\n    // Add to parse registry using parseName\n    if (tokenName && parseMarkdown) {\n      const parseExisting = this.registry.get(tokenName) || []\n      parseExisting.push(spec)\n      this.registry.set(tokenName, parseExisting)\n    }\n\n    // Add to render registry using renderName (node type)\n    if (renderMarkdown) {\n      const renderExisting = this.nodeTypeRegistry.get(name) || []\n      renderExisting.push(spec)\n      this.nodeTypeRegistry.set(name, renderExisting)\n    }\n\n    // Register custom tokenizer with marked.js\n    if (tokenizer && this.hasMarked()) {\n      this.registerTokenizer(tokenizer)\n\n      if (recreateLexer) {\n        this.lexer = new this.markedInstance.Lexer() // Reset lexer to include new tokenizer\n      }\n    }\n  }\n\n  /**\n   * Register a custom tokenizer with marked.js for parsing non-standard markdown syntax.\n   */\n  private registerTokenizer(tokenizer: MarkdownTokenizer): void {\n    if (!this.hasMarked()) {\n      return\n    }\n\n    const { name, start, level = 'inline', tokenize } = tokenizer\n\n    // Helper functions that use a fresh lexer instance with all registered extensions\n    const tokenizeInline = (src: string) => {\n      return this.lexer.inlineTokens(src)\n    }\n\n    const tokenizeBlock = (src: string) => {\n      return this.lexer.blockTokens(src)\n    }\n\n    const helper = {\n      inlineTokens: tokenizeInline,\n      blockTokens: tokenizeBlock,\n    }\n\n    let startCb: (src: string) => number\n\n    if (!start) {\n      startCb = (src: string) => {\n        // For other tokenizers, try to find a match and return its position\n        const result = tokenize(src, [], helper)\n        if (result && result.raw) {\n          const index = src.indexOf(result.raw)\n          return index\n        }\n        return -1\n      }\n    } else {\n      startCb = typeof start === 'function' ? start : (src: string) => src.indexOf(start)\n    }\n\n    // Create marked.js extension with proper types\n    const markedExtension: TokenizerExtension = {\n      name,\n      level,\n      start: startCb,\n      tokenizer: (src, tokens) => {\n        const result = tokenize(src, tokens, helper)\n\n        if (result && result.type) {\n          return {\n            ...result,\n            type: result.type || name,\n            raw: result.raw || '',\n            tokens: (result.tokens || []) as Token[],\n          }\n        }\n\n        return undefined\n      },\n      childTokens: [],\n    }\n\n    // Register with marked.js - use extensions array to control priority\n    this.markedInstance.use({\n      extensions: [markedExtension],\n    })\n  }\n\n  /** Get registered handlers for a token type and try each until one succeeds. */\n  private getHandlersForToken(type: string): MarkdownExtensionSpec[] {\n    try {\n      return this.registry.get(type) || []\n    } catch {\n      return []\n    }\n  }\n\n  /** Get the first handler for a token type (for backwards compatibility). */\n  private getHandlerForToken(type: string): MarkdownExtensionSpec | undefined {\n    // First try the markdown token registry (for parsing)\n    const markdownHandlers = this.getHandlersForToken(type)\n    if (markdownHandlers.length > 0) {\n      return markdownHandlers[0]\n    }\n\n    // Then try the node type registry (for rendering)\n    const nodeTypeHandlers = this.getHandlersForNodeType(type)\n    return nodeTypeHandlers.length > 0 ? nodeTypeHandlers[0] : undefined\n  }\n\n  /** Get registered handlers for a node type (for rendering). */\n  private getHandlersForNodeType(type: string): MarkdownExtensionSpec[] {\n    try {\n      return this.nodeTypeRegistry.get(type) || []\n    } catch {\n      return []\n    }\n  }\n\n  /**\n   * Serialize a ProseMirror-like JSON document (or node array) to a Markdown string\n   * using registered renderers and fallback renderers.\n   */\n  serialize(docOrContent: JSONContent): string {\n    if (!docOrContent) {\n      return ''\n    }\n\n    const result = this.renderNodes(docOrContent, docOrContent)\n    // Return empty string if result is only whitespace entities or non-breaking spaces\n    return this.isEmptyOutput(result) ? '' : result\n  }\n\n  /**\n   * Check if the markdown output represents an empty document.\n   * Empty documents may contain only &nbsp; entities or non-breaking space characters\n   * which are used by the Paragraph extension to preserve blank lines.\n   */\n  private isEmptyOutput(markdown: string): boolean {\n    if (!markdown || markdown.trim() === '') {\n      return true\n    }\n\n    // Check if the output is only &nbsp; entities or non-breaking space characters\n    const cleanedOutput = markdown\n      .replace(/&nbsp;/g, '')\n      .replace(/\\u00A0/g, '')\n      .trim()\n    return cleanedOutput === ''\n  }\n\n  /**\n   * Parse markdown string into Tiptap JSON document using registered extension handlers.\n   */\n  parse(markdown: string): JSONContent {\n    if (!this.hasMarked()) {\n      throw new Error('No marked instance available for parsing')\n    }\n\n    // Use marked to tokenize the markdown\n    const tokens = this.markedInstance.lexer(markdown)\n\n    // Convert tokens to Tiptap JSON\n    const content = this.parseTokens(tokens, true)\n\n    // Return a document node containing the parsed content\n    return {\n      type: 'doc',\n      content,\n    }\n  }\n\n  /**\n   * Convert an array of marked tokens into Tiptap JSON nodes using registered extension handlers.\n   */\n  private parseTokens(tokens: MarkdownToken[], parseImplicitEmptyParagraphs = false): JSONContent[] {\n    const nonSpaceTokenIndexes = tokens.reduce<number[]>((indexes, token, index) => {\n      if (token.type !== 'space') {\n        indexes.push(index)\n      }\n\n      return indexes\n    }, [])\n\n    let previousNonSpaceTokenIndex = -1\n    let nextNonSpaceTokenPointer = 0\n\n    return tokens.flatMap((token, index) => {\n      while (\n        nextNonSpaceTokenPointer < nonSpaceTokenIndexes.length &&\n        nonSpaceTokenIndexes[nextNonSpaceTokenPointer] < index\n      ) {\n        previousNonSpaceTokenIndex = nonSpaceTokenIndexes[nextNonSpaceTokenPointer]\n        nextNonSpaceTokenPointer += 1\n      }\n\n      if (parseImplicitEmptyParagraphs && token.type === 'space') {\n        const nextNonSpaceTokenIndex = nonSpaceTokenIndexes[nextNonSpaceTokenPointer] ?? -1\n\n        return this.createImplicitEmptyParagraphsFromSpace(token, previousNonSpaceTokenIndex, nextNonSpaceTokenIndex)\n      }\n\n      const parsed = this.parseToken(token, parseImplicitEmptyParagraphs)\n\n      if (parsed === null) {\n        return []\n      }\n\n      return Array.isArray(parsed) ? parsed : [parsed]\n    })\n  }\n\n  private createImplicitEmptyParagraphsFromSpace(\n    token: MarkdownToken,\n    previousNonSpaceTokenIndex: number,\n    nextNonSpaceTokenIndex: number,\n  ): JSONContent[] {\n    const separatorCount = this.countParagraphSeparators(token.raw || '')\n\n    if (separatorCount === 0) {\n      return []\n    }\n\n    const isBoundarySpace = previousNonSpaceTokenIndex === -1 || nextNonSpaceTokenIndex === -1\n    const emptyParagraphCount = Math.max(separatorCount - (isBoundarySpace ? 0 : 1), 0)\n\n    return Array.from({ length: emptyParagraphCount }, () => ({ type: 'paragraph', content: [] }))\n  }\n\n  private countParagraphSeparators(raw: string): number {\n    return (raw.replace(/\\r\\n/g, '\\n').match(/\\n\\n/g) || []).length\n  }\n\n  /**\n   * Parse a single token into Tiptap JSON using the appropriate registered handler.\n   */\n  private parseToken(token: MarkdownToken, parseImplicitEmptyParagraphs = false): JSONContent | JSONContent[] | null {\n    if (!token.type) {\n      return null\n    }\n\n    // Special handling for 'list' tokens that may contain mixed bullet/task items\n    if (token.type === 'list') {\n      return this.parseListToken(token)\n    }\n\n    const handlers = this.getHandlersForToken(token.type)\n    const helpers = this.createParseHelpers()\n\n    // Try each handler until one returns a valid result\n    const result = handlers.find(handler => {\n      if (!handler.parseMarkdown) {\n        return false\n      }\n\n      const parseResult = handler.parseMarkdown(token, helpers)\n      const normalized = this.normalizeParseResult(parseResult)\n\n      // Check if this handler returned a valid result (not null/empty array)\n      if (normalized && (!Array.isArray(normalized) || normalized.length > 0)) {\n        // Store result for return\n        this.lastParseResult = normalized\n        return true\n      }\n\n      return false\n    })\n\n    // If a handler worked, return its result\n    if (result && this.lastParseResult) {\n      const toReturn = this.lastParseResult\n      this.lastParseResult = null // Clean up\n      return toReturn\n    }\n\n    // If no handler worked, try fallback parsing\n    return this.parseFallbackToken(token, parseImplicitEmptyParagraphs)\n  }\n\n  private lastParseResult: JSONContent | JSONContent[] | null = null\n\n  /**\n   * Parse a list token, handling mixed bullet and task list items by splitting them into separate lists.\n   * This ensures that consecutive task items and bullet items are grouped and parsed as separate list nodes.\n   *\n   * @param token The list token to parse\n   * @returns Array of parsed list nodes, or null if parsing fails\n   */\n  private parseListToken(token: MarkdownToken): JSONContent | JSONContent[] | null {\n    if (!token.items || token.items.length === 0) {\n      // No items, parse normally\n      return this.parseTokenWithHandlers(token)\n    }\n\n    const hasTask = token.items.some(item => isTaskItem(item).isTask)\n    const hasNonTask = token.items.some(item => !isTaskItem(item).isTask)\n\n    if (!hasTask || !hasNonTask || this.getHandlersForToken('taskList').length === 0) {\n      // Not mixed or no taskList extension, parse normally\n      return this.parseTokenWithHandlers(token)\n    }\n\n    // Mixed list with taskList extension available: split into separate lists\n    type TaskListItemToken = MarkdownToken & { type: 'taskItem'; checked?: boolean; indentLevel?: number }\n    const groups: { type: 'list' | 'taskList'; items: (MarkdownToken | TaskListItemToken)[] }[] = []\n    let currentGroup: (MarkdownToken | TaskListItemToken)[] = []\n    let currentType: 'list' | 'taskList' | null = null\n\n    for (let i = 0; i < token.items.length; i += 1) {\n      const item = token.items[i]\n      const { isTask, checked, indentLevel } = isTaskItem(item)\n      let processedItem = item\n\n      if (isTask) {\n        // Transform list_item into taskItem token\n        const raw = item.raw || item.text || ''\n\n        // Split raw content by lines to separate main content from nested\n        const lines = raw.split('\\n')\n\n        // Extract main content from the first line\n        const firstLineMatch = lines[0].match(/^\\s*[-+*]\\s+\\[([ xX])\\]\\s+(.*)$/)\n        const mainContent = firstLineMatch ? firstLineMatch[2] : ''\n\n        // Parse nested content from remaining lines\n        let nestedTokens: MarkdownToken[] = []\n        if (lines.length > 1) {\n          // Join all lines after the first\n          const nestedRaw = lines.slice(1).join('\\n')\n\n          // Only parse if there's actual content\n          if (nestedRaw.trim()) {\n            // Find minimum indentation of non-empty lines\n            const nestedLines = lines.slice(1)\n            const nonEmptyLines = nestedLines.filter(line => line.trim())\n            if (nonEmptyLines.length > 0) {\n              const minIndent = Math.min(...nonEmptyLines.map(line => line.length - line.trimStart().length))\n              // Remove common indentation while preserving structure\n              const trimmedLines = nestedLines.map(line => {\n                if (!line.trim()) {\n                  return '' // Keep empty lines\n                }\n                return line.slice(minIndent)\n              })\n              const nestedContent = trimmedLines.join('\\n').trim()\n              // Use the lexer to parse nested content\n              if (nestedContent) {\n                // Use the full lexer pipeline to ensure inline tokens are populated\n                nestedTokens = this.markedInstance.lexer(`${nestedContent}\\n`)\n              }\n            }\n          }\n        }\n\n        processedItem = {\n          type: 'taskItem',\n          raw: '',\n          mainContent,\n          indentLevel,\n          checked: checked ?? false,\n          text: mainContent,\n          tokens: this.lexer.inlineTokens(mainContent),\n          nestedTokens,\n        }\n      }\n\n      const itemType: 'list' | 'taskList' = isTask ? 'taskList' : 'list'\n\n      if (currentType !== itemType) {\n        if (currentGroup.length > 0) {\n          groups.push({ type: currentType!, items: currentGroup })\n        }\n        currentGroup = [processedItem]\n        currentType = itemType\n      } else {\n        currentGroup.push(processedItem)\n      }\n    }\n\n    if (currentGroup.length > 0) {\n      groups.push({ type: currentType!, items: currentGroup })\n    }\n\n    // Parse each group as a separate token\n    const results: JSONContent[] = []\n    for (let i = 0; i < groups.length; i += 1) {\n      const group = groups[i]\n      const subToken = { ...token, type: group.type, items: group.items }\n      const parsed = this.parseToken(subToken)\n      if (parsed) {\n        if (Array.isArray(parsed)) {\n          results.push(...parsed)\n        } else {\n          results.push(parsed)\n        }\n      }\n    }\n\n    return results.length > 0 ? results : null\n  }\n\n  /**\n   * Parse a token using registered handlers (extracted for reuse).\n   */\n  private parseTokenWithHandlers(token: MarkdownToken): JSONContent | JSONContent[] | null {\n    if (!token.type) {\n      return null\n    }\n\n    const handlers = this.getHandlersForToken(token.type)\n    const helpers = this.createParseHelpers()\n\n    // Try each handler until one returns a valid result\n    const result = handlers.find(handler => {\n      if (!handler.parseMarkdown) {\n        return false\n      }\n\n      const parseResult = handler.parseMarkdown(token, helpers)\n      const normalized = this.normalizeParseResult(parseResult)\n\n      // Check if this handler returned a valid result (not null/empty array)\n      if (normalized && (!Array.isArray(normalized) || normalized.length > 0)) {\n        // Store result for return\n        this.lastParseResult = normalized\n        return true\n      }\n\n      return false\n    })\n\n    // If a handler worked, return its result\n    if (result && this.lastParseResult) {\n      const toReturn = this.lastParseResult\n      this.lastParseResult = null // Clean up\n      return toReturn\n    }\n\n    // If no handler worked, try fallback parsing\n    return this.parseFallbackToken(token)\n  }\n\n  /**\n   * Creates helper functions for parsing markdown tokens.\n   * @returns An object containing helper functions for parsing.\n   */\n  private createParseHelpers(): MarkdownParseHelpers {\n    return {\n      parseInline: (tokens: MarkdownToken[]) => this.parseInlineTokens(tokens),\n      parseChildren: (tokens: MarkdownToken[]) => this.parseTokens(tokens),\n      parseBlockChildren: (tokens: MarkdownToken[]) => this.parseTokens(tokens, true),\n      createTextNode: (text: string, marks?: Array<{ type: string; attrs?: any }>) => {\n        const node = {\n          type: 'text',\n          text,\n          marks: marks || undefined,\n        }\n\n        return node\n      },\n      createNode: (type: string, attrs?: any, content?: JSONContent[]) => {\n        const node = {\n          type,\n          attrs: attrs || undefined,\n          content: content || undefined,\n        }\n\n        if (!attrs || Object.keys(attrs).length === 0) {\n          delete node.attrs\n        }\n\n        return node\n      },\n      applyMark: (markType: string, content: JSONContent[], attrs?: any) => ({\n        mark: markType,\n        content,\n        attrs: attrs && Object.keys(attrs).length > 0 ? attrs : undefined,\n      }),\n    }\n  }\n\n  /**\n   * Escape special regex characters in a string.\n   */\n  private escapeRegex(str: string): string {\n    return str.replace(/[.*+?^${}()|[\\]\\\\]/g, '\\\\$&')\n  }\n\n  /**\n   * Parse inline tokens (bold, italic, links, etc.) into text nodes with marks.\n   * This is the complex part that handles mark nesting and boundaries.\n   */\n  private parseInlineTokens(tokens: MarkdownToken[]): JSONContent[] {\n    const result: JSONContent[] = []\n\n    // Process tokens sequentially using an index so we can lookahead and\n    // merge split inline HTML fragments like: text / <em> / inner / </em> / text\n    for (let i = 0; i < tokens.length; i += 1) {\n      const token = tokens[i]\n\n      if (token.type === 'text') {\n        result.push({\n          type: 'text',\n          text: token.text || '',\n        })\n      } else if (token.type === 'html') {\n        // Handle possible split inline HTML by attempting to detect an\n        // opening tag and searching forward for a matching closing tag.\n        const raw = (token.raw ?? token.text ?? '').toString()\n\n        // Quick checks for opening vs. closing tag\n        const isClosing = /^<\\/[\\s]*[\\w-]+/i.test(raw)\n        const openMatch = raw.match(/^<[\\s]*([\\w-]+)(\\s|>|\\/|$)/i)\n\n        if (!isClosing && openMatch && !/\\/>$/.test(raw)) {\n          // Try to find the corresponding closing html token for this tag\n          const tagName = openMatch[1]\n          const escapedTagName = this.escapeRegex(tagName)\n          const closingRegex = new RegExp(`^<\\\\/\\\\s*${escapedTagName}\\\\b`, 'i')\n          let foundIndex = -1\n\n          // Collect intermediate raw parts to reconstruct full HTML fragment\n          const parts: string[] = [raw]\n          for (let j = i + 1; j < tokens.length; j += 1) {\n            const t = tokens[j]\n            const tRaw = (t.raw ?? t.text ?? '').toString()\n            parts.push(tRaw)\n            if (t.type === 'html' && closingRegex.test(tRaw)) {\n              foundIndex = j\n              break\n            }\n          }\n\n          if (foundIndex !== -1) {\n            // Merge opening + inner + closing into one html fragment and parse\n            const mergedRaw = parts.join('')\n            const mergedToken = {\n              type: 'html',\n              raw: mergedRaw,\n              text: mergedRaw,\n              block: false,\n            } as unknown as MarkdownToken\n\n            const parsed = this.parseHTMLToken(mergedToken)\n            if (parsed) {\n              const normalized = this.normalizeParseResult(parsed as any)\n              if (Array.isArray(normalized)) {\n                result.push(...normalized)\n              } else if (normalized) {\n                result.push(normalized)\n              }\n            }\n\n            // Advance i to the closing token\n            i = foundIndex\n            continue\n          }\n        }\n\n        // Fallback: single html token parse\n        const parsedSingle = this.parseHTMLToken(token)\n        if (parsedSingle) {\n          const normalized = this.normalizeParseResult(parsedSingle as any)\n          if (Array.isArray(normalized)) {\n            result.push(...normalized)\n          } else if (normalized) {\n            result.push(normalized)\n          }\n        }\n      } else if (token.type) {\n        // Handle inline marks (bold, italic, etc.)\n        const markHandler = this.getHandlerForToken(token.type)\n        if (markHandler && markHandler.parseMarkdown) {\n          const helpers = this.createParseHelpers()\n          const parsed = markHandler.parseMarkdown(token, helpers)\n\n          if (this.isMarkResult(parsed)) {\n            // This is a mark result - apply the mark to the content\n            const markedContent = this.applyMarkToContent(parsed.mark, parsed.content, parsed.attrs)\n            result.push(...markedContent)\n          } else {\n            // Regular inline node\n            const normalized = this.normalizeParseResult(parsed)\n            if (Array.isArray(normalized)) {\n              result.push(...normalized)\n            } else if (normalized) {\n              result.push(normalized)\n            }\n          }\n        } else if (token.tokens) {\n          // Fallback: try to parse children if they exist\n          result.push(...this.parseInlineTokens(token.tokens))\n        }\n      }\n    }\n\n    return result\n  }\n\n  /**\n   * Apply a mark to content nodes.\n   */\n  private applyMarkToContent(markType: string, content: JSONContent[], attrs?: any): JSONContent[] {\n    return content.map(node => {\n      if (node.type === 'text') {\n        // Add the mark to existing marks or create new marks array\n        const existingMarks = node.marks || []\n        const newMark = attrs ? { type: markType, attrs } : { type: markType }\n        return {\n          ...node,\n          marks: [...existingMarks, newMark],\n        }\n      }\n\n      // For non-text nodes, recursively apply to content\n      return {\n        ...node,\n        content: node.content ? this.applyMarkToContent(markType, node.content, attrs) : undefined,\n      }\n    })\n  } /**\n   * Check if a parse result represents a mark to be applied.\n   */\n  private isMarkResult(result: any): result is { mark: string; content: JSONContent[]; attrs?: any } {\n    return result && typeof result === 'object' && 'mark' in result\n  }\n\n  /**\n   * Normalize parse results to ensure they're valid JSONContent.\n   */\n  private normalizeParseResult(result: MarkdownParseResult): JSONContent | JSONContent[] | null {\n    if (!result) {\n      return null\n    }\n\n    if (this.isMarkResult(result)) {\n      // This shouldn't happen at the top level, but handle it gracefully\n      return result.content\n    }\n\n    return result as JSONContent | JSONContent[]\n  }\n\n  /**\n   * Fallback parsing for common tokens when no specific handler is registered.\n   */\n  private parseFallbackToken(\n    token: MarkdownToken,\n    parseImplicitEmptyParagraphs = false,\n  ): JSONContent | JSONContent[] | null {\n    switch (token.type) {\n      case 'paragraph':\n        return {\n          type: 'paragraph',\n          content: token.tokens ? this.parseInlineTokens(token.tokens) : [],\n        }\n\n      case 'heading':\n        return {\n          type: 'heading',\n          attrs: { level: token.depth || 1 },\n          content: token.tokens ? this.parseInlineTokens(token.tokens) : [],\n        }\n\n      case 'text':\n        return {\n          type: 'text',\n          text: token.text || '',\n        }\n\n      case 'html':\n        // Parse HTML using extensions' parseHTML methods\n        return this.parseHTMLToken(token)\n\n      case 'space':\n        return null\n\n      default:\n        // Unknown token type - try to parse children if they exist\n        if (token.tokens) {\n          return this.parseTokens(token.tokens, parseImplicitEmptyParagraphs)\n        }\n        return null\n    }\n  }\n\n  /**\n   * Parse HTML tokens using extensions' parseHTML methods.\n   * This allows HTML within markdown to be parsed according to extension rules.\n   */\n  private parseHTMLToken(token: MarkdownToken): JSONContent | JSONContent[] | null {\n    const html = token.text || token.raw || ''\n\n    if (!html.trim()) {\n      return null\n    }\n\n    // Check if we're in a server-side environment (no window object)\n    // If so, fall back to treating HTML as plain text to avoid runtime errors\n    if (typeof window === 'undefined') {\n      // For block-level HTML, wrap in a paragraph to maintain valid document structure\n      if (token.block) {\n        return {\n          type: 'paragraph',\n          content: [\n            {\n              type: 'text',\n              text: html,\n            },\n          ],\n        }\n      }\n      // For inline HTML, return plain text\n      return {\n        type: 'text',\n        text: html,\n      }\n    }\n\n    // Use generateJSON to parse the HTML using extensions' parseHTML rules\n    try {\n      const parsed = generateJSON(html, this.baseExtensions)\n\n      // If the result is a doc node, extract its content\n      if (parsed.type === 'doc' && parsed.content) {\n        // For block-level HTML, return the content array\n        if (token.block) {\n          return parsed.content\n        }\n\n        // For inline HTML, we need to flatten the content appropriately\n        // If there's only one paragraph with content, unwrap it\n        if (parsed.content.length === 1 && parsed.content[0].type === 'paragraph' && parsed.content[0].content) {\n          return parsed.content[0].content\n        }\n\n        return parsed.content\n      }\n\n      return parsed as JSONContent\n    } catch (error) {\n      throw new Error(`Failed to parse HTML in markdown: ${error}`)\n    }\n  }\n\n  renderNodeToMarkdown(\n    node: JSONContent,\n    parentNode?: JSONContent,\n    index = 0,\n    level = 0,\n    meta: Record<string, any> = {},\n  ): string {\n    // if node is a text node, we simply return it's text content\n    // marks are handled at the array level in renderNodesWithMarkBoundaries\n    if (node.type === 'text') {\n      return node.text || ''\n    }\n\n    if (!node.type) {\n      return ''\n    }\n\n    const handler = this.getHandlerForToken(node.type)\n    if (!handler) {\n      return ''\n    }\n\n    const previousNode = Array.isArray(parentNode?.content) && index > 0 ? parentNode.content[index - 1] : undefined\n    const helpers: MarkdownRendererHelpers = {\n      renderChildren: (nodes, separator) => {\n        const childLevel = handler.isIndenting ? level + 1 : level\n\n        if (!Array.isArray(nodes) && (nodes as any).content) {\n          return this.renderNodes((nodes as any).content as JSONContent[], node, separator || '', index, childLevel)\n        }\n\n        return this.renderNodes(nodes, node, separator || '', index, childLevel)\n      },\n      renderChild: (childNode, childIndex) => {\n        const childLevel = handler.isIndenting ? level + 1 : level\n\n        return this.renderNodeToMarkdown(childNode, node, childIndex, childLevel)\n      },\n      indent: content => {\n        return this.indentString + content\n      },\n      wrapInBlock: wrapInMarkdownBlock,\n    }\n\n    const context: RenderContext = {\n      index,\n      level,\n      parentType: parentNode?.type,\n      previousNode,\n      meta: {\n        parentAttrs: parentNode?.attrs,\n        ...meta,\n      },\n    }\n\n    // First render the node itself (this will render children recursively)\n    const rendered = handler.renderMarkdown?.(node, helpers, context) || ''\n\n    return rendered\n  }\n\n  /**\n   * Render a node or an array of nodes. Parent type controls how children\n   * are joined (which determines newline insertion between children).\n   */\n  renderNodes(\n    nodeOrNodes: JSONContent | JSONContent[],\n    parentNode?: JSONContent,\n    separator = '',\n    index = 0,\n    level = 0,\n  ): string {\n    // if we have just one node, call renderNodeToMarkdown directly\n    if (!Array.isArray(nodeOrNodes)) {\n      if (!nodeOrNodes.type) {\n        return ''\n      }\n\n      return this.renderNodeToMarkdown(nodeOrNodes, parentNode, index, level)\n    }\n\n    return this.renderNodesWithMarkBoundaries(nodeOrNodes, parentNode, separator, level)\n  }\n\n  /**\n   * Render an array of nodes while properly tracking mark boundaries.\n   * This handles cases where marks span across multiple text nodes.\n   */\n  private renderNodesWithMarkBoundaries(\n    nodes: JSONContent[],\n    parentNode?: JSONContent,\n    separator = '',\n    level = 0,\n  ): string {\n    const result: string[] = []\n    const activeMarks: Map<string, any> = new Map()\n    const reopenWithHtmlOnNextOpen = new Set<string>()\n    const markOpeningModes = new Map<string, 'markdown' | 'html'>()\n    nodes.forEach((node, i) => {\n      // Lookahead to the next node to determine if marks need to be closed\n      const nextNode = i < nodes.length - 1 ? nodes[i + 1] : null\n\n      if (!node.type) {\n        return\n      }\n\n      if (node.type === 'text') {\n        let textContent = node.text || ''\n        const currentMarks = new Map((node.marks || []).map(mark => [mark.type, mark]))\n\n        // Find marks that need to be closed and opened\n        const marksToOpen = findMarksToOpen(activeMarks, currentMarks)\n        const marksToClose = findMarksToClose(currentMarks, nextNode)\n\n        // When marks simultaneously close (old) AND open (new) at this boundary, the naive\n        // approach of appending old-close and prepending new-open produces interleaved\n        // delimiters like `*456**` (italic open, text, bold close) instead of properly\n        // nested `_456_**` (italic open, text, italic close, bold close).\n        //\n        // The fix: when both are present, defer old mark closings to the end of the node\n        // (after the new marks also close), ensuring correct inner-before-outer order.\n        //\n        // If an already-active mark ends on this node while another mark opens on this same\n        // node, we defer closing the active mark until the end of the node so nesting stays\n        // valid (`**...++abc++**` instead of `**...++abc**++`).\n        const activeMarksClosingHere = marksToClose.filter(markType => activeMarks.has(markType))\n        const hasCrossedBoundary = activeMarksClosingHere.length > 0 && marksToOpen.length > 0\n\n        let middleTrailingWhitespace = ''\n\n        if (marksToClose.length > 0 && !hasCrossedBoundary) {\n          // Extract trailing whitespace before closing marks to prevent invalid markdown like \"**text **\"\n          const middleTrailingMatch = textContent.match(/(\\s+)$/)\n          if (middleTrailingMatch) {\n            middleTrailingWhitespace = middleTrailingMatch[1]\n            textContent = textContent.slice(0, -middleTrailingWhitespace.length)\n          }\n        }\n\n        if (!hasCrossedBoundary) {\n          // Normal path: close marks that are ending here (no new marks opening simultaneously)\n          marksToClose.forEach(markType => {\n            if (!activeMarks.has(markType)) {\n              return\n            }\n\n            const mark = currentMarks.get(markType)\n            const closeMarkdown = this.getMarkClosing(markType, mark, markOpeningModes.get(markType))\n            if (closeMarkdown) {\n              textContent += closeMarkdown\n            }\n            if (activeMarks.has(markType)) {\n              activeMarks.delete(markType)\n              markOpeningModes.delete(markType)\n            }\n          })\n        }\n\n        // Open new marks (should be at the beginning)\n        // Extract leading whitespace before opening marks to prevent invalid markdown like \"** text**\"\n        let leadingWhitespace = ''\n        if (marksToOpen.length > 0) {\n          const leadingMatch = textContent.match(/^(\\s+)/)\n          if (leadingMatch) {\n            leadingWhitespace = leadingMatch[1]\n            textContent = textContent.slice(leadingWhitespace.length)\n          }\n        }\n\n        // Snapshot active mark types before opening new marks, so each new mark's delimiter\n        // is chosen based on what is already active (not including itself).\n        // When crossing a boundary, old marks are still in activeMarks here (not yet removed),\n        // so new marks correctly see them as active context.\n        marksToOpen.forEach(({ type, mark }) => {\n          const openingMode = reopenWithHtmlOnNextOpen.has(type) ? 'html' : 'markdown'\n          const openMarkdown = this.getMarkOpening(type, mark, openingMode)\n          if (openMarkdown) {\n            textContent = openMarkdown + textContent\n          }\n          markOpeningModes.set(type, openingMode)\n          reopenWithHtmlOnNextOpen.delete(type)\n        })\n\n        if (!hasCrossedBoundary) {\n          marksToOpen\n            .slice()\n            .reverse()\n            .forEach(({ type, mark }) => {\n              activeMarks.set(type, mark)\n            })\n        }\n\n        // Add leading whitespace before the mark opening\n        textContent = leadingWhitespace + textContent\n\n        // Determine marks to close at the end of this node.\n        // On a crossed boundary, we close new marks (inner) first, then old marks (outer),\n        // ensuring correct nesting order. Both sets are removed from activeMarks so the\n        // next node's marksToOpen will reopen whichever ones continue.\n        let marksToCloseAtEnd: string[]\n        if (hasCrossedBoundary) {\n          const nextMarkTypes = new Set((nextNode?.marks || []).map((mark: any) => mark.type))\n\n          marksToOpen.forEach(({ type }) => {\n            if (nextMarkTypes.has(type) && this.getHtmlReopenTags(type)) {\n              reopenWithHtmlOnNextOpen.add(type)\n            }\n          })\n\n          marksToCloseAtEnd = [\n            ...marksToOpen.map(m => m.type), // inner (opened here) — close first\n            ...activeMarksClosingHere, // outer (were active before) — close last\n          ]\n        } else {\n          marksToCloseAtEnd = findMarksToCloseAtEnd(activeMarks, currentMarks, nextNode, this.markSetsEqual.bind(this))\n        }\n\n        // Extract trailing whitespace before closing marks to prevent invalid markdown like \"**text **\"\n        let trailingWhitespace = ''\n        if (marksToCloseAtEnd.length > 0) {\n          const trailingMatch = textContent.match(/(\\s+)$/)\n          if (trailingMatch) {\n            trailingWhitespace = trailingMatch[1]\n            textContent = textContent.slice(0, -trailingWhitespace.length)\n          }\n        }\n\n        marksToCloseAtEnd.forEach(markType => {\n          const mark = activeMarks.get(markType) ?? currentMarks.get(markType)\n          const closeMarkdown = this.getMarkClosing(markType, mark, markOpeningModes.get(markType))\n          if (closeMarkdown) {\n            textContent += closeMarkdown\n          }\n          activeMarks.delete(markType)\n          markOpeningModes.delete(markType)\n        })\n\n        // Add trailing whitespace after the mark closing\n        textContent += trailingWhitespace\n        textContent += middleTrailingWhitespace\n\n        result.push(textContent)\n      } else {\n        // For non-text nodes, close all active marks before rendering, then reopen after\n        const marksToReopen = new Map(activeMarks)\n        const openingModesToReopen = new Map(markOpeningModes)\n\n        // Close all marks before the node\n        const beforeMarkdown = closeMarksBeforeNode(activeMarks, (markType, mark) => {\n          return this.getMarkClosing(markType, mark, markOpeningModes.get(markType))\n        })\n        markOpeningModes.clear()\n\n        // Render the node\n        const nodeContent = this.renderNodeToMarkdown(node, parentNode, i, level)\n\n        // Reopen marks after the node, but NOT after a hard break\n        // Hard breaks should terminate marks (they create a line break where marks don't continue)\n        const afterMarkdown =\n          node.type === 'hardBreak'\n            ? ''\n            : reopenMarksAfterNode(marksToReopen, activeMarks, (markType, mark) => {\n                const openingMode = openingModesToReopen.get(markType) ?? 'markdown'\n                markOpeningModes.set(markType, openingMode)\n                return this.getMarkOpening(markType, mark, openingMode)\n              })\n\n        result.push(beforeMarkdown + nodeContent + afterMarkdown)\n      }\n    })\n\n    return result.join(separator)\n  }\n\n  /**\n   * Get the opening markdown syntax for a mark type.\n   */\n  private getMarkOpening(markType: string, mark: any, openingMode: 'markdown' | 'html' = 'markdown'): string {\n    if (openingMode === 'html') {\n      return this.getHtmlReopenTags(markType)?.open || ''\n    }\n\n    const handlers = this.getHandlersForNodeType(markType)\n    const handler = handlers.length > 0 ? handlers[0] : undefined\n    if (!handler || !handler.renderMarkdown) {\n      return ''\n    }\n\n    // Use a unique placeholder that's extremely unlikely to appear in real content\n    const placeholder = '\\uE000__TIPTAP_MARKDOWN_PLACEHOLDER__\\uE001'\n\n    // For most marks, we can extract the opening syntax by rendering a simple case\n    const syntheticNode: JSONContent = {\n      type: markType,\n      attrs: mark.attrs || {},\n      content: [{ type: 'text', text: placeholder }],\n    }\n\n    try {\n      const rendered = handler.renderMarkdown(\n        syntheticNode,\n        {\n          renderChildren: () => placeholder,\n          renderChild: () => placeholder,\n          indent: (content: string) => content,\n          wrapInBlock: (prefix: string, content: string) => prefix + content,\n        },\n        { index: 0, level: 0, parentType: 'text', meta: {} },\n      )\n\n      // Extract the opening part (everything before placeholder)\n      const placeholderIndex = rendered.indexOf(placeholder)\n      return placeholderIndex >= 0 ? rendered.substring(0, placeholderIndex) : ''\n    } catch (err) {\n      throw new Error(`Failed to get mark opening for ${markType}: ${err}`)\n    }\n  }\n\n  /**\n   * Get the closing markdown syntax for a mark type.\n   */\n  private getMarkClosing(markType: string, mark: any, openingMode: 'markdown' | 'html' = 'markdown'): string {\n    if (openingMode === 'html') {\n      return this.getHtmlReopenTags(markType)?.close || ''\n    }\n\n    const handlers = this.getHandlersForNodeType(markType)\n    const handler = handlers.length > 0 ? handlers[0] : undefined\n    if (!handler || !handler.renderMarkdown) {\n      return ''\n    }\n\n    // Use a unique placeholder that's extremely unlikely to appear in real content\n    const placeholder = '\\uE000__TIPTAP_MARKDOWN_PLACEHOLDER__\\uE001'\n\n    const syntheticNode: JSONContent = {\n      type: markType,\n      attrs: mark.attrs || {},\n      content: [{ type: 'text', text: placeholder }],\n    }\n\n    try {\n      const rendered = handler.renderMarkdown(\n        syntheticNode,\n        {\n          renderChildren: () => placeholder,\n          renderChild: () => placeholder,\n          indent: (content: string) => content,\n          wrapInBlock: (prefix: string, content: string) => prefix + content,\n        },\n        { index: 0, level: 0, parentType: 'text', meta: {} },\n      )\n\n      // Extract the closing part (everything after placeholder)\n      const placeholderIndex = rendered.indexOf(placeholder)\n      const placeholderEnd = placeholderIndex + placeholder.length\n      return placeholderIndex >= 0 ? rendered.substring(placeholderEnd) : ''\n    } catch (err) {\n      throw new Error(`Failed to get mark closing for ${markType}: ${err}`)\n    }\n  }\n\n  /**\n   * Returns the inline HTML tags an extension exposes for overlap-boundary\n   * reopen handling, if that mark explicitly opted into HTML reopen mode.\n   */\n  private getHtmlReopenTags(markType: string): { open: string; close: string } | undefined {\n    const handlers = this.getHandlersForNodeType(markType)\n    const handler = handlers.length > 0 ? handlers[0] : undefined\n\n    return handler?.htmlReopen\n  }\n\n  /**\n   * Check if two mark sets are equal.\n   */\n  private markSetsEqual(marks1: Map<string, any>, marks2: Map<string, any>): boolean {\n    if (marks1.size !== marks2.size) {\n      return false\n    }\n\n    return Array.from(marks1.keys()).every(type => marks2.has(type))\n  }\n}\n\nexport default MarkdownManager\n","import type { Content, MarkdownToken } from '@tiptap/core'\nimport type { Fragment, Node } from '@tiptap/pm/model'\n\nimport type { ContentType } from './types.js'\n\n/**\n * Wraps each line of the content with the given prefix.\n * @param prefix The prefix to wrap each line with.\n * @param content The content to wrap.\n * @returns The content with each line wrapped with the prefix.\n */\nexport function wrapInMarkdownBlock(prefix: string, content: string) {\n  // split content lines\n  const lines = content.split('\\n')\n\n  // add empty strings between every line\n  const output = lines\n    // add empty lines between each block\n    .flatMap(line => [line, ''])\n    // add the prefix to each line\n    .map(line => `${prefix}${line}`)\n    .join('\\n')\n\n  return output.slice(0, output.length - 1)\n}\n\n/**\n * Identifies marks that need to be closed, based on the marks in the next node.\n */\nexport function findMarksToClose(currentMarks: Map<string, any>, nextNode: any): string[] {\n  const marksToClose: string[] = []\n\n  Array.from(currentMarks.keys()).forEach(markType => {\n    if (!nextNode || !nextNode.marks || !nextNode.marks.map((mark: any) => mark.type).includes(markType)) {\n      marksToClose.push(markType)\n    }\n  })\n  return marksToClose\n}\n\n/**\n * Identifies marks that need to be opened (in current node but not active).\n */\nexport function findMarksToOpen(\n  activeMarks: Map<string, any>,\n  currentMarks: Map<string, any>,\n): Array<{ type: string; mark: any }> {\n  const marksToOpen: Array<{ type: string; mark: any }> = []\n  Array.from(currentMarks.entries()).forEach(([markType, mark]) => {\n    if (!activeMarks.has(markType)) {\n      marksToOpen.push({ type: markType, mark })\n    }\n  })\n  return marksToOpen\n}\n\n/**\n * Determines which marks need to be closed at the end of the current text node.\n * This handles cases where marks end at node boundaries or when transitioning\n * to nodes with different mark sets.\n */\nexport function findMarksToCloseAtEnd(\n  activeMarks: Map<string, any>,\n  currentMarks: Map<string, any>,\n  nextNode: any,\n  markSetsEqual: (a: Map<string, any>, b: Map<string, any>) => boolean,\n): string[] {\n  const isLastNode = !nextNode\n  const nextNodeHasNoMarks = nextNode && nextNode.type === 'text' && (!nextNode.marks || nextNode.marks.length === 0)\n  const nextNodeHasDifferentMarks =\n    nextNode &&\n    nextNode.type === 'text' &&\n    nextNode.marks &&\n    !markSetsEqual(currentMarks, new Map(nextNode.marks.map((mark: any) => [mark.type, mark])))\n\n  const marksToCloseAtEnd: string[] = []\n  if (isLastNode || nextNodeHasNoMarks || nextNodeHasDifferentMarks) {\n    if (nextNode && nextNode.type === 'text' && nextNode.marks) {\n      const nextMarks = new Map(nextNode.marks.map((mark: any) => [mark.type, mark]))\n      Array.from(activeMarks.keys())\n        .reverse()\n        .forEach(markType => {\n          if (!nextMarks.has(markType)) {\n            marksToCloseAtEnd.push(markType)\n          }\n        })\n    } else if (isLastNode || nextNodeHasNoMarks) {\n      // Close all active marks\n      marksToCloseAtEnd.push(...Array.from(activeMarks.keys()).reverse())\n    }\n  }\n\n  return marksToCloseAtEnd\n}\n\n/**\n * Closes active marks before rendering a non-text node.\n * Returns the closing markdown syntax and clears the active marks.\n */\nexport function closeMarksBeforeNode(\n  activeMarks: Map<string, any>,\n  getMarkClosing: (markType: string, mark: any) => string,\n): string {\n  let beforeMarkdown = ''\n  Array.from(activeMarks.keys())\n    .reverse()\n    .forEach(markType => {\n      const mark = activeMarks.get(markType)\n      const closeMarkdown = getMarkClosing(markType, mark)\n      if (closeMarkdown) {\n        beforeMarkdown = closeMarkdown + beforeMarkdown\n      }\n    })\n  activeMarks.clear()\n  return beforeMarkdown\n}\n\n/**\n * Reopens marks after rendering a non-text node.\n * Returns the opening markdown syntax and updates the active marks.\n */\nexport function reopenMarksAfterNode(\n  marksToReopen: Map<string, any>,\n  activeMarks: Map<string, any>,\n  getMarkOpening: (markType: string, mark: any) => string,\n): string {\n  let afterMarkdown = ''\n  Array.from(marksToReopen.entries()).forEach(([markType, mark]) => {\n    const openMarkdown = getMarkOpening(markType, mark)\n    if (openMarkdown) {\n      afterMarkdown += openMarkdown\n    }\n    activeMarks.set(markType, mark)\n  })\n  return afterMarkdown\n}\n\n/**\n * Check if a markdown list item token is a task item and extract its state.\n *\n * @param item The list item token to check\n * @returns Object containing isTask flag, checked state, and indentation level\n *\n * @example\n * ```ts\n * isTaskItem({ raw: '- [ ] Task' }) // { isTask: true, checked: false, indentLevel: 0 }\n * isTaskItem({ raw: '  - [x] Done' }) // { isTask: true, checked: true, indentLevel: 2 }\n * isTaskItem({ raw: '- Regular' }) // { isTask: false, indentLevel: 0 }\n * ```\n */\nexport function isTaskItem(item: MarkdownToken): { isTask: boolean; 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{\n  type InsertContentAtOptions as MarkdownInsertContentAtOptions,\n  type InsertContentOptions as MarkdownInsertContentOptions,\n  type SetContentOptions as MarkdownSetContentOptions,\n  commands,\n  Extension,\n} from '@tiptap/core'\nimport type { marked } from 'marked'\n\nimport MarkdownManager from './MarkdownManager.js'\nimport type { ContentType } from './types.js'\nimport { assumeContentType } from './utils.js'\n\ndeclare module '@tiptap/core' {\n  interface Editor {\n    /**\n     * Get the content of the editor as markdown.\n     */\n    getMarkdown: () => string\n\n    /**\n     * The markdown manager instance.\n     */\n    markdown?: MarkdownManager\n  }\n\n  interface EditorOptions {\n    /**\n     * The content type the content is provided as.\n     *\n     * @default 'json'\n     */\n    contentType?: ContentType\n  }\n\n  interface Storage {\n    markdown: MarkdownExtensionStorage\n  }\n\n  interface InsertContentOptions {\n    /**\n     * The content type the content is provided as.\n     *\n     * @default 'json'\n     */\n    contentType?: ContentType\n  }\n\n  interface InsertContentAtOptions {\n    /**\n     * The content type the content is provided as.\n     *\n     * @default 'json'\n     */\n    contentType?: ContentType\n  }\n\n  interface SetContentOptions {\n    /**\n     * The content type the content is provided as.\n     *\n     * @default 'json'\n     */\n    contentType?: ContentType\n  }\n}\n\nexport type MarkdownExtensionOptions = {\n  /**\n   * Configure the indentation style and size for lists and code blocks.\n   * - `style`: Choose between spaces or tabs. Default is 'space'.\n   * - `size`: Number of spaces or tabs for indentation. Default is 2.\n   */\n  indentation?: { style?: 'space' | 'tab'; size?: number }\n\n  /**\n   * Use a custom version of `marked` for markdown parsing and serialization.\n   * If not provided, the default `marked` instance will be used.\n   */\n  marked?: typeof marked\n\n  /**\n   * Options to pass to `marked.setOptions()`.\n   * See the [marked documentation](https://marked.js.org/using_advanced#options) for available options.\n   */\n  markedOptions?: Parameters<typeof marked.setOptions>[0]\n}\n\nexport type MarkdownExtensionStorage = {\n  manager: MarkdownManager\n}\n\nexport const Markdown = Extension.create<MarkdownExtensionOptions, MarkdownExtensionStorage>({\n  name: 'markdown',\n\n  addOptions() {\n    return {\n      indentation: { style: 'space', size: 2 },\n      marked: undefined,\n      markedOptions: {},\n    }\n  },\n\n  addCommands() {\n    return {\n      setContent: (content, options?: MarkdownSetContentOptions) => {\n        // if no contentType is specified, we assume the content is in JSON format OR HTML format\n        if (!options?.contentType) {\n          return commands.setContent(content, options)\n        }\n\n        const actualContentType = assumeContentType(content, options?.contentType)\n\n        if (actualContentType !== 'markdown' || !this.editor.markdown) {\n          return commands.setContent(content, options)\n        }\n\n        const mdContent = this.editor.markdown.parse(content as string)\n        return commands.setContent(mdContent, options)\n      },\n\n      insertContent: (value, options?: MarkdownInsertContentOptions) => {\n        // if no contentType is specified, we assume the content is in JSON format OR HTML format\n        if (!options?.contentType) {\n          return commands.insertContent(value, options)\n        }\n\n        const actualContentType = assumeContentType(value, options?.contentType)\n\n        if (actualContentType !== 'markdown' || !this.editor.markdown) {\n          return commands.insertContent(value, options)\n        }\n\n        const mdContent = this.editor.markdown.parse(value as string)\n        return commands.insertContent(mdContent, options)\n      },\n\n      insertContentAt: (position, value, options?: MarkdownInsertContentAtOptions) => {\n        // if no contentType is specified, we assume the content is in JSON format OR HTML format\n        if (!options?.contentType) {\n          return commands.insertContentAt(position, value, options)\n        }\n\n        const actualContentType = assumeContentType(value, options?.contentType)\n\n        if (actualContentType !== 'markdown' || !this.editor.markdown) {\n          return commands.insertContentAt(position, value, options)\n        }\n\n        const mdContent = this.editor.markdown.parse(value as string)\n        return commands.insertContentAt(position, mdContent, options)\n      },\n    }\n  },\n\n  addStorage() {\n    return {\n      manager: new MarkdownManager({\n        indentation: this.options.indentation,\n        marked: this.options.marked,\n        markedOptions: this.options.markedOptions,\n        extensions: [],\n      }),\n    }\n  },\n\n  onBeforeCreate() {\n    if (this.editor.markdown) {\n      console.error(\n        '[tiptap][markdown]: There is already a `markdown` property on the editor instance. This might lead to unexpected behavior.',\n      )\n      return\n    }\n\n    this.storage.manager = new MarkdownManager({\n      indentation: this.options.indentation,\n      marked: this.options.marked,\n      markedOptions: this.options.markedOptions,\n      extensions: this.editor.extensionManager.baseExtensions,\n    })\n\n    this.editor.markdown = this.storage.manager\n\n    // add a `getMarkdown()` method to the editor\n    this.editor.getMarkdown = () => {\n      return this.storage.manager.serialize(this.editor.getJSON())\n    }\n\n    if (!this.editor.options.contentType) {\n      return\n    }\n\n    const assumedType = assumeContentType(this.editor.options.content, this.editor.options.contentType)\n    if (assumedType !== 'markdown') {\n      return\n    }\n\n    if (!this.editor.markdown) {\n      throw new Error(\n        '[tiptap][markdown]: The `contentType` option is set to \"markdown\", but the Markdown extension is not added to the editor. Please add the Markdown extension to use this feature.',\n      )\n    }\n\n    if (this.editor.options.content === undefined || typeof this.editor.options.content !== 'string') {\n      throw new Error(\n        '[tiptap][markdown]: The `contentType` option is set to \"markdown\", but the initial content is not a string. Please provide the initial content as a markdown string.',\n      )\n    }\n\n    const json = this.editor.markdown.parse(this.editor.options.content as string)\n    this.editor.options.content = json\n  },\n})\n","import {\n  type AnyExtension,\n  type ExtendableConfig,\n  type JSONContent,\n  type MarkdownExtensionSpec,\n  type MarkdownLexerConfiguration,\n  type MarkdownParseHelpers,\n  type MarkdownParseResult,\n  type MarkdownRendererHelpers,\n  type MarkdownToken,\n  type MarkdownTokenizer,\n  type RenderContext,\n  flattenExtensions,\n  generateJSON,\n  getExtensionField,\n} from '@tiptap/core'\nimport { type Lexer, type Token, type TokenizerExtension, type TokenizerThis, marked } from 'marked'\n\nimport {\n  closeMarksBeforeNode,\n  findMarksToClose,\n  findMarksToCloseAtEnd,\n  findMarksToOpen,\n  isTaskItem,\n  reopenMarksAfterNode,\n  wrapInMarkdownBlock,\n} from './utils.js'\n\nexport class MarkdownManager {\n  private markedInstance: typeof marked\n  private activeParseLexer: Lexer | null = null\n  private registry: Map<string, MarkdownExtensionSpec[]>\n  private nodeTypeRegistry: Map<string, MarkdownExtensionSpec[]>\n  private indentStyle: 'space' | 'tab'\n  private indentSize: number\n  private baseExtensions: AnyExtension[] = []\n  private extensions: AnyExtension[] = []\n\n  /**\n   * Create a MarkdownManager.\n   * @param options.marked Optional marked instance to use (injected).\n   * @param options.markedOptions Optional options to pass to marked.setOptions\n   * @param options.indentation Indentation settings (style and size).\n   * @param options.extensions An array of Tiptap extensions to register for markdown parsing and rendering.\n   */\n  constructor(options?: {\n    marked?: typeof marked\n    markedOptions?: Parameters<typeof marked.setOptions>[0]\n    indentation?: { style?: 'space' | 'tab'; size?: number }\n    extensions: AnyExtension[]\n  }) {\n    this.markedInstance = options?.marked ?? marked\n    this.indentStyle = options?.indentation?.style ?? 'space'\n    this.indentSize = options?.indentation?.size ?? 2\n    this.baseExtensions = options?.extensions || []\n\n    if (options?.markedOptions && typeof this.markedInstance.setOptions === 'function') {\n      this.markedInstance.setOptions(options.markedOptions)\n    }\n\n    this.registry = new Map()\n    this.nodeTypeRegistry = new Map()\n\n    // If extensions were provided, register them now\n    if (options?.extensions) {\n      this.baseExtensions = options.extensions\n      const flattened = flattenExtensions(options.extensions)\n      flattened.forEach(ext => this.registerExtension(ext))\n    }\n  }\n\n  /** Returns the underlying marked instance. */\n  get instance(): typeof marked {\n    return this.markedInstance\n  }\n\n  /** Returns the correct indentCharacter (space or tab) */\n  get indentCharacter(): string {\n    return this.indentStyle === 'space' ? ' ' : '\\t'\n  }\n\n  /** Returns the correct indentString repeated X times */\n  get indentString(): string {\n    return this.indentCharacter.repeat(this.indentSize)\n  }\n\n  /** Helper to quickly check whether a marked instance is available. */\n  hasMarked(): boolean {\n    return !!this.markedInstance\n  }\n\n  /**\n   * Register a Tiptap extension (Node/Mark/Extension). This will read\n   * `markdownName`, `parseMarkdown`, `renderMarkdown` and `priority` from the\n   * extension config (using the same resolution used across the codebase).\n   */\n  registerExtension(extension: AnyExtension): void {\n    // Keep track of all extensions for HTML parsing\n    this.extensions.push(extension)\n\n    const name = extension.name\n    const tokenName =\n      (getExtensionField(extension, 'markdownTokenName') as ExtendableConfig['markdownTokenName']) || name\n    const parseMarkdown = getExtensionField(extension, 'parseMarkdown') as ExtendableConfig['parseMarkdown'] | undefined\n    const renderMarkdown = getExtensionField(extension, 'renderMarkdown') as\n      | ExtendableConfig['renderMarkdown']\n      | undefined\n    const tokenizer = getExtensionField(extension, 'markdownTokenizer') as\n      | ExtendableConfig['markdownTokenizer']\n      | undefined\n\n    // Read the `markdown` object from the extension config. This allows\n    // extensions to provide `markdown: { name?, parseName?, renderName?, parse?, render?, match? }`.\n    const markdownCfg = (getExtensionField(extension, 'markdownOptions') ?? null) as ExtendableConfig['markdownOptions']\n    const isIndenting = markdownCfg?.indentsContent ?? false\n    const htmlReopen = markdownCfg?.htmlReopen\n\n    const spec: MarkdownExtensionSpec = {\n      tokenName,\n      nodeName: name,\n      parseMarkdown,\n      renderMarkdown,\n      isIndenting,\n      htmlReopen,\n      tokenizer,\n    }\n\n    // Add to parse registry using parseName\n    if (tokenName && parseMarkdown) {\n      const parseExisting = this.registry.get(tokenName) || []\n      parseExisting.push(spec)\n      this.registry.set(tokenName, parseExisting)\n    }\n\n    // Add to render registry using renderName (node type)\n    if (renderMarkdown) {\n      const renderExisting = this.nodeTypeRegistry.get(name) || []\n      renderExisting.push(spec)\n      this.nodeTypeRegistry.set(name, renderExisting)\n    }\n\n    // Register custom tokenizer with marked.js\n    if (tokenizer && this.hasMarked()) {\n      this.registerTokenizer(tokenizer)\n    }\n  }\n\n  private createLexer(): Lexer {\n    return new this.markedInstance.Lexer()\n  }\n\n  private createTokenizerHelpers(lexer: Lexer): MarkdownLexerConfiguration {\n    return {\n      inlineTokens: (src: string) => lexer.inlineTokens(src),\n      blockTokens: (src: string) => lexer.blockTokens(src),\n    }\n  }\n\n  private tokenizeInline(src: string): MarkdownToken[] {\n    return (this.activeParseLexer ?? this.createLexer()).inlineTokens(src) as MarkdownToken[]\n  }\n\n  /**\n   * Register a custom tokenizer with marked.js for parsing non-standard markdown syntax.\n   */\n  private registerTokenizer(tokenizer: MarkdownTokenizer): void {\n    if (!this.hasMarked()) {\n      return\n    }\n\n    const { name, start, level = 'inline', tokenize } = tokenizer\n    const createTokenizerHelpers = this.createTokenizerHelpers.bind(this)\n    const createLexer = this.createLexer.bind(this)\n\n    let startCb: (src: string) => number\n\n    if (!start) {\n      startCb = (src: string) => {\n        // For other tokenizers, try to find a match and return its position\n        const result = tokenize(src, [], this.createTokenizerHelpers(this.createLexer()))\n        if (result && result.raw) {\n          const index = src.indexOf(result.raw)\n          return index\n        }\n        return -1\n      }\n    } else {\n      startCb = typeof start === 'function' ? start : (src: string) => src.indexOf(start)\n    }\n\n    // Create marked.js extension with proper types\n    const markedExtension: TokenizerExtension = {\n      name,\n      level,\n      start: startCb,\n      tokenizer(this: TokenizerThis, src, tokens) {\n        const helper = this.lexer ? createTokenizerHelpers(this.lexer) : createTokenizerHelpers(createLexer())\n        const result = tokenize(src, tokens, helper)\n\n        if (result && result.type) {\n          return {\n            ...result,\n            type: result.type || name,\n            raw: result.raw || '',\n            tokens: (result.tokens || []) as Token[],\n          }\n        }\n\n        return undefined\n      },\n      childTokens: [],\n    }\n\n    // Register with marked.js - use extensions array to control priority\n    this.markedInstance.use({\n      extensions: [markedExtension],\n    })\n  }\n\n  /** Get registered handlers for a token type and try each until one succeeds. */\n  private getHandlersForToken(type: string): MarkdownExtensionSpec[] {\n    try {\n      return this.registry.get(type) || []\n    } catch {\n      return []\n    }\n  }\n\n  /** Get the first handler for a token type (for backwards compatibility). */\n  private getHandlerForToken(type: string): MarkdownExtensionSpec | undefined {\n    // First try the markdown token registry (for parsing)\n    const markdownHandlers = this.getHandlersForToken(type)\n    if (markdownHandlers.length > 0) {\n      return markdownHandlers[0]\n    }\n\n    // Then try the node type registry (for rendering)\n    const nodeTypeHandlers = this.getHandlersForNodeType(type)\n    return nodeTypeHandlers.length > 0 ? nodeTypeHandlers[0] : undefined\n  }\n\n  /** Get registered handlers for a node type (for rendering). */\n  private getHandlersForNodeType(type: string): MarkdownExtensionSpec[] {\n    try {\n      return this.nodeTypeRegistry.get(type) || []\n    } catch {\n      return []\n    }\n  }\n\n  /**\n   * Serialize a ProseMirror-like JSON document (or node array) to a Markdown string\n   * using registered renderers and fallback renderers.\n   */\n  serialize(docOrContent: JSONContent): string {\n    if (!docOrContent) {\n      return ''\n    }\n\n    const result = this.renderNodes(docOrContent, docOrContent)\n    // Return empty string if result is only whitespace entities or non-breaking spaces\n    return this.isEmptyOutput(result) ? '' : result\n  }\n\n  /**\n   * Check if the markdown output represents an empty document.\n   * Empty documents may contain only &nbsp; entities or non-breaking space characters\n   * which are used by the Paragraph extension to preserve blank lines.\n   */\n  private isEmptyOutput(markdown: string): boolean {\n    if (!markdown || markdown.trim() === '') {\n      return true\n    }\n\n    // Check if the output is only &nbsp; entities or non-breaking space characters\n    const cleanedOutput = markdown\n      .replace(/&nbsp;/g, '')\n      .replace(/\\u00A0/g, '')\n      .trim()\n    return cleanedOutput === ''\n  }\n\n  /**\n   * Parse markdown string into Tiptap JSON document using registered extension handlers.\n   */\n  parse(markdown: string): JSONContent {\n    if (!this.hasMarked()) {\n      throw new Error('No marked instance available for parsing')\n    }\n\n    const previousParseLexer = this.activeParseLexer\n    const parseLexer = this.createLexer()\n\n    this.activeParseLexer = parseLexer\n\n    try {\n      // Use a parse-scoped lexer so follow-up inline tokenization can reuse\n      // the same configured lexer state without sharing it across parses.\n      const tokens = parseLexer.lex(markdown) as MarkdownToken[]\n\n      // Convert tokens to Tiptap JSON\n      const content = this.parseTokens(tokens, true)\n\n      // Return a document node containing the parsed content\n      return {\n        type: 'doc',\n        content,\n      }\n    } finally {\n      this.activeParseLexer = previousParseLexer\n    }\n  }\n\n  /**\n   * Convert an array of marked tokens into Tiptap JSON nodes using registered extension handlers.\n   */\n  private parseTokens(tokens: MarkdownToken[], parseImplicitEmptyParagraphs = false): JSONContent[] {\n    const nonSpaceTokenIndexes = tokens.reduce<number[]>((indexes, token, index) => {\n      if (token.type !== 'space') {\n        indexes.push(index)\n      }\n\n      return indexes\n    }, [])\n\n    let previousNonSpaceTokenIndex = -1\n    let nextNonSpaceTokenPointer = 0\n\n    return tokens.flatMap((token, index) => {\n      while (\n        nextNonSpaceTokenPointer < nonSpaceTokenIndexes.length &&\n        nonSpaceTokenIndexes[nextNonSpaceTokenPointer] < index\n      ) {\n        previousNonSpaceTokenIndex = nonSpaceTokenIndexes[nextNonSpaceTokenPointer]\n        nextNonSpaceTokenPointer += 1\n      }\n\n      if (parseImplicitEmptyParagraphs && token.type === 'space') {\n        const nextNonSpaceTokenIndex = nonSpaceTokenIndexes[nextNonSpaceTokenPointer] ?? -1\n\n        return this.createImplicitEmptyParagraphsFromSpace(token, previousNonSpaceTokenIndex, nextNonSpaceTokenIndex)\n      }\n\n      const parsed = this.parseToken(token, parseImplicitEmptyParagraphs)\n\n      if (parsed === null) {\n        return []\n      }\n\n      return Array.isArray(parsed) ? parsed : [parsed]\n    })\n  }\n\n  private createImplicitEmptyParagraphsFromSpace(\n    token: MarkdownToken,\n    previousNonSpaceTokenIndex: number,\n    nextNonSpaceTokenIndex: number,\n  ): JSONContent[] {\n    const separatorCount = this.countParagraphSeparators(token.raw || '')\n\n    if (separatorCount === 0) {\n      return []\n    }\n\n    const isBoundarySpace = previousNonSpaceTokenIndex === -1 || nextNonSpaceTokenIndex === -1\n    const emptyParagraphCount = Math.max(separatorCount - (isBoundarySpace ? 0 : 1), 0)\n\n    return Array.from({ length: emptyParagraphCount }, () => ({ type: 'paragraph', content: [] }))\n  }\n\n  private countParagraphSeparators(raw: string): number {\n    return (raw.replace(/\\r\\n/g, '\\n').match(/\\n\\n/g) || []).length\n  }\n\n  /**\n   * Parse a single token into Tiptap JSON using the appropriate registered handler.\n   */\n  private parseToken(token: MarkdownToken, parseImplicitEmptyParagraphs = false): JSONContent | JSONContent[] | null {\n    if (!token.type) {\n      return null\n    }\n\n    // Special handling for 'list' tokens that may contain mixed bullet/task items\n    if (token.type === 'list') {\n      return this.parseListToken(token)\n    }\n\n    const handlers = this.getHandlersForToken(token.type)\n    const helpers = this.createParseHelpers()\n\n    // Try each handler until one returns a valid result\n    const result = handlers.find(handler => {\n      if (!handler.parseMarkdown) {\n        return false\n      }\n\n      const parseResult = handler.parseMarkdown(token, helpers)\n      const normalized = this.normalizeParseResult(parseResult)\n\n      // Check if this handler returned a valid result (not null/empty array)\n      if (normalized && (!Array.isArray(normalized) || normalized.length > 0)) {\n        // Store result for return\n        this.lastParseResult = normalized\n        return true\n      }\n\n      return false\n    })\n\n    // If a handler worked, return its result\n    if (result && this.lastParseResult) {\n      const toReturn = this.lastParseResult\n      this.lastParseResult = null // Clean up\n      return toReturn\n    }\n\n    // If no handler worked, try fallback parsing\n    return this.parseFallbackToken(token, parseImplicitEmptyParagraphs)\n  }\n\n  private lastParseResult: JSONContent | JSONContent[] | null = null\n\n  /**\n   * Parse a list token, handling mixed bullet and task list items by splitting them into separate lists.\n   * This ensures that consecutive task items and bullet items are grouped and parsed as separate list nodes.\n   *\n   * @param token The list token to parse\n   * @returns Array of parsed list nodes, or null if parsing fails\n   */\n  private parseListToken(token: MarkdownToken): JSONContent | JSONContent[] | null {\n    if (!token.items || token.items.length === 0) {\n      // No items, parse normally\n      return this.parseTokenWithHandlers(token)\n    }\n\n    const hasTask = token.items.some(item => isTaskItem(item).isTask)\n    const hasNonTask = token.items.some(item => !isTaskItem(item).isTask)\n\n    if (!hasTask || !hasNonTask || this.getHandlersForToken('taskList').length === 0) {\n      // Not mixed or no taskList extension, parse normally\n      return this.parseTokenWithHandlers(token)\n    }\n\n    // Mixed list with taskList extension available: split into separate lists\n    type TaskListItemToken = MarkdownToken & { type: 'taskItem'; checked?: boolean; indentLevel?: number }\n    const groups: { type: 'list' | 'taskList'; items: (MarkdownToken | TaskListItemToken)[] }[] = []\n    let currentGroup: (MarkdownToken | TaskListItemToken)[] = []\n    let currentType: 'list' | 'taskList' | null = null\n\n    for (let i = 0; i < token.items.length; i += 1) {\n      const item = token.items[i]\n      const { isTask, checked, indentLevel } = isTaskItem(item)\n      let processedItem = item\n\n      if (isTask) {\n        // Transform list_item into taskItem token\n        const raw = item.raw || item.text || ''\n\n        // Split raw content by lines to separate main content from nested\n        const lines = raw.split('\\n')\n\n        // Extract main content from the first line\n        const firstLineMatch = lines[0].match(/^\\s*[-+*]\\s+\\[([ xX])\\]\\s+(.*)$/)\n        const mainContent = firstLineMatch ? firstLineMatch[2] : ''\n\n        // Parse nested content from remaining lines\n        let nestedTokens: MarkdownToken[] = []\n        if (lines.length > 1) {\n          // Join all lines after the first\n          const nestedRaw = lines.slice(1).join('\\n')\n\n          // Only parse if there's actual content\n          if (nestedRaw.trim()) {\n            // Find minimum indentation of non-empty lines\n            const nestedLines = lines.slice(1)\n            const nonEmptyLines = nestedLines.filter(line => line.trim())\n            if (nonEmptyLines.length > 0) {\n              const minIndent = Math.min(...nonEmptyLines.map(line => line.length - line.trimStart().length))\n              // Remove common indentation while preserving structure\n              const trimmedLines = nestedLines.map(line => {\n                if (!line.trim()) {\n                  return '' // Keep empty lines\n                }\n                return line.slice(minIndent)\n              })\n              const nestedContent = trimmedLines.join('\\n').trim()\n              // Use the lexer to parse nested content\n              if (nestedContent) {\n                // Use the full lexer pipeline to ensure inline tokens are populated\n                nestedTokens = this.markedInstance.lexer(`${nestedContent}\\n`)\n              }\n            }\n          }\n        }\n\n        processedItem = {\n          type: 'taskItem',\n          raw: '',\n          mainContent,\n          indentLevel,\n          checked: checked ?? false,\n          text: mainContent,\n          tokens: this.tokenizeInline(mainContent),\n          nestedTokens,\n        }\n      }\n\n      const itemType: 'list' | 'taskList' = isTask ? 'taskList' : 'list'\n\n      if (currentType !== itemType) {\n        if (currentGroup.length > 0) {\n          groups.push({ type: currentType!, items: currentGroup })\n        }\n        currentGroup = [processedItem]\n        currentType = itemType\n      } else {\n        currentGroup.push(processedItem)\n      }\n    }\n\n    if (currentGroup.length > 0) {\n      groups.push({ type: currentType!, items: currentGroup })\n    }\n\n    // Parse each group as a separate token\n    const results: JSONContent[] = []\n    for (let i = 0; i < groups.length; i += 1) {\n      const group = groups[i]\n      const subToken = { ...token, type: group.type, items: group.items }\n      const parsed = this.parseToken(subToken)\n      if (parsed) {\n        if (Array.isArray(parsed)) {\n          results.push(...parsed)\n        } else {\n          results.push(parsed)\n        }\n      }\n    }\n\n    return results.length > 0 ? results : null\n  }\n\n  /**\n   * Parse a token using registered handlers (extracted for reuse).\n   */\n  private parseTokenWithHandlers(token: MarkdownToken): JSONContent | JSONContent[] | null {\n    if (!token.type) {\n      return null\n    }\n\n    const handlers = this.getHandlersForToken(token.type)\n    const helpers = this.createParseHelpers()\n\n    // Try each handler until one returns a valid result\n    const result = handlers.find(handler => {\n      if (!handler.parseMarkdown) {\n        return false\n      }\n\n      const parseResult = handler.parseMarkdown(token, helpers)\n      const normalized = this.normalizeParseResult(parseResult)\n\n      // Check if this handler returned a valid result (not null/empty array)\n      if (normalized && (!Array.isArray(normalized) || normalized.length > 0)) {\n        // Store result for return\n        this.lastParseResult = normalized\n        return true\n      }\n\n      return false\n    })\n\n    // If a handler worked, return its result\n    if (result && this.lastParseResult) {\n      const toReturn = this.lastParseResult\n      this.lastParseResult = null // Clean up\n      return toReturn\n    }\n\n    // If no handler worked, try fallback parsing\n    return this.parseFallbackToken(token)\n  }\n\n  /**\n   * Creates helper functions for parsing markdown tokens.\n   * @returns An object containing helper functions for parsing.\n   */\n  private createParseHelpers(): MarkdownParseHelpers {\n    return {\n      parseInline: (tokens: MarkdownToken[]) => this.parseInlineTokens(tokens),\n      parseChildren: (tokens: MarkdownToken[]) => this.parseTokens(tokens),\n      parseBlockChildren: (tokens: MarkdownToken[]) => this.parseTokens(tokens, true),\n      createTextNode: (text: string, marks?: Array<{ type: string; attrs?: any }>) => {\n        const node = {\n          type: 'text',\n          text,\n          marks: marks || undefined,\n        }\n\n        return node\n      },\n      createNode: (type: string, attrs?: any, content?: JSONContent[]) => {\n        const node = {\n          type,\n          attrs: attrs || undefined,\n          content: content || undefined,\n        }\n\n        if (!attrs || Object.keys(attrs).length === 0) {\n          delete node.attrs\n        }\n\n        return node\n      },\n      applyMark: (markType: string, content: JSONContent[], attrs?: any) => ({\n        mark: markType,\n        content,\n        attrs: attrs && Object.keys(attrs).length > 0 ? attrs : undefined,\n      }),\n    }\n  }\n\n  /**\n   * Escape special regex characters in a string.\n   */\n  private escapeRegex(str: string): string {\n    return str.replace(/[.*+?^${}()|[\\]\\\\]/g, '\\\\$&')\n  }\n\n  /**\n   * Parse inline tokens (bold, italic, links, etc.) into text nodes with marks.\n   * This is the complex part that handles mark nesting and boundaries.\n   */\n  private parseInlineTokens(tokens: MarkdownToken[]): JSONContent[] {\n    const result: JSONContent[] = []\n\n    // Process tokens sequentially using an index so we can lookahead and\n    // merge split inline HTML fragments like: text / <em> / inner / </em> / text\n    for (let i = 0; i < tokens.length; i += 1) {\n      const token = tokens[i]\n\n      if (token.type === 'text') {\n        result.push({\n          type: 'text',\n          text: token.text || '',\n        })\n      } else if (token.type === 'html') {\n        // Handle possible split inline HTML by attempting to detect an\n        // opening tag and searching forward for a matching closing tag.\n        const raw = (token.raw ?? token.text ?? '').toString()\n\n        // Quick checks for opening vs. closing tag\n        const isClosing = /^<\\/[\\s]*[\\w-]+/i.test(raw)\n        const openMatch = raw.match(/^<[\\s]*([\\w-]+)(\\s|>|\\/|$)/i)\n\n        if (!isClosing && openMatch && !/\\/>$/.test(raw)) {\n          // Try to find the corresponding closing html token for this tag\n          const tagName = openMatch[1]\n          const escapedTagName = this.escapeRegex(tagName)\n          const closingRegex = new RegExp(`^<\\\\/\\\\s*${escapedTagName}\\\\b`, 'i')\n          let foundIndex = -1\n\n          // Collect intermediate raw parts to reconstruct full HTML fragment\n          const parts: string[] = [raw]\n          for (let j = i + 1; j < tokens.length; j += 1) {\n            const t = tokens[j]\n            const tRaw = (t.raw ?? t.text ?? '').toString()\n            parts.push(tRaw)\n            if (t.type === 'html' && closingRegex.test(tRaw)) {\n              foundIndex = j\n              break\n            }\n          }\n\n          if (foundIndex !== -1) {\n            // Merge opening + inner + closing into one html fragment and parse\n            const mergedRaw = parts.join('')\n            const mergedToken = {\n              type: 'html',\n              raw: mergedRaw,\n              text: mergedRaw,\n              block: false,\n            } as unknown as MarkdownToken\n\n            const parsed = this.parseHTMLToken(mergedToken)\n            if (parsed) {\n              const normalized = this.normalizeParseResult(parsed as any)\n              if (Array.isArray(normalized)) {\n                result.push(...normalized)\n              } else if (normalized) {\n                result.push(normalized)\n              }\n            }\n\n            // Advance i to the closing token\n            i = foundIndex\n            continue\n          }\n        }\n\n        // Fallback: single html token parse\n        const parsedSingle = this.parseHTMLToken(token)\n        if (parsedSingle) {\n          const normalized = this.normalizeParseResult(parsedSingle as any)\n          if (Array.isArray(normalized)) {\n            result.push(...normalized)\n          } else if (normalized) {\n            result.push(normalized)\n          }\n        }\n      } else if (token.type) {\n        // Handle inline marks (bold, italic, etc.)\n        const markHandler = this.getHandlerForToken(token.type)\n        if (markHandler && markHandler.parseMarkdown) {\n          const helpers = this.createParseHelpers()\n          const parsed = markHandler.parseMarkdown(token, helpers)\n\n          if (this.isMarkResult(parsed)) {\n            // This is a mark result - apply the mark to the content\n            const markedContent = this.applyMarkToContent(parsed.mark, parsed.content, parsed.attrs)\n            result.push(...markedContent)\n          } else {\n            // Regular inline node\n            const normalized = this.normalizeParseResult(parsed)\n            if (Array.isArray(normalized)) {\n              result.push(...normalized)\n            } else if (normalized) {\n              result.push(normalized)\n            }\n          }\n        } else if (token.tokens) {\n          // Fallback: try to parse children if they exist\n          result.push(...this.parseInlineTokens(token.tokens))\n        }\n      }\n    }\n\n    return result\n  }\n\n  /**\n   * Apply a mark to content nodes.\n   */\n  private applyMarkToContent(markType: string, content: JSONContent[], attrs?: any): JSONContent[] {\n    return content.map(node => {\n      if (node.type === 'text') {\n        // Add the mark to existing marks or create new marks array\n        const existingMarks = node.marks || []\n        const newMark = attrs ? { type: markType, attrs } : { type: markType }\n        return {\n          ...node,\n          marks: [...existingMarks, newMark],\n        }\n      }\n\n      // For non-text nodes, recursively apply to content\n      return {\n        ...node,\n        content: node.content ? this.applyMarkToContent(markType, node.content, attrs) : undefined,\n      }\n    })\n  } /**\n   * Check if a parse result represents a mark to be applied.\n   */\n  private isMarkResult(result: any): result is { mark: string; content: JSONContent[]; attrs?: any } {\n    return result && typeof result === 'object' && 'mark' in result\n  }\n\n  /**\n   * Normalize parse results to ensure they're valid JSONContent.\n   */\n  private normalizeParseResult(result: MarkdownParseResult): JSONContent | JSONContent[] | null {\n    if (!result) {\n      return null\n    }\n\n    if (this.isMarkResult(result)) {\n      // This shouldn't happen at the top level, but handle it gracefully\n      return result.content\n    }\n\n    return result as JSONContent | JSONContent[]\n  }\n\n  /**\n   * Fallback parsing for common tokens when no specific handler is registered.\n   */\n  private parseFallbackToken(\n    token: MarkdownToken,\n    parseImplicitEmptyParagraphs = false,\n  ): JSONContent | JSONContent[] | null {\n    switch (token.type) {\n      case 'paragraph':\n        return {\n          type: 'paragraph',\n          content: token.tokens ? this.parseInlineTokens(token.tokens) : [],\n        }\n\n      case 'heading':\n        return {\n          type: 'heading',\n          attrs: { level: token.depth || 1 },\n          content: token.tokens ? this.parseInlineTokens(token.tokens) : [],\n        }\n\n      case 'text':\n        return {\n          type: 'text',\n          text: token.text || '',\n        }\n\n      case 'html':\n        // Parse HTML using extensions' parseHTML methods\n        return this.parseHTMLToken(token)\n\n      case 'space':\n        return null\n\n      default:\n        // Unknown token type - try to parse children if they exist\n        if (token.tokens) {\n          return this.parseTokens(token.tokens, parseImplicitEmptyParagraphs)\n        }\n        return null\n    }\n  }\n\n  /**\n   * Parse HTML tokens using extensions' parseHTML methods.\n   * This allows HTML within markdown to be parsed according to extension rules.\n   */\n  private parseHTMLToken(token: MarkdownToken): JSONContent | JSONContent[] | null {\n    const html = token.text || token.raw || ''\n\n    if (!html.trim()) {\n      return null\n    }\n\n    // Check if we're in a server-side environment (no window object)\n    // If so, fall back to treating HTML as plain text to avoid runtime errors\n    if (typeof window === 'undefined') {\n      // For block-level HTML, wrap in a paragraph to maintain valid document structure\n      if (token.block) {\n        return {\n          type: 'paragraph',\n          content: [\n            {\n              type: 'text',\n              text: html,\n            },\n          ],\n        }\n      }\n      // For inline HTML, return plain text\n      return {\n        type: 'text',\n        text: html,\n      }\n    }\n\n    // Use generateJSON to parse the HTML using extensions' parseHTML rules\n    try {\n      const parsed = generateJSON(html, this.baseExtensions)\n\n      // If the result is a doc node, extract its content\n      if (parsed.type === 'doc' && parsed.content) {\n        // For block-level HTML, return the content array\n        if (token.block) {\n          return parsed.content\n        }\n\n        // For inline HTML, we need to flatten the content appropriately\n        // If there's only one paragraph with content, unwrap it\n        if (parsed.content.length === 1 && parsed.content[0].type === 'paragraph' && parsed.content[0].content) {\n          return parsed.content[0].content\n        }\n\n        return parsed.content\n      }\n\n      return parsed as JSONContent\n    } catch (error) {\n      throw new Error(`Failed to parse HTML in markdown: ${error}`)\n    }\n  }\n\n  renderNodeToMarkdown(\n    node: JSONContent,\n    parentNode?: JSONContent,\n    index = 0,\n    level = 0,\n    meta: Record<string, any> = {},\n  ): string {\n    // if node is a text node, we simply return it's text content\n    // marks are handled at the array level in renderNodesWithMarkBoundaries\n    if (node.type === 'text') {\n      return node.text || ''\n    }\n\n    if (!node.type) {\n      return ''\n    }\n\n    const handler = this.getHandlerForToken(node.type)\n    if (!handler) {\n      return ''\n    }\n\n    const previousNode = Array.isArray(parentNode?.content) && index > 0 ? parentNode.content[index - 1] : undefined\n    const helpers: MarkdownRendererHelpers = {\n      renderChildren: (nodes, separator) => {\n        const childLevel = handler.isIndenting ? level + 1 : level\n\n        if (!Array.isArray(nodes) && (nodes as any).content) {\n          return this.renderNodes((nodes as any).content as JSONContent[], node, separator || '', index, childLevel)\n        }\n\n        return this.renderNodes(nodes, node, separator || '', index, childLevel)\n      },\n      renderChild: (childNode, childIndex) => {\n        const childLevel = handler.isIndenting ? level + 1 : level\n\n        return this.renderNodeToMarkdown(childNode, node, childIndex, childLevel)\n      },\n      indent: content => {\n        return this.indentString + content\n      },\n      wrapInBlock: wrapInMarkdownBlock,\n    }\n\n    const context: RenderContext = {\n      index,\n      level,\n      parentType: parentNode?.type,\n      previousNode,\n      meta: {\n        parentAttrs: parentNode?.attrs,\n        ...meta,\n      },\n    }\n\n    // First render the node itself (this will render children recursively)\n    const rendered = handler.renderMarkdown?.(node, helpers, context) || ''\n\n    return rendered\n  }\n\n  /**\n   * Render a node or an array of nodes. Parent type controls how children\n   * are joined (which determines newline insertion between children).\n   */\n  renderNodes(\n    nodeOrNodes: JSONContent | JSONContent[],\n    parentNode?: JSONContent,\n    separator = '',\n    index = 0,\n    level = 0,\n  ): string {\n    // if we have just one node, call renderNodeToMarkdown directly\n    if (!Array.isArray(nodeOrNodes)) {\n      if (!nodeOrNodes.type) {\n        return ''\n      }\n\n      return this.renderNodeToMarkdown(nodeOrNodes, parentNode, index, level)\n    }\n\n    return this.renderNodesWithMarkBoundaries(nodeOrNodes, parentNode, separator, level)\n  }\n\n  /**\n   * Render an array of nodes while properly tracking mark boundaries.\n   * This handles cases where marks span across multiple text nodes.\n   */\n  private renderNodesWithMarkBoundaries(\n    nodes: JSONContent[],\n    parentNode?: JSONContent,\n    separator = '',\n    level = 0,\n  ): string {\n    const result: string[] = []\n    const activeMarks: Map<string, any> = new Map()\n    const reopenWithHtmlOnNextOpen = new Set<string>()\n    const markOpeningModes = new Map<string, 'markdown' | 'html'>()\n    nodes.forEach((node, i) => {\n      // Lookahead to the next node to determine if marks need to be closed\n      const nextNode = i < nodes.length - 1 ? nodes[i + 1] : null\n\n      if (!node.type) {\n        return\n      }\n\n      if (node.type === 'text') {\n        let textContent = node.text || ''\n        const currentMarks = new Map((node.marks || []).map(mark => [mark.type, mark]))\n\n        // Find marks that need to be closed and opened\n        const marksToOpen = findMarksToOpen(activeMarks, currentMarks)\n        const marksToClose = findMarksToClose(currentMarks, nextNode)\n\n        // When marks simultaneously close (old) AND open (new) at this boundary, the naive\n        // approach of appending old-close and prepending new-open produces interleaved\n        // delimiters like `*456**` (italic open, text, bold close) instead of properly\n        // nested `_456_**` (italic open, text, italic close, bold close).\n        //\n        // The fix: when both are present, defer old mark closings to the end of the node\n        // (after the new marks also close), ensuring correct inner-before-outer order.\n        //\n        // If an already-active mark ends on this node while another mark opens on this same\n        // node, we defer closing the active mark until the end of the node so nesting stays\n        // valid (`**...++abc++**` instead of `**...++abc**++`).\n        const activeMarksClosingHere = marksToClose.filter(markType => activeMarks.has(markType))\n        const hasCrossedBoundary = activeMarksClosingHere.length > 0 && marksToOpen.length > 0\n\n        let middleTrailingWhitespace = ''\n\n        if (marksToClose.length > 0 && !hasCrossedBoundary) {\n          // Extract trailing whitespace before closing marks to prevent invalid markdown like \"**text **\"\n          const middleTrailingMatch = textContent.match(/(\\s+)$/)\n          if (middleTrailingMatch) {\n            middleTrailingWhitespace = middleTrailingMatch[1]\n            textContent = textContent.slice(0, -middleTrailingWhitespace.length)\n          }\n        }\n\n        if (!hasCrossedBoundary) {\n          // Normal path: close marks that are ending here (no new marks opening simultaneously)\n          marksToClose.forEach(markType => {\n            if (!activeMarks.has(markType)) {\n              return\n            }\n\n            const mark = currentMarks.get(markType)\n            const closeMarkdown = this.getMarkClosing(markType, mark, markOpeningModes.get(markType))\n            if (closeMarkdown) {\n              textContent += closeMarkdown\n            }\n            if (activeMarks.has(markType)) {\n              activeMarks.delete(markType)\n              markOpeningModes.delete(markType)\n            }\n          })\n        }\n\n        // Open new marks (should be at the beginning)\n        // Extract leading whitespace before opening marks to prevent invalid markdown like \"** text**\"\n        let leadingWhitespace = ''\n        if (marksToOpen.length > 0) {\n          const leadingMatch = textContent.match(/^(\\s+)/)\n          if (leadingMatch) {\n            leadingWhitespace = leadingMatch[1]\n            textContent = textContent.slice(leadingWhitespace.length)\n          }\n        }\n\n        // Snapshot active mark types before opening new marks, so each new mark's delimiter\n        // is chosen based on what is already active (not including itself).\n        // When crossing a boundary, old marks are still in activeMarks here (not yet removed),\n        // so new marks correctly see them as active context.\n        marksToOpen.forEach(({ type, mark }) => {\n          const openingMode = reopenWithHtmlOnNextOpen.has(type) ? 'html' : 'markdown'\n          const openMarkdown = this.getMarkOpening(type, mark, openingMode)\n          if (openMarkdown) {\n            textContent = openMarkdown + textContent\n          }\n          markOpeningModes.set(type, openingMode)\n          reopenWithHtmlOnNextOpen.delete(type)\n        })\n\n        if (!hasCrossedBoundary) {\n          marksToOpen\n            .slice()\n            .reverse()\n            .forEach(({ type, mark }) => {\n              activeMarks.set(type, mark)\n            })\n        }\n\n        // Add leading whitespace before the mark opening\n        textContent = leadingWhitespace + textContent\n\n        // Determine marks to close at the end of this node.\n        // On a crossed boundary, we close new marks (inner) first, then old marks (outer),\n        // ensuring correct nesting order. Both sets are removed from activeMarks so the\n        // next node's marksToOpen will reopen whichever ones continue.\n        let marksToCloseAtEnd: string[]\n        if (hasCrossedBoundary) {\n          const nextMarkTypes = new Set((nextNode?.marks || []).map((mark: any) => mark.type))\n\n          marksToOpen.forEach(({ type }) => {\n            if (nextMarkTypes.has(type) && this.getHtmlReopenTags(type)) {\n              reopenWithHtmlOnNextOpen.add(type)\n            }\n          })\n\n          marksToCloseAtEnd = [\n            ...marksToOpen.map(m => m.type), // inner (opened here) — close first\n            ...activeMarksClosingHere, // outer (were active before) — close last\n          ]\n        } else {\n          marksToCloseAtEnd = findMarksToCloseAtEnd(activeMarks, currentMarks, nextNode, this.markSetsEqual.bind(this))\n        }\n\n        // Extract trailing whitespace before closing marks to prevent invalid markdown like \"**text **\"\n        let trailingWhitespace = ''\n        if (marksToCloseAtEnd.length > 0) {\n          const trailingMatch = textContent.match(/(\\s+)$/)\n          if (trailingMatch) {\n            trailingWhitespace = trailingMatch[1]\n            textContent = textContent.slice(0, -trailingWhitespace.length)\n          }\n        }\n\n        marksToCloseAtEnd.forEach(markType => {\n          const mark = activeMarks.get(markType) ?? currentMarks.get(markType)\n          const closeMarkdown = this.getMarkClosing(markType, mark, markOpeningModes.get(markType))\n          if (closeMarkdown) {\n            textContent += closeMarkdown\n          }\n          activeMarks.delete(markType)\n          markOpeningModes.delete(markType)\n        })\n\n        // Add trailing whitespace after the mark closing\n        textContent += trailingWhitespace\n        textContent += middleTrailingWhitespace\n\n        result.push(textContent)\n      } else {\n        // For non-text nodes, close all active marks before rendering, then reopen after\n        const marksToReopen = new Map(activeMarks)\n        const openingModesToReopen = new Map(markOpeningModes)\n\n        // Close all marks before the node\n        const beforeMarkdown = closeMarksBeforeNode(activeMarks, (markType, mark) => {\n          return this.getMarkClosing(markType, mark, markOpeningModes.get(markType))\n        })\n        markOpeningModes.clear()\n\n        // Render the node\n        const nodeContent = this.renderNodeToMarkdown(node, parentNode, i, level)\n\n        // Reopen marks after the node, but NOT after a hard break\n        // Hard breaks should terminate marks (they create a line break where marks don't continue)\n        const afterMarkdown =\n          node.type === 'hardBreak'\n            ? ''\n            : reopenMarksAfterNode(marksToReopen, activeMarks, (markType, mark) => {\n                const openingMode = openingModesToReopen.get(markType) ?? 'markdown'\n                markOpeningModes.set(markType, openingMode)\n                return this.getMarkOpening(markType, mark, openingMode)\n              })\n\n        result.push(beforeMarkdown + nodeContent + afterMarkdown)\n      }\n    })\n\n    return result.join(separator)\n  }\n\n  /**\n   * Get the opening markdown syntax for a mark type.\n   */\n  private getMarkOpening(markType: string, mark: any, openingMode: 'markdown' | 'html' = 'markdown'): string {\n    if (openingMode === 'html') {\n      return this.getHtmlReopenTags(markType)?.open || ''\n    }\n\n    const handlers = this.getHandlersForNodeType(markType)\n    const handler = handlers.length > 0 ? handlers[0] : undefined\n    if (!handler || !handler.renderMarkdown) {\n      return ''\n    }\n\n    // Use a unique placeholder that's extremely unlikely to appear in real content\n    const placeholder = '\\uE000__TIPTAP_MARKDOWN_PLACEHOLDER__\\uE001'\n\n    // For most marks, we can extract the opening syntax by rendering a simple case\n    const syntheticNode: JSONContent = {\n      type: markType,\n      attrs: mark.attrs || {},\n      content: [{ type: 'text', text: placeholder }],\n    }\n\n    try {\n      const rendered = handler.renderMarkdown(\n        syntheticNode,\n        {\n          renderChildren: () => placeholder,\n          renderChild: () => placeholder,\n          indent: (content: string) => content,\n          wrapInBlock: (prefix: string, content: string) => prefix + content,\n        },\n        { index: 0, level: 0, parentType: 'text', meta: {} },\n      )\n\n      // Extract the opening part (everything before placeholder)\n      const placeholderIndex = rendered.indexOf(placeholder)\n      return placeholderIndex >= 0 ? rendered.substring(0, placeholderIndex) : ''\n    } catch (err) {\n      throw new Error(`Failed to get mark opening for ${markType}: ${err}`)\n    }\n  }\n\n  /**\n   * Get the closing markdown syntax for a mark type.\n   */\n  private getMarkClosing(markType: string, mark: any, openingMode: 'markdown' | 'html' = 'markdown'): string {\n    if (openingMode === 'html') {\n      return this.getHtmlReopenTags(markType)?.close || ''\n    }\n\n    const handlers = this.getHandlersForNodeType(markType)\n    const handler = handlers.length > 0 ? handlers[0] : undefined\n    if (!handler || !handler.renderMarkdown) {\n      return ''\n    }\n\n    // Use a unique placeholder that's extremely unlikely to appear in real content\n    const placeholder = '\\uE000__TIPTAP_MARKDOWN_PLACEHOLDER__\\uE001'\n\n    const syntheticNode: JSONContent = {\n      type: markType,\n      attrs: mark.attrs || {},\n      content: [{ type: 'text', text: placeholder }],\n    }\n\n    try {\n      const rendered = handler.renderMarkdown(\n        syntheticNode,\n        {\n          renderChildren: () => placeholder,\n          renderChild: () => placeholder,\n          indent: (content: string) => content,\n          wrapInBlock: (prefix: string, content: string) => prefix + content,\n        },\n        { index: 0, level: 0, parentType: 'text', meta: {} },\n      )\n\n      // Extract the closing part (everything after placeholder)\n      const placeholderIndex = rendered.indexOf(placeholder)\n      const placeholderEnd = placeholderIndex + placeholder.length\n      return placeholderIndex >= 0 ? rendered.substring(placeholderEnd) : ''\n    } catch (err) {\n      throw new Error(`Failed to get mark closing for ${markType}: ${err}`)\n    }\n  }\n\n  /**\n   * Returns the inline HTML tags an extension exposes for overlap-boundary\n   * reopen handling, if that mark explicitly opted into HTML reopen mode.\n   */\n  private getHtmlReopenTags(markType: string): { open: string; close: string } | undefined {\n    const handlers = this.getHandlersForNodeType(markType)\n    const handler = handlers.length > 0 ? handlers[0] : undefined\n\n    return handler?.htmlReopen\n  }\n\n  /**\n   * Check if two mark sets are equal.\n   */\n  private markSetsEqual(marks1: Map<string, any>, marks2: Map<string, any>): boolean {\n    if (marks1.size !== marks2.size) {\n      return false\n    }\n\n    return Array.from(marks1.keys()).every(type => marks2.has(type))\n  }\n}\n\nexport default MarkdownManager\n","import type { Content, MarkdownToken } from '@tiptap/core'\nimport type { Fragment, Node } from '@tiptap/pm/model'\n\nimport type { ContentType } from './types.js'\n\n/**\n * Wraps each line of the content with the given prefix.\n * @param prefix The prefix to wrap each line with.\n * @param content The content to wrap.\n * @returns The content with each line wrapped with the prefix.\n */\nexport function wrapInMarkdownBlock(prefix: string, content: string) {\n  // split content lines\n  const lines = content.split('\\n')\n\n  // add empty strings between every line\n  const output = lines\n    // add empty lines between each block\n    .flatMap(line => [line, ''])\n    // add the prefix to each line\n    .map(line => `${prefix}${line}`)\n    .join('\\n')\n\n  return output.slice(0, output.length - 1)\n}\n\n/**\n * Identifies marks that need to be closed, based on the marks in the next node.\n */\nexport function findMarksToClose(currentMarks: Map<string, any>, nextNode: any): string[] {\n  const marksToClose: string[] = []\n\n  Array.from(currentMarks.keys()).forEach(markType => {\n    if (!nextNode || !nextNode.marks || !nextNode.marks.map((mark: any) => mark.type).includes(markType)) {\n      marksToClose.push(markType)\n    }\n  })\n  return marksToClose\n}\n\n/**\n * Identifies marks that need to be opened (in current node but not active).\n */\nexport function findMarksToOpen(\n  activeMarks: Map<string, any>,\n  currentMarks: Map<string, any>,\n): Array<{ type: string; mark: any }> {\n  const marksToOpen: Array<{ type: string; mark: any }> = []\n  Array.from(currentMarks.entries()).forEach(([markType, mark]) => {\n    if (!activeMarks.has(markType)) {\n      marksToOpen.push({ type: markType, mark })\n    }\n  })\n  return marksToOpen\n}\n\n/**\n * Determines which marks need to be closed at the end of the current text node.\n * This handles cases where marks end at node boundaries or when transitioning\n * to nodes with different mark sets.\n */\nexport function findMarksToCloseAtEnd(\n  activeMarks: Map<string, any>,\n  currentMarks: Map<string, any>,\n  nextNode: any,\n  markSetsEqual: (a: Map<string, any>, b: Map<string, any>) => boolean,\n): string[] {\n  const isLastNode = !nextNode\n  const nextNodeHasNoMarks = nextNode && nextNode.type === 'text' && (!nextNode.marks || nextNode.marks.length === 0)\n  const nextNodeHasDifferentMarks =\n    nextNode &&\n    nextNode.type === 'text' &&\n    nextNode.marks &&\n    !markSetsEqual(currentMarks, new Map(nextNode.marks.map((mark: any) => [mark.type, mark])))\n\n  const marksToCloseAtEnd: string[] = []\n  if (isLastNode || nextNodeHasNoMarks || nextNodeHasDifferentMarks) {\n    if (nextNode && nextNode.type === 'text' && nextNode.marks) {\n      const nextMarks = new Map(nextNode.marks.map((mark: any) => [mark.type, mark]))\n      Array.from(activeMarks.keys())\n        .reverse()\n        .forEach(markType => {\n          if (!nextMarks.has(markType)) {\n            marksToCloseAtEnd.push(markType)\n          }\n        })\n    } else if (isLastNode || nextNodeHasNoMarks) {\n      // Close all active marks\n      marksToCloseAtEnd.push(...Array.from(activeMarks.keys()).reverse())\n    }\n  }\n\n  return marksToCloseAtEnd\n}\n\n/**\n * Closes active marks before rendering a non-text node.\n * Returns the closing markdown syntax and clears the active marks.\n */\nexport function closeMarksBeforeNode(\n  activeMarks: Map<string, any>,\n  getMarkClosing: (markType: string, mark: any) => string,\n): string {\n  let beforeMarkdown = ''\n  Array.from(activeMarks.keys())\n    .reverse()\n    .forEach(markType => {\n      const mark = activeMarks.get(markType)\n      const closeMarkdown = getMarkClosing(markType, mark)\n      if (closeMarkdown) {\n        beforeMarkdown = closeMarkdown + beforeMarkdown\n      }\n    })\n  activeMarks.clear()\n  return beforeMarkdown\n}\n\n/**\n * Reopens marks after rendering a non-text node.\n * Returns the opening markdown syntax and updates the active marks.\n */\nexport function reopenMarksAfterNode(\n  marksToReopen: Map<string, any>,\n  activeMarks: Map<string, any>,\n  getMarkOpening: (markType: string, mark: any) => string,\n): string {\n  let afterMarkdown = ''\n  Array.from(marksToReopen.entries()).forEach(([markType, mark]) => {\n    const openMarkdown = getMarkOpening(markType, mark)\n    if (openMarkdown) {\n      afterMarkdown += openMarkdown\n    }\n    activeMarks.set(markType, mark)\n  })\n  return afterMarkdown\n}\n\n/**\n * Check if a markdown list item token is a task item and extract its state.\n *\n * @param item The list item token to check\n * @returns Object containing isTask flag, checked state, and indentation level\n *\n * @example\n * ```ts\n * isTaskItem({ raw: '- [ ] Task' }) // { isTask: true, checked: false, indentLevel: 0 }\n * isTaskItem({ raw: '  - [x] Done' }) // { isTask: true, checked: true, indentLevel: 2 }\n * isTaskItem({ raw: '- Regular' }) // { isTask: false, indentLevel: 0 }\n * ```\n */\nexport function isTaskItem(item: MarkdownToken): { isTask: boolean; checked?: boolean; indentLevel: number } {\n  const raw = item.raw || item.text || ''\n\n  // Match patterns like \"- [ ] \" or \"  - [x] \"\n  const match = raw.match(/^(\\s*)[-+*]\\s+\\[([ xX])\\]\\s+/)\n\n  if (match) {\n    return { isTask: true, checked: match[2].toLowerCase() === 'x', indentLevel: match[1].length }\n  }\n  return { isTask: false, indentLevel: 0 }\n}\n\n/**\n * Assumes the content type based off the content.\n * @param content The content to assume the type for.\n * @param contentType The content type that should be prioritized.\n */\nexport function assumeContentType(\n  content: (Content | Fragment | Node) | string,\n  contentType: ContentType,\n): ContentType {\n  // if not a string, we assume it will be a json content object\n  if (typeof content !== 'string') {\n    return 'json'\n  }\n\n  // otherwise we let the content type be what it is\n  return contentType\n}\n"]}

package/dist/index.d.cts

@@ -4,7 +4,7 @@ import { Fragment, Node } from '@tiptap/pm/model';
 
 declare class MarkdownManager {
     private markedInstance;
-    private lexer;
+    private activeParseLexer;
     private registry;
     private nodeTypeRegistry;
     private indentStyle;
@@ -40,7 +40,10 @@ declare class MarkdownManager {
      * `markdownName`, `parseMarkdown`, `renderMarkdown` and `priority` from the
      * extension config (using the same resolution used across the codebase).
      */
-    registerExtension(extension: AnyExtension, recreateLexer?: boolean): void;
+    registerExtension(extension: AnyExtension): void;
+    private createLexer;
+    private createTokenizerHelpers;
+    private tokenizeInline;
     /**
      * Register a custom tokenizer with marked.js for parsing non-standard markdown syntax.
      */

package/dist/index.d.ts

@@ -4,7 +4,7 @@ import { Fragment, Node } from '@tiptap/pm/model';
 
 declare class MarkdownManager {
     private markedInstance;
-    private lexer;
+    private activeParseLexer;
     private registry;
     private nodeTypeRegistry;
     private indentStyle;
@@ -40,7 +40,10 @@ declare class MarkdownManager {
      * `markdownName`, `parseMarkdown`, `renderMarkdown` and `priority` from the
      * extension config (using the same resolution used across the codebase).
      */
-    registerExtension(extension: AnyExtension, recreateLexer?: boolean): void;
+    registerExtension(extension: AnyExtension): void;
+    private createLexer;
+    private createTokenizerHelpers;
+    private tokenizeInline;
     /**
      * Register a custom tokenizer with marked.js for parsing non-standard markdown syntax.
      */

package/dist/index.js

@@ -103,12 +103,12 @@ var MarkdownManager = class {
    * @param options.extensions An array of Tiptap extensions to register for markdown parsing and rendering.
    */
   constructor(options) {
+    this.activeParseLexer = null;
     this.baseExtensions = [];
     this.extensions = [];
     this.lastParseResult = null;
     var _a, _b, _c, _d, _e;
     this.markedInstance = (_a = options == null ? void 0 : options.marked) != null ? _a : marked;
-    this.lexer = new this.markedInstance.Lexer();
     this.indentStyle = (_c = (_b = options == null ? void 0 : options.indentation) == null ? void 0 : _b.style) != null ? _c : "space";
     this.indentSize = (_e = (_d = options == null ? void 0 : options.indentation) == null ? void 0 : _d.size) != null ? _e : 2;
     this.baseExtensions = (options == null ? void 0 : options.extensions) || [];
@@ -120,9 +120,8 @@ var MarkdownManager = class {
     if (options == null ? void 0 : options.extensions) {
       this.baseExtensions = options.extensions;
       const flattened = flattenExtensions(options.extensions);
-      flattened.forEach((ext) => this.registerExtension(ext, false));
+      flattened.forEach((ext) => this.registerExtension(ext));
     }
-    this.lexer = new this.markedInstance.Lexer();
   }
   /** Returns the underlying marked instance. */
   get instance() {
@@ -145,7 +144,7 @@ var MarkdownManager = class {
    * `markdownName`, `parseMarkdown`, `renderMarkdown` and `priority` from the
    * extension config (using the same resolution used across the codebase).
    */
-  registerExtension(extension, recreateLexer = true) {
+  registerExtension(extension) {
     var _a, _b;
     this.extensions.push(extension);
     const name = extension.name;
@@ -177,11 +176,21 @@ var MarkdownManager = class {
     }
     if (tokenizer && this.hasMarked()) {
       this.registerTokenizer(tokenizer);
-      if (recreateLexer) {
-        this.lexer = new this.markedInstance.Lexer();
-      }
     }
   }
+  createLexer() {
+    return new this.markedInstance.Lexer();
+  }
+  createTokenizerHelpers(lexer) {
+    return {
+      inlineTokens: (src) => lexer.inlineTokens(src),
+      blockTokens: (src) => lexer.blockTokens(src)
+    };
+  }
+  tokenizeInline(src) {
+    var _a;
+    return ((_a = this.activeParseLexer) != null ? _a : this.createLexer()).inlineTokens(src);
+  }
   /**
    * Register a custom tokenizer with marked.js for parsing non-standard markdown syntax.
    */
@@ -190,20 +199,12 @@ var MarkdownManager = class {
       return;
     }
     const { name, start, level = "inline", tokenize } = tokenizer;
-    const tokenizeInline = (src) => {
-      return this.lexer.inlineTokens(src);
-    };
-    const tokenizeBlock = (src) => {
-      return this.lexer.blockTokens(src);
-    };
-    const helper = {
-      inlineTokens: tokenizeInline,
-      blockTokens: tokenizeBlock
-    };
+    const createTokenizerHelpers = this.createTokenizerHelpers.bind(this);
+    const createLexer = this.createLexer.bind(this);
     let startCb;
     if (!start) {
       startCb = (src) => {
-        const result = tokenize(src, [], helper);
+        const result = tokenize(src, [], this.createTokenizerHelpers(this.createLexer()));
         if (result && result.raw) {
           const index = src.indexOf(result.raw);
           return index;
@@ -217,7 +218,8 @@ var MarkdownManager = class {
       name,
       level,
       start: startCb,
-      tokenizer: (src, tokens) => {
+      tokenizer(src, tokens) {
+        const helper = this.lexer ? createTokenizerHelpers(this.lexer) : createTokenizerHelpers(createLexer());
         const result = tokenize(src, tokens, helper);
         if (result && result.type) {
           return {
@@ -290,12 +292,19 @@ var MarkdownManager = class {
     if (!this.hasMarked()) {
       throw new Error("No marked instance available for parsing");
     }
-    const tokens = this.markedInstance.lexer(markdown);
-    const content = this.parseTokens(tokens, true);
-    return {
-      type: "doc",
-      content
-    };
+    const previousParseLexer = this.activeParseLexer;
+    const parseLexer = this.createLexer();
+    this.activeParseLexer = parseLexer;
+    try {
+      const tokens = parseLexer.lex(markdown);
+      const content = this.parseTokens(tokens, true);
+      return {
+        type: "doc",
+        content
+      };
+    } finally {
+      this.activeParseLexer = previousParseLexer;
+    }
   }
   /**
    * Convert an array of marked tokens into Tiptap JSON nodes using registered extension handlers.
@@ -426,7 +435,7 @@ var MarkdownManager = class {
           indentLevel,
           checked: checked != null ? checked : false,
           text: mainContent,
-          tokens: this.lexer.inlineTokens(mainContent),
+          tokens: this.tokenizeInline(mainContent),
           nestedTokens
         };
       }

package/dist/index.js.map

@@ -1 +1 @@
-{"version":3,"sources":["../src/Extension.ts","../src/MarkdownManager.ts","../src/utils.ts"],"sourcesContent":["import {\n  type InsertContentAtOptions as MarkdownInsertContentAtOptions,\n  type InsertContentOptions as MarkdownInsertContentOptions,\n  type SetContentOptions as MarkdownSetContentOptions,\n  commands,\n  Extension,\n} from '@tiptap/core'\nimport type { marked } from 'marked'\n\nimport MarkdownManager from './MarkdownManager.js'\nimport type { ContentType } from './types.js'\nimport { assumeContentType } from './utils.js'\n\ndeclare module '@tiptap/core' {\n  interface Editor {\n    /**\n     * Get the content of the editor as markdown.\n     */\n    getMarkdown: () => string\n\n    /**\n     * The markdown manager instance.\n     */\n    markdown?: MarkdownManager\n  }\n\n  interface EditorOptions {\n    /**\n     * The content type the content is provided as.\n     *\n     * @default 'json'\n     */\n    contentType?: ContentType\n  }\n\n  interface Storage {\n    markdown: MarkdownExtensionStorage\n  }\n\n  interface InsertContentOptions {\n    /**\n     * The content type the content is provided as.\n     *\n     * @default 'json'\n     */\n    contentType?: ContentType\n  }\n\n  interface InsertContentAtOptions {\n    /**\n     * The content type the content is provided as.\n     *\n     * @default 'json'\n     */\n    contentType?: ContentType\n  }\n\n  interface SetContentOptions {\n    /**\n     * The content type the content is provided as.\n     *\n     * @default 'json'\n     */\n    contentType?: ContentType\n  }\n}\n\nexport type MarkdownExtensionOptions = {\n  /**\n   * Configure the indentation style and size for lists and code blocks.\n   * - `style`: Choose between spaces or tabs. Default is 'space'.\n   * - `size`: Number of spaces or tabs for indentation. Default is 2.\n   */\n  indentation?: { style?: 'space' | 'tab'; size?: number }\n\n  /**\n   * Use a custom version of `marked` for markdown parsing and serialization.\n   * If not provided, the default `marked` instance will be used.\n   */\n  marked?: typeof marked\n\n  /**\n   * Options to pass to `marked.setOptions()`.\n   * See the [marked documentation](https://marked.js.org/using_advanced#options) for available options.\n   */\n  markedOptions?: Parameters<typeof marked.setOptions>[0]\n}\n\nexport type MarkdownExtensionStorage = {\n  manager: MarkdownManager\n}\n\nexport const Markdown = Extension.create<MarkdownExtensionOptions, MarkdownExtensionStorage>({\n  name: 'markdown',\n\n  addOptions() {\n    return {\n      indentation: { style: 'space', size: 2 },\n      marked: undefined,\n      markedOptions: {},\n    }\n  },\n\n  addCommands() {\n    return {\n      setContent: (content, options?: MarkdownSetContentOptions) => {\n        // if no contentType is specified, we assume the content is in JSON format OR HTML format\n        if (!options?.contentType) {\n          return commands.setContent(content, options)\n        }\n\n        const actualContentType = assumeContentType(content, options?.contentType)\n\n        if (actualContentType !== 'markdown' || !this.editor.markdown) {\n          return commands.setContent(content, options)\n        }\n\n        const mdContent = this.editor.markdown.parse(content as string)\n        return commands.setContent(mdContent, options)\n      },\n\n      insertContent: (value, options?: MarkdownInsertContentOptions) => {\n        // if no contentType is specified, we assume the content is in JSON format OR HTML format\n        if (!options?.contentType) {\n          return commands.insertContent(value, options)\n        }\n\n        const actualContentType = assumeContentType(value, options?.contentType)\n\n        if (actualContentType !== 'markdown' || !this.editor.markdown) {\n          return commands.insertContent(value, options)\n        }\n\n        const mdContent = this.editor.markdown.parse(value as string)\n        return commands.insertContent(mdContent, options)\n      },\n\n      insertContentAt: (position, value, options?: MarkdownInsertContentAtOptions) => {\n        // if no contentType is specified, we assume the content is in JSON format OR HTML format\n        if (!options?.contentType) {\n          return commands.insertContentAt(position, value, options)\n        }\n\n        const actualContentType = assumeContentType(value, options?.contentType)\n\n        if (actualContentType !== 'markdown' || !this.editor.markdown) {\n          return commands.insertContentAt(position, value, options)\n        }\n\n        const mdContent = this.editor.markdown.parse(value as string)\n        return commands.insertContentAt(position, mdContent, options)\n      },\n    }\n  },\n\n  addStorage() {\n    return {\n      manager: new MarkdownManager({\n        indentation: this.options.indentation,\n        marked: this.options.marked,\n        markedOptions: this.options.markedOptions,\n        extensions: [],\n      }),\n    }\n  },\n\n  onBeforeCreate() {\n    if (this.editor.markdown) {\n      console.error(\n        '[tiptap][markdown]: There is already a `markdown` property on the editor instance. This might lead to unexpected behavior.',\n      )\n      return\n    }\n\n    this.storage.manager = new MarkdownManager({\n      indentation: this.options.indentation,\n      marked: this.options.marked,\n      markedOptions: this.options.markedOptions,\n      extensions: this.editor.extensionManager.baseExtensions,\n    })\n\n    this.editor.markdown = this.storage.manager\n\n    // add a `getMarkdown()` method to the editor\n    this.editor.getMarkdown = () => {\n      return this.storage.manager.serialize(this.editor.getJSON())\n    }\n\n    if (!this.editor.options.contentType) {\n      return\n    }\n\n    const assumedType = assumeContentType(this.editor.options.content, this.editor.options.contentType)\n    if (assumedType !== 'markdown') {\n      return\n    }\n\n    if (!this.editor.markdown) {\n      throw new Error(\n        '[tiptap][markdown]: The `contentType` option is set to \"markdown\", but the Markdown extension is not added to the editor. Please add the Markdown extension to use this feature.',\n      )\n    }\n\n    if (this.editor.options.content === undefined || typeof this.editor.options.content !== 'string') {\n      throw new Error(\n        '[tiptap][markdown]: The `contentType` option is set to \"markdown\", but the initial content is not a string. Please provide the initial content as a markdown string.',\n      )\n    }\n\n    const json = this.editor.markdown.parse(this.editor.options.content as string)\n    this.editor.options.content = json\n  },\n})\n","import {\n  type AnyExtension,\n  type ExtendableConfig,\n  type JSONContent,\n  type MarkdownExtensionSpec,\n  type MarkdownParseHelpers,\n  type MarkdownParseResult,\n  type MarkdownRendererHelpers,\n  type MarkdownToken,\n  type MarkdownTokenizer,\n  type RenderContext,\n  flattenExtensions,\n  generateJSON,\n  getExtensionField,\n} from '@tiptap/core'\nimport { type Lexer, type Token, type TokenizerExtension, marked } from 'marked'\n\nimport {\n  closeMarksBeforeNode,\n  findMarksToClose,\n  findMarksToCloseAtEnd,\n  findMarksToOpen,\n  isTaskItem,\n  reopenMarksAfterNode,\n  wrapInMarkdownBlock,\n} from './utils.js'\n\nexport class MarkdownManager {\n  private markedInstance: typeof marked\n  private lexer: Lexer\n  private registry: Map<string, MarkdownExtensionSpec[]>\n  private nodeTypeRegistry: Map<string, MarkdownExtensionSpec[]>\n  private indentStyle: 'space' | 'tab'\n  private indentSize: number\n  private baseExtensions: AnyExtension[] = []\n  private extensions: AnyExtension[] = []\n\n  /**\n   * Create a MarkdownManager.\n   * @param options.marked Optional marked instance to use (injected).\n   * @param options.markedOptions Optional options to pass to marked.setOptions\n   * @param options.indentation Indentation settings (style and size).\n   * @param options.extensions An array of Tiptap extensions to register for markdown parsing and rendering.\n   */\n  constructor(options?: {\n    marked?: typeof marked\n    markedOptions?: Parameters<typeof marked.setOptions>[0]\n    indentation?: { style?: 'space' | 'tab'; size?: number }\n    extensions: AnyExtension[]\n  }) {\n    this.markedInstance = options?.marked ?? marked\n    this.lexer = new this.markedInstance.Lexer()\n    this.indentStyle = options?.indentation?.style ?? 'space'\n    this.indentSize = options?.indentation?.size ?? 2\n    this.baseExtensions = options?.extensions || []\n\n    if (options?.markedOptions && typeof this.markedInstance.setOptions === 'function') {\n      this.markedInstance.setOptions(options.markedOptions)\n    }\n\n    this.registry = new Map()\n    this.nodeTypeRegistry = new Map()\n\n    // If extensions were provided, register them now\n    if (options?.extensions) {\n      this.baseExtensions = options.extensions\n      const flattened = flattenExtensions(options.extensions)\n      flattened.forEach(ext => this.registerExtension(ext, false))\n    }\n    this.lexer = new this.markedInstance.Lexer() // Reset lexer to include all tokenizers\n  }\n\n  /** Returns the underlying marked instance. */\n  get instance(): typeof marked {\n    return this.markedInstance\n  }\n\n  /** Returns the correct indentCharacter (space or tab) */\n  get indentCharacter(): string {\n    return this.indentStyle === 'space' ? ' ' : '\\t'\n  }\n\n  /** Returns the correct indentString repeated X times */\n  get indentString(): string {\n    return this.indentCharacter.repeat(this.indentSize)\n  }\n\n  /** Helper to quickly check whether a marked instance is available. */\n  hasMarked(): boolean {\n    return !!this.markedInstance\n  }\n\n  /**\n   * Register a Tiptap extension (Node/Mark/Extension). This will read\n   * `markdownName`, `parseMarkdown`, `renderMarkdown` and `priority` from the\n   * extension config (using the same resolution used across the codebase).\n   */\n  registerExtension(extension: AnyExtension, recreateLexer: boolean = true): void {\n    // Keep track of all extensions for HTML parsing\n    this.extensions.push(extension)\n\n    const name = extension.name\n    const tokenName =\n      (getExtensionField(extension, 'markdownTokenName') as ExtendableConfig['markdownTokenName']) || name\n    const parseMarkdown = getExtensionField(extension, 'parseMarkdown') as ExtendableConfig['parseMarkdown'] | undefined\n    const renderMarkdown = getExtensionField(extension, 'renderMarkdown') as\n      | ExtendableConfig['renderMarkdown']\n      | undefined\n    const tokenizer = getExtensionField(extension, 'markdownTokenizer') as\n      | ExtendableConfig['markdownTokenizer']\n      | undefined\n\n    // Read the `markdown` object from the extension config. This allows\n    // extensions to provide `markdown: { name?, parseName?, renderName?, parse?, render?, match? }`.\n    const markdownCfg = (getExtensionField(extension, 'markdownOptions') ?? null) as ExtendableConfig['markdownOptions']\n    const isIndenting = markdownCfg?.indentsContent ?? false\n    const htmlReopen = markdownCfg?.htmlReopen\n\n    const spec: MarkdownExtensionSpec = {\n      tokenName,\n      nodeName: name,\n      parseMarkdown,\n      renderMarkdown,\n      isIndenting,\n      htmlReopen,\n      tokenizer,\n    }\n\n    // Add to parse registry using parseName\n    if (tokenName && parseMarkdown) {\n      const parseExisting = this.registry.get(tokenName) || []\n      parseExisting.push(spec)\n      this.registry.set(tokenName, parseExisting)\n    }\n\n    // Add to render registry using renderName (node type)\n    if (renderMarkdown) {\n      const renderExisting = this.nodeTypeRegistry.get(name) || []\n      renderExisting.push(spec)\n      this.nodeTypeRegistry.set(name, renderExisting)\n    }\n\n    // Register custom tokenizer with marked.js\n    if (tokenizer && this.hasMarked()) {\n      this.registerTokenizer(tokenizer)\n\n      if (recreateLexer) {\n        this.lexer = new this.markedInstance.Lexer() // Reset lexer to include new tokenizer\n      }\n    }\n  }\n\n  /**\n   * Register a custom tokenizer with marked.js for parsing non-standard markdown syntax.\n   */\n  private registerTokenizer(tokenizer: MarkdownTokenizer): void {\n    if (!this.hasMarked()) {\n      return\n    }\n\n    const { name, start, level = 'inline', tokenize } = tokenizer\n\n    // Helper functions that use a fresh lexer instance with all registered extensions\n    const tokenizeInline = (src: string) => {\n      return this.lexer.inlineTokens(src)\n    }\n\n    const tokenizeBlock = (src: string) => {\n      return this.lexer.blockTokens(src)\n    }\n\n    const helper = {\n      inlineTokens: tokenizeInline,\n      blockTokens: tokenizeBlock,\n    }\n\n    let startCb: (src: string) => number\n\n    if (!start) {\n      startCb = (src: string) => {\n        // For other tokenizers, try to find a match and return its position\n        const result = tokenize(src, [], helper)\n        if (result && result.raw) {\n          const index = src.indexOf(result.raw)\n          return index\n        }\n        return -1\n      }\n    } else {\n      startCb = typeof start === 'function' ? start : (src: string) => src.indexOf(start)\n    }\n\n    // Create marked.js extension with proper types\n    const markedExtension: TokenizerExtension = {\n      name,\n      level,\n      start: startCb,\n      tokenizer: (src, tokens) => {\n        const result = tokenize(src, tokens, helper)\n\n        if (result && result.type) {\n          return {\n            ...result,\n            type: result.type || name,\n            raw: result.raw || '',\n            tokens: (result.tokens || []) as Token[],\n          }\n        }\n\n        return undefined\n      },\n      childTokens: [],\n    }\n\n    // Register with marked.js - use extensions array to control priority\n    this.markedInstance.use({\n      extensions: [markedExtension],\n    })\n  }\n\n  /** Get registered handlers for a token type and try each until one succeeds. */\n  private getHandlersForToken(type: string): MarkdownExtensionSpec[] {\n    try {\n      return this.registry.get(type) || []\n    } catch {\n      return []\n    }\n  }\n\n  /** Get the first handler for a token type (for backwards compatibility). */\n  private getHandlerForToken(type: string): MarkdownExtensionSpec | undefined {\n    // First try the markdown token registry (for parsing)\n    const markdownHandlers = this.getHandlersForToken(type)\n    if (markdownHandlers.length > 0) {\n      return markdownHandlers[0]\n    }\n\n    // Then try the node type registry (for rendering)\n    const nodeTypeHandlers = this.getHandlersForNodeType(type)\n    return nodeTypeHandlers.length > 0 ? nodeTypeHandlers[0] : undefined\n  }\n\n  /** Get registered handlers for a node type (for rendering). */\n  private getHandlersForNodeType(type: string): MarkdownExtensionSpec[] {\n    try {\n      return this.nodeTypeRegistry.get(type) || []\n    } catch {\n      return []\n    }\n  }\n\n  /**\n   * Serialize a ProseMirror-like JSON document (or node array) to a Markdown string\n   * using registered renderers and fallback renderers.\n   */\n  serialize(docOrContent: JSONContent): string {\n    if (!docOrContent) {\n      return ''\n    }\n\n    const result = this.renderNodes(docOrContent, docOrContent)\n    // Return empty string if result is only whitespace entities or non-breaking spaces\n    return this.isEmptyOutput(result) ? '' : result\n  }\n\n  /**\n   * Check if the markdown output represents an empty document.\n   * Empty documents may contain only &nbsp; entities or non-breaking space characters\n   * which are used by the Paragraph extension to preserve blank lines.\n   */\n  private isEmptyOutput(markdown: string): boolean {\n    if (!markdown || markdown.trim() === '') {\n      return true\n    }\n\n    // Check if the output is only &nbsp; entities or non-breaking space characters\n    const cleanedOutput = markdown\n      .replace(/&nbsp;/g, '')\n      .replace(/\\u00A0/g, '')\n      .trim()\n    return cleanedOutput === ''\n  }\n\n  /**\n   * Parse markdown string into Tiptap JSON document using registered extension handlers.\n   */\n  parse(markdown: string): JSONContent {\n    if (!this.hasMarked()) {\n      throw new Error('No marked instance available for parsing')\n    }\n\n    // Use marked to tokenize the markdown\n    const tokens = this.markedInstance.lexer(markdown)\n\n    // Convert tokens to Tiptap JSON\n    const content = this.parseTokens(tokens, true)\n\n    // Return a document node containing the parsed content\n    return {\n      type: 'doc',\n      content,\n    }\n  }\n\n  /**\n   * Convert an array of marked tokens into Tiptap JSON nodes using registered extension handlers.\n   */\n  private parseTokens(tokens: MarkdownToken[], parseImplicitEmptyParagraphs = false): JSONContent[] {\n    const nonSpaceTokenIndexes = tokens.reduce<number[]>((indexes, token, index) => {\n      if (token.type !== 'space') {\n        indexes.push(index)\n      }\n\n      return indexes\n    }, [])\n\n    let previousNonSpaceTokenIndex = -1\n    let nextNonSpaceTokenPointer = 0\n\n    return tokens.flatMap((token, index) => {\n      while (\n        nextNonSpaceTokenPointer < nonSpaceTokenIndexes.length &&\n        nonSpaceTokenIndexes[nextNonSpaceTokenPointer] < index\n      ) {\n        previousNonSpaceTokenIndex = nonSpaceTokenIndexes[nextNonSpaceTokenPointer]\n        nextNonSpaceTokenPointer += 1\n      }\n\n      if (parseImplicitEmptyParagraphs && token.type === 'space') {\n        const nextNonSpaceTokenIndex = nonSpaceTokenIndexes[nextNonSpaceTokenPointer] ?? -1\n\n        return this.createImplicitEmptyParagraphsFromSpace(token, previousNonSpaceTokenIndex, nextNonSpaceTokenIndex)\n      }\n\n      const parsed = this.parseToken(token, parseImplicitEmptyParagraphs)\n\n      if (parsed === null) {\n        return []\n      }\n\n      return Array.isArray(parsed) ? parsed : [parsed]\n    })\n  }\n\n  private createImplicitEmptyParagraphsFromSpace(\n    token: MarkdownToken,\n    previousNonSpaceTokenIndex: number,\n    nextNonSpaceTokenIndex: number,\n  ): JSONContent[] {\n    const separatorCount = this.countParagraphSeparators(token.raw || '')\n\n    if (separatorCount === 0) {\n      return []\n    }\n\n    const isBoundarySpace = previousNonSpaceTokenIndex === -1 || nextNonSpaceTokenIndex === -1\n    const emptyParagraphCount = Math.max(separatorCount - (isBoundarySpace ? 0 : 1), 0)\n\n    return Array.from({ length: emptyParagraphCount }, () => ({ type: 'paragraph', content: [] }))\n  }\n\n  private countParagraphSeparators(raw: string): number {\n    return (raw.replace(/\\r\\n/g, '\\n').match(/\\n\\n/g) || []).length\n  }\n\n  /**\n   * Parse a single token into Tiptap JSON using the appropriate registered handler.\n   */\n  private parseToken(token: MarkdownToken, parseImplicitEmptyParagraphs = false): JSONContent | JSONContent[] | null {\n    if (!token.type) {\n      return null\n    }\n\n    // Special handling for 'list' tokens that may contain mixed bullet/task items\n    if (token.type === 'list') {\n      return this.parseListToken(token)\n    }\n\n    const handlers = this.getHandlersForToken(token.type)\n    const helpers = this.createParseHelpers()\n\n    // Try each handler until one returns a valid result\n    const result = handlers.find(handler => {\n      if (!handler.parseMarkdown) {\n        return false\n      }\n\n      const parseResult = handler.parseMarkdown(token, helpers)\n      const normalized = this.normalizeParseResult(parseResult)\n\n      // Check if this handler returned a valid result (not null/empty array)\n      if (normalized && (!Array.isArray(normalized) || normalized.length > 0)) {\n        // Store result for return\n        this.lastParseResult = normalized\n        return true\n      }\n\n      return false\n    })\n\n    // If a handler worked, return its result\n    if (result && this.lastParseResult) {\n      const toReturn = this.lastParseResult\n      this.lastParseResult = null // Clean up\n      return toReturn\n    }\n\n    // If no handler worked, try fallback parsing\n    return this.parseFallbackToken(token, parseImplicitEmptyParagraphs)\n  }\n\n  private lastParseResult: JSONContent | JSONContent[] | null = null\n\n  /**\n   * Parse a list token, handling mixed bullet and task list items by splitting them into separate lists.\n   * This ensures that consecutive task items and bullet items are grouped and parsed as separate list nodes.\n   *\n   * @param token The list token to parse\n   * @returns Array of parsed list nodes, or null if parsing fails\n   */\n  private parseListToken(token: MarkdownToken): JSONContent | JSONContent[] | null {\n    if (!token.items || token.items.length === 0) {\n      // No items, parse normally\n      return this.parseTokenWithHandlers(token)\n    }\n\n    const hasTask = token.items.some(item => isTaskItem(item).isTask)\n    const hasNonTask = token.items.some(item => !isTaskItem(item).isTask)\n\n    if (!hasTask || !hasNonTask || this.getHandlersForToken('taskList').length === 0) {\n      // Not mixed or no taskList extension, parse normally\n      return this.parseTokenWithHandlers(token)\n    }\n\n    // Mixed list with taskList extension available: split into separate lists\n    type TaskListItemToken = MarkdownToken & { type: 'taskItem'; checked?: boolean; indentLevel?: number }\n    const groups: { type: 'list' | 'taskList'; items: (MarkdownToken | TaskListItemToken)[] }[] = []\n    let currentGroup: (MarkdownToken | TaskListItemToken)[] = []\n    let currentType: 'list' | 'taskList' | null = null\n\n    for (let i = 0; i < token.items.length; i += 1) {\n      const item = token.items[i]\n      const { isTask, checked, indentLevel } = isTaskItem(item)\n      let processedItem = item\n\n      if (isTask) {\n        // Transform list_item into taskItem token\n        const raw = item.raw || item.text || ''\n\n        // Split raw content by lines to separate main content from nested\n        const lines = raw.split('\\n')\n\n        // Extract main content from the first line\n        const firstLineMatch = lines[0].match(/^\\s*[-+*]\\s+\\[([ xX])\\]\\s+(.*)$/)\n        const mainContent = firstLineMatch ? firstLineMatch[2] : ''\n\n        // Parse nested content from remaining lines\n        let nestedTokens: MarkdownToken[] = []\n        if (lines.length > 1) {\n          // Join all lines after the first\n          const nestedRaw = lines.slice(1).join('\\n')\n\n          // Only parse if there's actual content\n          if (nestedRaw.trim()) {\n            // Find minimum indentation of non-empty lines\n            const nestedLines = lines.slice(1)\n            const nonEmptyLines = nestedLines.filter(line => line.trim())\n            if (nonEmptyLines.length > 0) {\n              const minIndent = Math.min(...nonEmptyLines.map(line => line.length - line.trimStart().length))\n              // Remove common indentation while preserving structure\n              const trimmedLines = nestedLines.map(line => {\n                if (!line.trim()) {\n                  return '' // Keep empty lines\n                }\n                return line.slice(minIndent)\n              })\n              const nestedContent = trimmedLines.join('\\n').trim()\n              // Use the lexer to parse nested content\n              if (nestedContent) {\n                // Use the full lexer pipeline to ensure inline tokens are populated\n                nestedTokens = this.markedInstance.lexer(`${nestedContent}\\n`)\n              }\n            }\n          }\n        }\n\n        processedItem = {\n          type: 'taskItem',\n          raw: '',\n          mainContent,\n          indentLevel,\n          checked: checked ?? false,\n          text: mainContent,\n          tokens: this.lexer.inlineTokens(mainContent),\n          nestedTokens,\n        }\n      }\n\n      const itemType: 'list' | 'taskList' = isTask ? 'taskList' : 'list'\n\n      if (currentType !== itemType) {\n        if (currentGroup.length > 0) {\n          groups.push({ type: currentType!, items: currentGroup })\n        }\n        currentGroup = [processedItem]\n        currentType = itemType\n      } else {\n        currentGroup.push(processedItem)\n      }\n    }\n\n    if (currentGroup.length > 0) {\n      groups.push({ type: currentType!, items: currentGroup })\n    }\n\n    // Parse each group as a separate token\n    const results: JSONContent[] = []\n    for (let i = 0; i < groups.length; i += 1) {\n      const group = groups[i]\n      const subToken = { ...token, type: group.type, items: group.items }\n      const parsed = this.parseToken(subToken)\n      if (parsed) {\n        if (Array.isArray(parsed)) {\n          results.push(...parsed)\n        } else {\n          results.push(parsed)\n        }\n      }\n    }\n\n    return results.length > 0 ? results : null\n  }\n\n  /**\n   * Parse a token using registered handlers (extracted for reuse).\n   */\n  private parseTokenWithHandlers(token: MarkdownToken): JSONContent | JSONContent[] | null {\n    if (!token.type) {\n      return null\n    }\n\n    const handlers = this.getHandlersForToken(token.type)\n    const helpers = this.createParseHelpers()\n\n    // Try each handler until one returns a valid result\n    const result = handlers.find(handler => {\n      if (!handler.parseMarkdown) {\n        return false\n      }\n\n      const parseResult = handler.parseMarkdown(token, helpers)\n      const normalized = this.normalizeParseResult(parseResult)\n\n      // Check if this handler returned a valid result (not null/empty array)\n      if (normalized && (!Array.isArray(normalized) || normalized.length > 0)) {\n        // Store result for return\n        this.lastParseResult = normalized\n        return true\n      }\n\n      return false\n    })\n\n    // If a handler worked, return its result\n    if (result && this.lastParseResult) {\n      const toReturn = this.lastParseResult\n      this.lastParseResult = null // Clean up\n      return toReturn\n    }\n\n    // If no handler worked, try fallback parsing\n    return this.parseFallbackToken(token)\n  }\n\n  /**\n   * Creates helper functions for parsing markdown tokens.\n   * @returns An object containing helper functions for parsing.\n   */\n  private createParseHelpers(): MarkdownParseHelpers {\n    return {\n      parseInline: (tokens: MarkdownToken[]) => this.parseInlineTokens(tokens),\n      parseChildren: (tokens: MarkdownToken[]) => this.parseTokens(tokens),\n      parseBlockChildren: (tokens: MarkdownToken[]) => this.parseTokens(tokens, true),\n      createTextNode: (text: string, marks?: Array<{ type: string; attrs?: any }>) => {\n        const node = {\n          type: 'text',\n          text,\n          marks: marks || undefined,\n        }\n\n        return node\n      },\n      createNode: (type: string, attrs?: any, content?: JSONContent[]) => {\n        const node = {\n          type,\n          attrs: attrs || undefined,\n          content: content || undefined,\n        }\n\n        if (!attrs || Object.keys(attrs).length === 0) {\n          delete node.attrs\n        }\n\n        return node\n      },\n      applyMark: (markType: string, content: JSONContent[], attrs?: any) => ({\n        mark: markType,\n        content,\n        attrs: attrs && Object.keys(attrs).length > 0 ? attrs : undefined,\n      }),\n    }\n  }\n\n  /**\n   * Escape special regex characters in a string.\n   */\n  private escapeRegex(str: string): string {\n    return str.replace(/[.*+?^${}()|[\\]\\\\]/g, '\\\\$&')\n  }\n\n  /**\n   * Parse inline tokens (bold, italic, links, etc.) into text nodes with marks.\n   * This is the complex part that handles mark nesting and boundaries.\n   */\n  private parseInlineTokens(tokens: MarkdownToken[]): JSONContent[] {\n    const result: JSONContent[] = []\n\n    // Process tokens sequentially using an index so we can lookahead and\n    // merge split inline HTML fragments like: text / <em> / inner / </em> / text\n    for (let i = 0; i < tokens.length; i += 1) {\n      const token = tokens[i]\n\n      if (token.type === 'text') {\n        result.push({\n          type: 'text',\n          text: token.text || '',\n        })\n      } else if (token.type === 'html') {\n        // Handle possible split inline HTML by attempting to detect an\n        // opening tag and searching forward for a matching closing tag.\n        const raw = (token.raw ?? token.text ?? '').toString()\n\n        // Quick checks for opening vs. closing tag\n        const isClosing = /^<\\/[\\s]*[\\w-]+/i.test(raw)\n        const openMatch = raw.match(/^<[\\s]*([\\w-]+)(\\s|>|\\/|$)/i)\n\n        if (!isClosing && openMatch && !/\\/>$/.test(raw)) {\n          // Try to find the corresponding closing html token for this tag\n          const tagName = openMatch[1]\n          const escapedTagName = this.escapeRegex(tagName)\n          const closingRegex = new RegExp(`^<\\\\/\\\\s*${escapedTagName}\\\\b`, 'i')\n          let foundIndex = -1\n\n          // Collect intermediate raw parts to reconstruct full HTML fragment\n          const parts: string[] = [raw]\n          for (let j = i + 1; j < tokens.length; j += 1) {\n            const t = tokens[j]\n            const tRaw = (t.raw ?? t.text ?? '').toString()\n            parts.push(tRaw)\n            if (t.type === 'html' && closingRegex.test(tRaw)) {\n              foundIndex = j\n              break\n            }\n          }\n\n          if (foundIndex !== -1) {\n            // Merge opening + inner + closing into one html fragment and parse\n            const mergedRaw = parts.join('')\n            const mergedToken = {\n              type: 'html',\n              raw: mergedRaw,\n              text: mergedRaw,\n              block: false,\n            } as unknown as MarkdownToken\n\n            const parsed = this.parseHTMLToken(mergedToken)\n            if (parsed) {\n              const normalized = this.normalizeParseResult(parsed as any)\n              if (Array.isArray(normalized)) {\n                result.push(...normalized)\n              } else if (normalized) {\n                result.push(normalized)\n              }\n            }\n\n            // Advance i to the closing token\n            i = foundIndex\n            continue\n          }\n        }\n\n        // Fallback: single html token parse\n        const parsedSingle = this.parseHTMLToken(token)\n        if (parsedSingle) {\n          const normalized = this.normalizeParseResult(parsedSingle as any)\n          if (Array.isArray(normalized)) {\n            result.push(...normalized)\n          } else if (normalized) {\n            result.push(normalized)\n          }\n        }\n      } else if (token.type) {\n        // Handle inline marks (bold, italic, etc.)\n        const markHandler = this.getHandlerForToken(token.type)\n        if (markHandler && markHandler.parseMarkdown) {\n          const helpers = this.createParseHelpers()\n          const parsed = markHandler.parseMarkdown(token, helpers)\n\n          if (this.isMarkResult(parsed)) {\n            // This is a mark result - apply the mark to the content\n            const markedContent = this.applyMarkToContent(parsed.mark, parsed.content, parsed.attrs)\n            result.push(...markedContent)\n          } else {\n            // Regular inline node\n            const normalized = this.normalizeParseResult(parsed)\n            if (Array.isArray(normalized)) {\n              result.push(...normalized)\n            } else if (normalized) {\n              result.push(normalized)\n            }\n          }\n        } else if (token.tokens) {\n          // Fallback: try to parse children if they exist\n          result.push(...this.parseInlineTokens(token.tokens))\n        }\n      }\n    }\n\n    return result\n  }\n\n  /**\n   * Apply a mark to content nodes.\n   */\n  private applyMarkToContent(markType: string, content: JSONContent[], attrs?: any): JSONContent[] {\n    return content.map(node => {\n      if (node.type === 'text') {\n        // Add the mark to existing marks or create new marks array\n        const existingMarks = node.marks || []\n        const newMark = attrs ? { type: markType, attrs } : { type: markType }\n        return {\n          ...node,\n          marks: [...existingMarks, newMark],\n        }\n      }\n\n      // For non-text nodes, recursively apply to content\n      return {\n        ...node,\n        content: node.content ? this.applyMarkToContent(markType, node.content, attrs) : undefined,\n      }\n    })\n  } /**\n   * Check if a parse result represents a mark to be applied.\n   */\n  private isMarkResult(result: any): result is { mark: string; content: JSONContent[]; attrs?: any } {\n    return result && typeof result === 'object' && 'mark' in result\n  }\n\n  /**\n   * Normalize parse results to ensure they're valid JSONContent.\n   */\n  private normalizeParseResult(result: MarkdownParseResult): JSONContent | JSONContent[] | null {\n    if (!result) {\n      return null\n    }\n\n    if (this.isMarkResult(result)) {\n      // This shouldn't happen at the top level, but handle it gracefully\n      return result.content\n    }\n\n    return result as JSONContent | JSONContent[]\n  }\n\n  /**\n   * Fallback parsing for common tokens when no specific handler is registered.\n   */\n  private parseFallbackToken(\n    token: MarkdownToken,\n    parseImplicitEmptyParagraphs = false,\n  ): JSONContent | JSONContent[] | null {\n    switch (token.type) {\n      case 'paragraph':\n        return {\n          type: 'paragraph',\n          content: token.tokens ? this.parseInlineTokens(token.tokens) : [],\n        }\n\n      case 'heading':\n        return {\n          type: 'heading',\n          attrs: { level: token.depth || 1 },\n          content: token.tokens ? this.parseInlineTokens(token.tokens) : [],\n        }\n\n      case 'text':\n        return {\n          type: 'text',\n          text: token.text || '',\n        }\n\n      case 'html':\n        // Parse HTML using extensions' parseHTML methods\n        return this.parseHTMLToken(token)\n\n      case 'space':\n        return null\n\n      default:\n        // Unknown token type - try to parse children if they exist\n        if (token.tokens) {\n          return this.parseTokens(token.tokens, parseImplicitEmptyParagraphs)\n        }\n        return null\n    }\n  }\n\n  /**\n   * Parse HTML tokens using extensions' parseHTML methods.\n   * This allows HTML within markdown to be parsed according to extension rules.\n   */\n  private parseHTMLToken(token: MarkdownToken): JSONContent | JSONContent[] | null {\n    const html = token.text || token.raw || ''\n\n    if (!html.trim()) {\n      return null\n    }\n\n    // Check if we're in a server-side environment (no window object)\n    // If so, fall back to treating HTML as plain text to avoid runtime errors\n    if (typeof window === 'undefined') {\n      // For block-level HTML, wrap in a paragraph to maintain valid document structure\n      if (token.block) {\n        return {\n          type: 'paragraph',\n          content: [\n            {\n              type: 'text',\n              text: html,\n            },\n          ],\n        }\n      }\n      // For inline HTML, return plain text\n      return {\n        type: 'text',\n        text: html,\n      }\n    }\n\n    // Use generateJSON to parse the HTML using extensions' parseHTML rules\n    try {\n      const parsed = generateJSON(html, this.baseExtensions)\n\n      // If the result is a doc node, extract its content\n      if (parsed.type === 'doc' && parsed.content) {\n        // For block-level HTML, return the content array\n        if (token.block) {\n          return parsed.content\n        }\n\n        // For inline HTML, we need to flatten the content appropriately\n        // If there's only one paragraph with content, unwrap it\n        if (parsed.content.length === 1 && parsed.content[0].type === 'paragraph' && parsed.content[0].content) {\n          return parsed.content[0].content\n        }\n\n        return parsed.content\n      }\n\n      return parsed as JSONContent\n    } catch (error) {\n      throw new Error(`Failed to parse HTML in markdown: ${error}`)\n    }\n  }\n\n  renderNodeToMarkdown(\n    node: JSONContent,\n    parentNode?: JSONContent,\n    index = 0,\n    level = 0,\n    meta: Record<string, any> = {},\n  ): string {\n    // if node is a text node, we simply return it's text content\n    // marks are handled at the array level in renderNodesWithMarkBoundaries\n    if (node.type === 'text') {\n      return node.text || ''\n    }\n\n    if (!node.type) {\n      return ''\n    }\n\n    const handler = this.getHandlerForToken(node.type)\n    if (!handler) {\n      return ''\n    }\n\n    const previousNode = Array.isArray(parentNode?.content) && index > 0 ? parentNode.content[index - 1] : undefined\n    const helpers: MarkdownRendererHelpers = {\n      renderChildren: (nodes, separator) => {\n        const childLevel = handler.isIndenting ? level + 1 : level\n\n        if (!Array.isArray(nodes) && (nodes as any).content) {\n          return this.renderNodes((nodes as any).content as JSONContent[], node, separator || '', index, childLevel)\n        }\n\n        return this.renderNodes(nodes, node, separator || '', index, childLevel)\n      },\n      renderChild: (childNode, childIndex) => {\n        const childLevel = handler.isIndenting ? level + 1 : level\n\n        return this.renderNodeToMarkdown(childNode, node, childIndex, childLevel)\n      },\n      indent: content => {\n        return this.indentString + content\n      },\n      wrapInBlock: wrapInMarkdownBlock,\n    }\n\n    const context: RenderContext = {\n      index,\n      level,\n      parentType: parentNode?.type,\n      previousNode,\n      meta: {\n        parentAttrs: parentNode?.attrs,\n        ...meta,\n      },\n    }\n\n    // First render the node itself (this will render children recursively)\n    const rendered = handler.renderMarkdown?.(node, helpers, context) || ''\n\n    return rendered\n  }\n\n  /**\n   * Render a node or an array of nodes. Parent type controls how children\n   * are joined (which determines newline insertion between children).\n   */\n  renderNodes(\n    nodeOrNodes: JSONContent | JSONContent[],\n    parentNode?: JSONContent,\n    separator = '',\n    index = 0,\n    level = 0,\n  ): string {\n    // if we have just one node, call renderNodeToMarkdown directly\n    if (!Array.isArray(nodeOrNodes)) {\n      if (!nodeOrNodes.type) {\n        return ''\n      }\n\n      return this.renderNodeToMarkdown(nodeOrNodes, parentNode, index, level)\n    }\n\n    return this.renderNodesWithMarkBoundaries(nodeOrNodes, parentNode, separator, level)\n  }\n\n  /**\n   * Render an array of nodes while properly tracking mark boundaries.\n   * This handles cases where marks span across multiple text nodes.\n   */\n  private renderNodesWithMarkBoundaries(\n    nodes: JSONContent[],\n    parentNode?: JSONContent,\n    separator = '',\n    level = 0,\n  ): string {\n    const result: string[] = []\n    const activeMarks: Map<string, any> = new Map()\n    const reopenWithHtmlOnNextOpen = new Set<string>()\n    const markOpeningModes = new Map<string, 'markdown' | 'html'>()\n    nodes.forEach((node, i) => {\n      // Lookahead to the next node to determine if marks need to be closed\n      const nextNode = i < nodes.length - 1 ? nodes[i + 1] : null\n\n      if (!node.type) {\n        return\n      }\n\n      if (node.type === 'text') {\n        let textContent = node.text || ''\n        const currentMarks = new Map((node.marks || []).map(mark => [mark.type, mark]))\n\n        // Find marks that need to be closed and opened\n        const marksToOpen = findMarksToOpen(activeMarks, currentMarks)\n        const marksToClose = findMarksToClose(currentMarks, nextNode)\n\n        // When marks simultaneously close (old) AND open (new) at this boundary, the naive\n        // approach of appending old-close and prepending new-open produces interleaved\n        // delimiters like `*456**` (italic open, text, bold close) instead of properly\n        // nested `_456_**` (italic open, text, italic close, bold close).\n        //\n        // The fix: when both are present, defer old mark closings to the end of the node\n        // (after the new marks also close), ensuring correct inner-before-outer order.\n        //\n        // If an already-active mark ends on this node while another mark opens on this same\n        // node, we defer closing the active mark until the end of the node so nesting stays\n        // valid (`**...++abc++**` instead of `**...++abc**++`).\n        const activeMarksClosingHere = marksToClose.filter(markType => activeMarks.has(markType))\n        const hasCrossedBoundary = activeMarksClosingHere.length > 0 && marksToOpen.length > 0\n\n        let middleTrailingWhitespace = ''\n\n        if (marksToClose.length > 0 && !hasCrossedBoundary) {\n          // Extract trailing whitespace before closing marks to prevent invalid markdown like \"**text **\"\n          const middleTrailingMatch = textContent.match(/(\\s+)$/)\n          if (middleTrailingMatch) {\n            middleTrailingWhitespace = middleTrailingMatch[1]\n            textContent = textContent.slice(0, -middleTrailingWhitespace.length)\n          }\n        }\n\n        if (!hasCrossedBoundary) {\n          // Normal path: close marks that are ending here (no new marks opening simultaneously)\n          marksToClose.forEach(markType => {\n            if (!activeMarks.has(markType)) {\n              return\n            }\n\n            const mark = currentMarks.get(markType)\n            const closeMarkdown = this.getMarkClosing(markType, mark, markOpeningModes.get(markType))\n            if (closeMarkdown) {\n              textContent += closeMarkdown\n            }\n            if (activeMarks.has(markType)) {\n              activeMarks.delete(markType)\n              markOpeningModes.delete(markType)\n            }\n          })\n        }\n\n        // Open new marks (should be at the beginning)\n        // Extract leading whitespace before opening marks to prevent invalid markdown like \"** text**\"\n        let leadingWhitespace = ''\n        if (marksToOpen.length > 0) {\n          const leadingMatch = textContent.match(/^(\\s+)/)\n          if (leadingMatch) {\n            leadingWhitespace = leadingMatch[1]\n            textContent = textContent.slice(leadingWhitespace.length)\n          }\n        }\n\n        // Snapshot active mark types before opening new marks, so each new mark's delimiter\n        // is chosen based on what is already active (not including itself).\n        // When crossing a boundary, old marks are still in activeMarks here (not yet removed),\n        // so new marks correctly see them as active context.\n        marksToOpen.forEach(({ type, mark }) => {\n          const openingMode = reopenWithHtmlOnNextOpen.has(type) ? 'html' : 'markdown'\n          const openMarkdown = this.getMarkOpening(type, mark, openingMode)\n          if (openMarkdown) {\n            textContent = openMarkdown + textContent\n          }\n          markOpeningModes.set(type, openingMode)\n          reopenWithHtmlOnNextOpen.delete(type)\n        })\n\n        if (!hasCrossedBoundary) {\n          marksToOpen\n            .slice()\n            .reverse()\n            .forEach(({ type, mark }) => {\n              activeMarks.set(type, mark)\n            })\n        }\n\n        // Add leading whitespace before the mark opening\n        textContent = leadingWhitespace + textContent\n\n        // Determine marks to close at the end of this node.\n        // On a crossed boundary, we close new marks (inner) first, then old marks (outer),\n        // ensuring correct nesting order. Both sets are removed from activeMarks so the\n        // next node's marksToOpen will reopen whichever ones continue.\n        let marksToCloseAtEnd: string[]\n        if (hasCrossedBoundary) {\n          const nextMarkTypes = new Set((nextNode?.marks || []).map((mark: any) => mark.type))\n\n          marksToOpen.forEach(({ type }) => {\n            if (nextMarkTypes.has(type) && this.getHtmlReopenTags(type)) {\n              reopenWithHtmlOnNextOpen.add(type)\n            }\n          })\n\n          marksToCloseAtEnd = [\n            ...marksToOpen.map(m => m.type), // inner (opened here) — close first\n            ...activeMarksClosingHere, // outer (were active before) — close last\n          ]\n        } else {\n          marksToCloseAtEnd = findMarksToCloseAtEnd(activeMarks, currentMarks, nextNode, this.markSetsEqual.bind(this))\n        }\n\n        // Extract trailing whitespace before closing marks to prevent invalid markdown like \"**text **\"\n        let trailingWhitespace = ''\n        if (marksToCloseAtEnd.length > 0) {\n          const trailingMatch = textContent.match(/(\\s+)$/)\n          if (trailingMatch) {\n            trailingWhitespace = trailingMatch[1]\n            textContent = textContent.slice(0, -trailingWhitespace.length)\n          }\n        }\n\n        marksToCloseAtEnd.forEach(markType => {\n          const mark = activeMarks.get(markType) ?? currentMarks.get(markType)\n          const closeMarkdown = this.getMarkClosing(markType, mark, markOpeningModes.get(markType))\n          if (closeMarkdown) {\n            textContent += closeMarkdown\n          }\n          activeMarks.delete(markType)\n          markOpeningModes.delete(markType)\n        })\n\n        // Add trailing whitespace after the mark closing\n        textContent += trailingWhitespace\n        textContent += middleTrailingWhitespace\n\n        result.push(textContent)\n      } else {\n        // For non-text nodes, close all active marks before rendering, then reopen after\n        const marksToReopen = new Map(activeMarks)\n        const openingModesToReopen = new Map(markOpeningModes)\n\n        // Close all marks before the node\n        const beforeMarkdown = closeMarksBeforeNode(activeMarks, (markType, mark) => {\n          return this.getMarkClosing(markType, mark, markOpeningModes.get(markType))\n        })\n        markOpeningModes.clear()\n\n        // Render the node\n        const nodeContent = this.renderNodeToMarkdown(node, parentNode, i, level)\n\n        // Reopen marks after the node, but NOT after a hard break\n        // Hard breaks should terminate marks (they create a line break where marks don't continue)\n        const afterMarkdown =\n          node.type === 'hardBreak'\n            ? ''\n            : reopenMarksAfterNode(marksToReopen, activeMarks, (markType, mark) => {\n                const openingMode = openingModesToReopen.get(markType) ?? 'markdown'\n                markOpeningModes.set(markType, openingMode)\n                return this.getMarkOpening(markType, mark, openingMode)\n              })\n\n        result.push(beforeMarkdown + nodeContent + afterMarkdown)\n      }\n    })\n\n    return result.join(separator)\n  }\n\n  /**\n   * Get the opening markdown syntax for a mark type.\n   */\n  private getMarkOpening(markType: string, mark: any, openingMode: 'markdown' | 'html' = 'markdown'): string {\n    if (openingMode === 'html') {\n      return this.getHtmlReopenTags(markType)?.open || ''\n    }\n\n    const handlers = this.getHandlersForNodeType(markType)\n    const handler = handlers.length > 0 ? handlers[0] : undefined\n    if (!handler || !handler.renderMarkdown) {\n      return ''\n    }\n\n    // Use a unique placeholder that's extremely unlikely to appear in real content\n    const placeholder = '\\uE000__TIPTAP_MARKDOWN_PLACEHOLDER__\\uE001'\n\n    // For most marks, we can extract the opening syntax by rendering a simple case\n    const syntheticNode: JSONContent = {\n      type: markType,\n      attrs: mark.attrs || {},\n      content: [{ type: 'text', text: placeholder }],\n    }\n\n    try {\n      const rendered = handler.renderMarkdown(\n        syntheticNode,\n        {\n          renderChildren: () => placeholder,\n          renderChild: () => placeholder,\n          indent: (content: string) => content,\n          wrapInBlock: (prefix: string, content: string) => prefix + content,\n        },\n        { index: 0, level: 0, parentType: 'text', meta: {} },\n      )\n\n      // Extract the opening part (everything before placeholder)\n      const placeholderIndex = rendered.indexOf(placeholder)\n      return placeholderIndex >= 0 ? rendered.substring(0, placeholderIndex) : ''\n    } catch (err) {\n      throw new Error(`Failed to get mark opening for ${markType}: ${err}`)\n    }\n  }\n\n  /**\n   * Get the closing markdown syntax for a mark type.\n   */\n  private getMarkClosing(markType: string, mark: any, openingMode: 'markdown' | 'html' = 'markdown'): string {\n    if (openingMode === 'html') {\n      return this.getHtmlReopenTags(markType)?.close || ''\n    }\n\n    const handlers = this.getHandlersForNodeType(markType)\n    const handler = handlers.length > 0 ? handlers[0] : undefined\n    if (!handler || !handler.renderMarkdown) {\n      return ''\n    }\n\n    // Use a unique placeholder that's extremely unlikely to appear in real content\n    const placeholder = '\\uE000__TIPTAP_MARKDOWN_PLACEHOLDER__\\uE001'\n\n    const syntheticNode: JSONContent = {\n      type: markType,\n      attrs: mark.attrs || {},\n      content: [{ type: 'text', text: placeholder }],\n    }\n\n    try {\n      const rendered = handler.renderMarkdown(\n        syntheticNode,\n        {\n          renderChildren: () => placeholder,\n          renderChild: () => placeholder,\n          indent: (content: string) => content,\n          wrapInBlock: (prefix: string, content: string) => prefix + content,\n        },\n        { index: 0, level: 0, parentType: 'text', meta: {} },\n      )\n\n      // Extract the closing part (everything after placeholder)\n      const placeholderIndex = rendered.indexOf(placeholder)\n      const placeholderEnd = placeholderIndex + placeholder.length\n      return placeholderIndex >= 0 ? rendered.substring(placeholderEnd) : ''\n    } catch (err) {\n      throw new Error(`Failed to get mark closing for ${markType}: ${err}`)\n    }\n  }\n\n  /**\n   * Returns the inline HTML tags an extension exposes for overlap-boundary\n   * reopen handling, if that mark explicitly opted into HTML reopen mode.\n   */\n  private getHtmlReopenTags(markType: string): { open: string; close: string } | undefined {\n    const handlers = this.getHandlersForNodeType(markType)\n    const handler = handlers.length > 0 ? handlers[0] : undefined\n\n    return handler?.htmlReopen\n  }\n\n  /**\n   * Check if two mark sets are equal.\n   */\n  private markSetsEqual(marks1: Map<string, any>, marks2: Map<string, any>): boolean {\n    if (marks1.size !== marks2.size) {\n      return false\n    }\n\n    return Array.from(marks1.keys()).every(type => marks2.has(type))\n  }\n}\n\nexport default MarkdownManager\n","import type { Content, MarkdownToken } from '@tiptap/core'\nimport type { Fragment, Node } from '@tiptap/pm/model'\n\nimport type { ContentType } from './types.js'\n\n/**\n * Wraps each line of the content with the given prefix.\n * @param prefix The prefix to wrap each line with.\n * @param content The content to wrap.\n * @returns The content with each line wrapped with the prefix.\n */\nexport function wrapInMarkdownBlock(prefix: string, content: string) {\n  // split content lines\n  const lines = content.split('\\n')\n\n  // add empty strings between every line\n  const output = lines\n    // add empty lines between each block\n    .flatMap(line => [line, ''])\n    // add the prefix to each line\n    .map(line => 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nextNode.marks) {\n      const nextMarks = new Map(nextNode.marks.map((mark: any) => [mark.type, mark]))\n      Array.from(activeMarks.keys())\n        .reverse()\n        .forEach(markType => {\n          if (!nextMarks.has(markType)) {\n            marksToCloseAtEnd.push(markType)\n          }\n        })\n    } else if (isLastNode || nextNodeHasNoMarks) {\n      // Close all active marks\n      marksToCloseAtEnd.push(...Array.from(activeMarks.keys()).reverse())\n    }\n  }\n\n  return marksToCloseAtEnd\n}\n\n/**\n * Closes active marks before rendering a non-text node.\n * Returns the closing markdown syntax and clears the active marks.\n */\nexport function closeMarksBeforeNode(\n  activeMarks: Map<string, any>,\n  getMarkClosing: (markType: string, mark: any) => string,\n): string {\n  let beforeMarkdown = ''\n  Array.from(activeMarks.keys())\n    .reverse()\n    .forEach(markType => {\n      const mark = activeMarks.get(markType)\n      const closeMarkdown = 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+{"version":3,"sources":["../src/Extension.ts","../src/MarkdownManager.ts","../src/utils.ts"],"sourcesContent":["import {\n  type InsertContentAtOptions as MarkdownInsertContentAtOptions,\n  type InsertContentOptions as MarkdownInsertContentOptions,\n  type SetContentOptions as MarkdownSetContentOptions,\n  commands,\n  Extension,\n} from '@tiptap/core'\nimport type { marked } from 'marked'\n\nimport MarkdownManager from './MarkdownManager.js'\nimport type { ContentType } from './types.js'\nimport { assumeContentType } from './utils.js'\n\ndeclare module '@tiptap/core' {\n  interface Editor {\n    /**\n     * Get the content of the editor as markdown.\n     */\n    getMarkdown: () => string\n\n    /**\n     * The markdown manager instance.\n     */\n    markdown?: MarkdownManager\n  }\n\n  interface EditorOptions {\n    /**\n     * The content type the content is provided as.\n     *\n     * @default 'json'\n     */\n    contentType?: ContentType\n  }\n\n  interface Storage {\n    markdown: MarkdownExtensionStorage\n  }\n\n  interface InsertContentOptions {\n    /**\n     * The content type the content is provided as.\n     *\n     * @default 'json'\n     */\n    contentType?: ContentType\n  }\n\n  interface InsertContentAtOptions {\n    /**\n     * The content type the content is provided as.\n     *\n     * @default 'json'\n     */\n    contentType?: ContentType\n  }\n\n  interface SetContentOptions {\n    /**\n     * The content type the content is provided as.\n     *\n     * @default 'json'\n     */\n    contentType?: ContentType\n  }\n}\n\nexport type MarkdownExtensionOptions = {\n  /**\n   * Configure the indentation style and size for lists and code blocks.\n   * - `style`: Choose between spaces or tabs. Default is 'space'.\n   * - `size`: Number of spaces or tabs for indentation. Default is 2.\n   */\n  indentation?: { style?: 'space' | 'tab'; size?: number }\n\n  /**\n   * Use a custom version of `marked` for markdown parsing and serialization.\n   * If not provided, the default `marked` instance will be used.\n   */\n  marked?: typeof marked\n\n  /**\n   * Options to pass to `marked.setOptions()`.\n   * See the [marked documentation](https://marked.js.org/using_advanced#options) for available options.\n   */\n  markedOptions?: Parameters<typeof marked.setOptions>[0]\n}\n\nexport type MarkdownExtensionStorage = {\n  manager: MarkdownManager\n}\n\nexport const Markdown = Extension.create<MarkdownExtensionOptions, MarkdownExtensionStorage>({\n  name: 'markdown',\n\n  addOptions() {\n    return {\n      indentation: { style: 'space', size: 2 },\n      marked: undefined,\n      markedOptions: {},\n    }\n  },\n\n  addCommands() {\n    return {\n      setContent: (content, options?: MarkdownSetContentOptions) => {\n        // if no contentType is specified, we assume the content is in JSON format OR HTML format\n        if (!options?.contentType) {\n          return commands.setContent(content, options)\n        }\n\n        const actualContentType = assumeContentType(content, options?.contentType)\n\n        if (actualContentType !== 'markdown' || !this.editor.markdown) {\n          return commands.setContent(content, options)\n        }\n\n        const mdContent = this.editor.markdown.parse(content as string)\n        return commands.setContent(mdContent, options)\n      },\n\n      insertContent: (value, options?: MarkdownInsertContentOptions) => {\n        // if no contentType is specified, we assume the content is in JSON format OR HTML format\n        if (!options?.contentType) {\n          return commands.insertContent(value, options)\n        }\n\n        const actualContentType = assumeContentType(value, options?.contentType)\n\n        if (actualContentType !== 'markdown' || !this.editor.markdown) {\n          return commands.insertContent(value, options)\n        }\n\n        const mdContent = this.editor.markdown.parse(value as string)\n        return commands.insertContent(mdContent, options)\n      },\n\n      insertContentAt: (position, value, options?: MarkdownInsertContentAtOptions) => {\n        // if no contentType is specified, we assume the content is in JSON format OR HTML format\n        if (!options?.contentType) {\n          return commands.insertContentAt(position, value, options)\n        }\n\n        const actualContentType = assumeContentType(value, options?.contentType)\n\n        if (actualContentType !== 'markdown' || !this.editor.markdown) {\n          return commands.insertContentAt(position, value, options)\n        }\n\n        const mdContent = this.editor.markdown.parse(value as string)\n        return commands.insertContentAt(position, mdContent, options)\n      },\n    }\n  },\n\n  addStorage() {\n    return {\n      manager: new MarkdownManager({\n        indentation: this.options.indentation,\n        marked: this.options.marked,\n        markedOptions: this.options.markedOptions,\n        extensions: [],\n      }),\n    }\n  },\n\n  onBeforeCreate() {\n    if (this.editor.markdown) {\n      console.error(\n        '[tiptap][markdown]: There is already a `markdown` property on the editor instance. This might lead to unexpected behavior.',\n      )\n      return\n    }\n\n    this.storage.manager = new MarkdownManager({\n      indentation: this.options.indentation,\n      marked: this.options.marked,\n      markedOptions: this.options.markedOptions,\n      extensions: this.editor.extensionManager.baseExtensions,\n    })\n\n    this.editor.markdown = this.storage.manager\n\n    // add a `getMarkdown()` method to the editor\n    this.editor.getMarkdown = () => {\n      return this.storage.manager.serialize(this.editor.getJSON())\n    }\n\n    if (!this.editor.options.contentType) {\n      return\n    }\n\n    const assumedType = assumeContentType(this.editor.options.content, this.editor.options.contentType)\n    if (assumedType !== 'markdown') {\n      return\n    }\n\n    if (!this.editor.markdown) {\n      throw new Error(\n        '[tiptap][markdown]: The `contentType` option is set to \"markdown\", but the Markdown extension is not added to the editor. Please add the Markdown extension to use this feature.',\n      )\n    }\n\n    if (this.editor.options.content === undefined || typeof this.editor.options.content !== 'string') {\n      throw new Error(\n        '[tiptap][markdown]: The `contentType` option is set to \"markdown\", but the initial content is not a string. Please provide the initial content as a markdown string.',\n      )\n    }\n\n    const json = this.editor.markdown.parse(this.editor.options.content as string)\n    this.editor.options.content = json\n  },\n})\n","import {\n  type AnyExtension,\n  type ExtendableConfig,\n  type JSONContent,\n  type MarkdownExtensionSpec,\n  type MarkdownLexerConfiguration,\n  type MarkdownParseHelpers,\n  type MarkdownParseResult,\n  type MarkdownRendererHelpers,\n  type MarkdownToken,\n  type MarkdownTokenizer,\n  type RenderContext,\n  flattenExtensions,\n  generateJSON,\n  getExtensionField,\n} from '@tiptap/core'\nimport { type Lexer, type Token, type TokenizerExtension, type TokenizerThis, marked } from 'marked'\n\nimport {\n  closeMarksBeforeNode,\n  findMarksToClose,\n  findMarksToCloseAtEnd,\n  findMarksToOpen,\n  isTaskItem,\n  reopenMarksAfterNode,\n  wrapInMarkdownBlock,\n} from './utils.js'\n\nexport class MarkdownManager {\n  private markedInstance: typeof marked\n  private activeParseLexer: Lexer | null = null\n  private registry: Map<string, MarkdownExtensionSpec[]>\n  private nodeTypeRegistry: Map<string, MarkdownExtensionSpec[]>\n  private indentStyle: 'space' | 'tab'\n  private indentSize: number\n  private baseExtensions: AnyExtension[] = []\n  private extensions: AnyExtension[] = []\n\n  /**\n   * Create a MarkdownManager.\n   * @param options.marked Optional marked instance to use (injected).\n   * @param options.markedOptions Optional options to pass to marked.setOptions\n   * @param options.indentation Indentation settings (style and size).\n   * @param options.extensions An array of Tiptap extensions to register for markdown parsing and rendering.\n   */\n  constructor(options?: {\n    marked?: typeof marked\n    markedOptions?: Parameters<typeof marked.setOptions>[0]\n    indentation?: { style?: 'space' | 'tab'; size?: number }\n    extensions: AnyExtension[]\n  }) {\n    this.markedInstance = options?.marked ?? marked\n    this.indentStyle = options?.indentation?.style ?? 'space'\n    this.indentSize = options?.indentation?.size ?? 2\n    this.baseExtensions = options?.extensions || []\n\n    if (options?.markedOptions && typeof this.markedInstance.setOptions === 'function') {\n      this.markedInstance.setOptions(options.markedOptions)\n    }\n\n    this.registry = new Map()\n    this.nodeTypeRegistry = new Map()\n\n    // If extensions were provided, register them now\n    if (options?.extensions) {\n      this.baseExtensions = options.extensions\n      const flattened = flattenExtensions(options.extensions)\n      flattened.forEach(ext => this.registerExtension(ext))\n    }\n  }\n\n  /** Returns the underlying marked instance. */\n  get instance(): typeof marked {\n    return this.markedInstance\n  }\n\n  /** Returns the correct indentCharacter (space or tab) */\n  get indentCharacter(): string {\n    return this.indentStyle === 'space' ? ' ' : '\\t'\n  }\n\n  /** Returns the correct indentString repeated X times */\n  get indentString(): string {\n    return this.indentCharacter.repeat(this.indentSize)\n  }\n\n  /** Helper to quickly check whether a marked instance is available. */\n  hasMarked(): boolean {\n    return !!this.markedInstance\n  }\n\n  /**\n   * Register a Tiptap extension (Node/Mark/Extension). This will read\n   * `markdownName`, `parseMarkdown`, `renderMarkdown` and `priority` from the\n   * extension config (using the same resolution used across the codebase).\n   */\n  registerExtension(extension: AnyExtension): void {\n    // Keep track of all extensions for HTML parsing\n    this.extensions.push(extension)\n\n    const name = extension.name\n    const tokenName =\n      (getExtensionField(extension, 'markdownTokenName') as ExtendableConfig['markdownTokenName']) || name\n    const parseMarkdown = getExtensionField(extension, 'parseMarkdown') as ExtendableConfig['parseMarkdown'] | undefined\n    const renderMarkdown = getExtensionField(extension, 'renderMarkdown') as\n      | ExtendableConfig['renderMarkdown']\n      | undefined\n    const tokenizer = getExtensionField(extension, 'markdownTokenizer') as\n      | ExtendableConfig['markdownTokenizer']\n      | undefined\n\n    // Read the `markdown` object from the extension config. This allows\n    // extensions to provide `markdown: { name?, parseName?, renderName?, parse?, render?, match? }`.\n    const markdownCfg = (getExtensionField(extension, 'markdownOptions') ?? null) as ExtendableConfig['markdownOptions']\n    const isIndenting = markdownCfg?.indentsContent ?? false\n    const htmlReopen = markdownCfg?.htmlReopen\n\n    const spec: MarkdownExtensionSpec = {\n      tokenName,\n      nodeName: name,\n      parseMarkdown,\n      renderMarkdown,\n      isIndenting,\n      htmlReopen,\n      tokenizer,\n    }\n\n    // Add to parse registry using parseName\n    if (tokenName && parseMarkdown) {\n      const parseExisting = this.registry.get(tokenName) || []\n      parseExisting.push(spec)\n      this.registry.set(tokenName, parseExisting)\n    }\n\n    // Add to render registry using renderName (node type)\n    if (renderMarkdown) {\n      const renderExisting = this.nodeTypeRegistry.get(name) || []\n      renderExisting.push(spec)\n      this.nodeTypeRegistry.set(name, renderExisting)\n    }\n\n    // Register custom tokenizer with marked.js\n    if (tokenizer && this.hasMarked()) {\n      this.registerTokenizer(tokenizer)\n    }\n  }\n\n  private createLexer(): Lexer {\n    return new this.markedInstance.Lexer()\n  }\n\n  private createTokenizerHelpers(lexer: Lexer): MarkdownLexerConfiguration {\n    return {\n      inlineTokens: (src: string) => lexer.inlineTokens(src),\n      blockTokens: (src: string) => lexer.blockTokens(src),\n    }\n  }\n\n  private tokenizeInline(src: string): MarkdownToken[] {\n    return (this.activeParseLexer ?? this.createLexer()).inlineTokens(src) as MarkdownToken[]\n  }\n\n  /**\n   * Register a custom tokenizer with marked.js for parsing non-standard markdown syntax.\n   */\n  private registerTokenizer(tokenizer: MarkdownTokenizer): void {\n    if (!this.hasMarked()) {\n      return\n    }\n\n    const { name, start, level = 'inline', tokenize } = tokenizer\n    const createTokenizerHelpers = this.createTokenizerHelpers.bind(this)\n    const createLexer = this.createLexer.bind(this)\n\n    let startCb: (src: string) => number\n\n    if (!start) {\n      startCb = (src: string) => {\n        // For other tokenizers, try to find a match and return its position\n        const result = tokenize(src, [], this.createTokenizerHelpers(this.createLexer()))\n        if (result && result.raw) {\n          const index = src.indexOf(result.raw)\n          return index\n        }\n        return -1\n      }\n    } else {\n      startCb = typeof start === 'function' ? start : (src: string) => src.indexOf(start)\n    }\n\n    // Create marked.js extension with proper types\n    const markedExtension: TokenizerExtension = {\n      name,\n      level,\n      start: startCb,\n      tokenizer(this: TokenizerThis, src, tokens) {\n        const helper = this.lexer ? createTokenizerHelpers(this.lexer) : createTokenizerHelpers(createLexer())\n        const result = tokenize(src, tokens, helper)\n\n        if (result && result.type) {\n          return {\n            ...result,\n            type: result.type || name,\n            raw: result.raw || '',\n            tokens: (result.tokens || []) as Token[],\n          }\n        }\n\n        return undefined\n      },\n      childTokens: [],\n    }\n\n    // Register with marked.js - use extensions array to control priority\n    this.markedInstance.use({\n      extensions: [markedExtension],\n    })\n  }\n\n  /** Get registered handlers for a token type and try each until one succeeds. */\n  private getHandlersForToken(type: string): MarkdownExtensionSpec[] {\n    try {\n      return this.registry.get(type) || []\n    } catch {\n      return []\n    }\n  }\n\n  /** Get the first handler for a token type (for backwards compatibility). */\n  private getHandlerForToken(type: string): MarkdownExtensionSpec | undefined {\n    // First try the markdown token registry (for parsing)\n    const markdownHandlers = this.getHandlersForToken(type)\n    if (markdownHandlers.length > 0) {\n      return markdownHandlers[0]\n    }\n\n    // Then try the node type registry (for rendering)\n    const nodeTypeHandlers = this.getHandlersForNodeType(type)\n    return nodeTypeHandlers.length > 0 ? nodeTypeHandlers[0] : undefined\n  }\n\n  /** Get registered handlers for a node type (for rendering). */\n  private getHandlersForNodeType(type: string): MarkdownExtensionSpec[] {\n    try {\n      return this.nodeTypeRegistry.get(type) || []\n    } catch {\n      return []\n    }\n  }\n\n  /**\n   * Serialize a ProseMirror-like JSON document (or node array) to a Markdown string\n   * using registered renderers and fallback renderers.\n   */\n  serialize(docOrContent: JSONContent): string {\n    if (!docOrContent) {\n      return ''\n    }\n\n    const result = this.renderNodes(docOrContent, docOrContent)\n    // Return empty string if result is only whitespace entities or non-breaking spaces\n    return this.isEmptyOutput(result) ? '' : result\n  }\n\n  /**\n   * Check if the markdown output represents an empty document.\n   * Empty documents may contain only &nbsp; entities or non-breaking space characters\n   * which are used by the Paragraph extension to preserve blank lines.\n   */\n  private isEmptyOutput(markdown: string): boolean {\n    if (!markdown || markdown.trim() === '') {\n      return true\n    }\n\n    // Check if the output is only &nbsp; entities or non-breaking space characters\n    const cleanedOutput = markdown\n      .replace(/&nbsp;/g, '')\n      .replace(/\\u00A0/g, '')\n      .trim()\n    return cleanedOutput === ''\n  }\n\n  /**\n   * Parse markdown string into Tiptap JSON document using registered extension handlers.\n   */\n  parse(markdown: string): JSONContent {\n    if (!this.hasMarked()) {\n      throw new Error('No marked instance available for parsing')\n    }\n\n    const previousParseLexer = this.activeParseLexer\n    const parseLexer = this.createLexer()\n\n    this.activeParseLexer = parseLexer\n\n    try {\n      // Use a parse-scoped lexer so follow-up inline tokenization can reuse\n      // the same configured lexer state without sharing it across parses.\n      const tokens = parseLexer.lex(markdown) as MarkdownToken[]\n\n      // Convert tokens to Tiptap JSON\n      const content = this.parseTokens(tokens, true)\n\n      // Return a document node containing the parsed content\n      return {\n        type: 'doc',\n        content,\n      }\n    } finally {\n      this.activeParseLexer = previousParseLexer\n    }\n  }\n\n  /**\n   * Convert an array of marked tokens into Tiptap JSON nodes using registered extension handlers.\n   */\n  private parseTokens(tokens: MarkdownToken[], parseImplicitEmptyParagraphs = false): JSONContent[] {\n    const nonSpaceTokenIndexes = tokens.reduce<number[]>((indexes, token, index) => {\n      if (token.type !== 'space') {\n        indexes.push(index)\n      }\n\n      return indexes\n    }, [])\n\n    let previousNonSpaceTokenIndex = -1\n    let nextNonSpaceTokenPointer = 0\n\n    return tokens.flatMap((token, index) => {\n      while (\n        nextNonSpaceTokenPointer < nonSpaceTokenIndexes.length &&\n        nonSpaceTokenIndexes[nextNonSpaceTokenPointer] < index\n      ) {\n        previousNonSpaceTokenIndex = nonSpaceTokenIndexes[nextNonSpaceTokenPointer]\n        nextNonSpaceTokenPointer += 1\n      }\n\n      if (parseImplicitEmptyParagraphs && token.type === 'space') {\n        const nextNonSpaceTokenIndex = nonSpaceTokenIndexes[nextNonSpaceTokenPointer] ?? -1\n\n        return this.createImplicitEmptyParagraphsFromSpace(token, previousNonSpaceTokenIndex, nextNonSpaceTokenIndex)\n      }\n\n      const parsed = this.parseToken(token, parseImplicitEmptyParagraphs)\n\n      if (parsed === null) {\n        return []\n      }\n\n      return Array.isArray(parsed) ? parsed : [parsed]\n    })\n  }\n\n  private createImplicitEmptyParagraphsFromSpace(\n    token: MarkdownToken,\n    previousNonSpaceTokenIndex: number,\n    nextNonSpaceTokenIndex: number,\n  ): JSONContent[] {\n    const separatorCount = this.countParagraphSeparators(token.raw || '')\n\n    if (separatorCount === 0) {\n      return []\n    }\n\n    const isBoundarySpace = previousNonSpaceTokenIndex === -1 || nextNonSpaceTokenIndex === -1\n    const emptyParagraphCount = Math.max(separatorCount - (isBoundarySpace ? 0 : 1), 0)\n\n    return Array.from({ length: emptyParagraphCount }, () => ({ type: 'paragraph', content: [] }))\n  }\n\n  private countParagraphSeparators(raw: string): number {\n    return (raw.replace(/\\r\\n/g, '\\n').match(/\\n\\n/g) || []).length\n  }\n\n  /**\n   * Parse a single token into Tiptap JSON using the appropriate registered handler.\n   */\n  private parseToken(token: MarkdownToken, parseImplicitEmptyParagraphs = false): JSONContent | JSONContent[] | null {\n    if (!token.type) {\n      return null\n    }\n\n    // Special handling for 'list' tokens that may contain mixed bullet/task items\n    if (token.type === 'list') {\n      return this.parseListToken(token)\n    }\n\n    const handlers = this.getHandlersForToken(token.type)\n    const helpers = this.createParseHelpers()\n\n    // Try each handler until one returns a valid result\n    const result = handlers.find(handler => {\n      if (!handler.parseMarkdown) {\n        return false\n      }\n\n      const parseResult = handler.parseMarkdown(token, helpers)\n      const normalized = this.normalizeParseResult(parseResult)\n\n      // Check if this handler returned a valid result (not null/empty array)\n      if (normalized && (!Array.isArray(normalized) || normalized.length > 0)) {\n        // Store result for return\n        this.lastParseResult = normalized\n        return true\n      }\n\n      return false\n    })\n\n    // If a handler worked, return its result\n    if (result && this.lastParseResult) {\n      const toReturn = this.lastParseResult\n      this.lastParseResult = null // Clean up\n      return toReturn\n    }\n\n    // If no handler worked, try fallback parsing\n    return this.parseFallbackToken(token, parseImplicitEmptyParagraphs)\n  }\n\n  private lastParseResult: JSONContent | JSONContent[] | null = null\n\n  /**\n   * Parse a list token, handling mixed bullet and task list items by splitting them into separate lists.\n   * This ensures that consecutive task items and bullet items are grouped and parsed as separate list nodes.\n   *\n   * @param token The list token to parse\n   * @returns Array of parsed list nodes, or null if parsing fails\n   */\n  private parseListToken(token: MarkdownToken): JSONContent | JSONContent[] | null {\n    if (!token.items || token.items.length === 0) {\n      // No items, parse normally\n      return this.parseTokenWithHandlers(token)\n    }\n\n    const hasTask = token.items.some(item => isTaskItem(item).isTask)\n    const hasNonTask = token.items.some(item => !isTaskItem(item).isTask)\n\n    if (!hasTask || !hasNonTask || this.getHandlersForToken('taskList').length === 0) {\n      // Not mixed or no taskList extension, parse normally\n      return this.parseTokenWithHandlers(token)\n    }\n\n    // Mixed list with taskList extension available: split into separate lists\n    type TaskListItemToken = MarkdownToken & { type: 'taskItem'; checked?: boolean; indentLevel?: number }\n    const groups: { type: 'list' | 'taskList'; items: (MarkdownToken | TaskListItemToken)[] }[] = []\n    let currentGroup: (MarkdownToken | TaskListItemToken)[] = []\n    let currentType: 'list' | 'taskList' | null = null\n\n    for (let i = 0; i < token.items.length; i += 1) {\n      const item = token.items[i]\n      const { isTask, checked, indentLevel } = isTaskItem(item)\n      let processedItem = item\n\n      if (isTask) {\n        // Transform list_item into taskItem token\n        const raw = item.raw || item.text || ''\n\n        // Split raw content by lines to separate main content from nested\n        const lines = raw.split('\\n')\n\n        // Extract main content from the first line\n        const firstLineMatch = lines[0].match(/^\\s*[-+*]\\s+\\[([ xX])\\]\\s+(.*)$/)\n        const mainContent = firstLineMatch ? firstLineMatch[2] : ''\n\n        // Parse nested content from remaining lines\n        let nestedTokens: MarkdownToken[] = []\n        if (lines.length > 1) {\n          // Join all lines after the first\n          const nestedRaw = lines.slice(1).join('\\n')\n\n          // Only parse if there's actual content\n          if (nestedRaw.trim()) {\n            // Find minimum indentation of non-empty lines\n            const nestedLines = lines.slice(1)\n            const nonEmptyLines = nestedLines.filter(line => line.trim())\n            if (nonEmptyLines.length > 0) {\n              const minIndent = Math.min(...nonEmptyLines.map(line => line.length - line.trimStart().length))\n              // Remove common indentation while preserving structure\n              const trimmedLines = nestedLines.map(line => {\n                if (!line.trim()) {\n                  return '' // Keep empty lines\n                }\n                return line.slice(minIndent)\n              })\n              const nestedContent = trimmedLines.join('\\n').trim()\n              // Use the lexer to parse nested content\n              if (nestedContent) {\n                // Use the full lexer pipeline to ensure inline tokens are populated\n                nestedTokens = this.markedInstance.lexer(`${nestedContent}\\n`)\n              }\n            }\n          }\n        }\n\n        processedItem = {\n          type: 'taskItem',\n          raw: '',\n          mainContent,\n          indentLevel,\n          checked: checked ?? false,\n          text: mainContent,\n          tokens: this.tokenizeInline(mainContent),\n          nestedTokens,\n        }\n      }\n\n      const itemType: 'list' | 'taskList' = isTask ? 'taskList' : 'list'\n\n      if (currentType !== itemType) {\n        if (currentGroup.length > 0) {\n          groups.push({ type: currentType!, items: currentGroup })\n        }\n        currentGroup = [processedItem]\n        currentType = itemType\n      } else {\n        currentGroup.push(processedItem)\n      }\n    }\n\n    if (currentGroup.length > 0) {\n      groups.push({ type: currentType!, items: currentGroup })\n    }\n\n    // Parse each group as a separate token\n    const results: JSONContent[] = []\n    for (let i = 0; i < groups.length; i += 1) {\n      const group = groups[i]\n      const subToken = { ...token, type: group.type, items: group.items }\n      const parsed = this.parseToken(subToken)\n      if (parsed) {\n        if (Array.isArray(parsed)) {\n          results.push(...parsed)\n        } else {\n          results.push(parsed)\n        }\n      }\n    }\n\n    return results.length > 0 ? results : null\n  }\n\n  /**\n   * Parse a token using registered handlers (extracted for reuse).\n   */\n  private parseTokenWithHandlers(token: MarkdownToken): JSONContent | JSONContent[] | null {\n    if (!token.type) {\n      return null\n    }\n\n    const handlers = this.getHandlersForToken(token.type)\n    const helpers = this.createParseHelpers()\n\n    // Try each handler until one returns a valid result\n    const result = handlers.find(handler => {\n      if (!handler.parseMarkdown) {\n        return false\n      }\n\n      const parseResult = handler.parseMarkdown(token, helpers)\n      const normalized = this.normalizeParseResult(parseResult)\n\n      // Check if this handler returned a valid result (not null/empty array)\n      if (normalized && (!Array.isArray(normalized) || normalized.length > 0)) {\n        // Store result for return\n        this.lastParseResult = normalized\n        return true\n      }\n\n      return false\n    })\n\n    // If a handler worked, return its result\n    if (result && this.lastParseResult) {\n      const toReturn = this.lastParseResult\n      this.lastParseResult = null // Clean up\n      return toReturn\n    }\n\n    // If no handler worked, try fallback parsing\n    return this.parseFallbackToken(token)\n  }\n\n  /**\n   * Creates helper functions for parsing markdown tokens.\n   * @returns An object containing helper functions for parsing.\n   */\n  private createParseHelpers(): MarkdownParseHelpers {\n    return {\n      parseInline: (tokens: MarkdownToken[]) => this.parseInlineTokens(tokens),\n      parseChildren: (tokens: MarkdownToken[]) => this.parseTokens(tokens),\n      parseBlockChildren: (tokens: MarkdownToken[]) => this.parseTokens(tokens, true),\n      createTextNode: (text: string, marks?: Array<{ type: string; attrs?: any }>) => {\n        const node = {\n          type: 'text',\n          text,\n          marks: marks || undefined,\n        }\n\n        return node\n      },\n      createNode: (type: string, attrs?: any, content?: JSONContent[]) => {\n        const node = {\n          type,\n          attrs: attrs || undefined,\n          content: content || undefined,\n        }\n\n        if (!attrs || Object.keys(attrs).length === 0) {\n          delete node.attrs\n        }\n\n        return node\n      },\n      applyMark: (markType: string, content: JSONContent[], attrs?: any) => ({\n        mark: markType,\n        content,\n        attrs: attrs && Object.keys(attrs).length > 0 ? attrs : undefined,\n      }),\n    }\n  }\n\n  /**\n   * Escape special regex characters in a string.\n   */\n  private escapeRegex(str: string): string {\n    return str.replace(/[.*+?^${}()|[\\]\\\\]/g, '\\\\$&')\n  }\n\n  /**\n   * Parse inline tokens (bold, italic, links, etc.) into text nodes with marks.\n   * This is the complex part that handles mark nesting and boundaries.\n   */\n  private parseInlineTokens(tokens: MarkdownToken[]): JSONContent[] {\n    const result: JSONContent[] = []\n\n    // Process tokens sequentially using an index so we can lookahead and\n    // merge split inline HTML fragments like: text / <em> / inner / </em> / text\n    for (let i = 0; i < tokens.length; i += 1) {\n      const token = tokens[i]\n\n      if (token.type === 'text') {\n        result.push({\n          type: 'text',\n          text: token.text || '',\n        })\n      } else if (token.type === 'html') {\n        // Handle possible split inline HTML by attempting to detect an\n        // opening tag and searching forward for a matching closing tag.\n        const raw = (token.raw ?? token.text ?? '').toString()\n\n        // Quick checks for opening vs. closing tag\n        const isClosing = /^<\\/[\\s]*[\\w-]+/i.test(raw)\n        const openMatch = raw.match(/^<[\\s]*([\\w-]+)(\\s|>|\\/|$)/i)\n\n        if (!isClosing && openMatch && !/\\/>$/.test(raw)) {\n          // Try to find the corresponding closing html token for this tag\n          const tagName = openMatch[1]\n          const escapedTagName = this.escapeRegex(tagName)\n          const closingRegex = new RegExp(`^<\\\\/\\\\s*${escapedTagName}\\\\b`, 'i')\n          let foundIndex = -1\n\n          // Collect intermediate raw parts to reconstruct full HTML fragment\n          const parts: string[] = [raw]\n          for (let j = i + 1; j < tokens.length; j += 1) {\n            const t = tokens[j]\n            const tRaw = (t.raw ?? t.text ?? '').toString()\n            parts.push(tRaw)\n            if (t.type === 'html' && closingRegex.test(tRaw)) {\n              foundIndex = j\n              break\n            }\n          }\n\n          if (foundIndex !== -1) {\n            // Merge opening + inner + closing into one html fragment and parse\n            const mergedRaw = parts.join('')\n            const mergedToken = {\n              type: 'html',\n              raw: mergedRaw,\n              text: mergedRaw,\n              block: false,\n            } as unknown as MarkdownToken\n\n            const parsed = this.parseHTMLToken(mergedToken)\n            if (parsed) {\n              const normalized = this.normalizeParseResult(parsed as any)\n              if (Array.isArray(normalized)) {\n                result.push(...normalized)\n              } else if (normalized) {\n                result.push(normalized)\n              }\n            }\n\n            // Advance i to the closing token\n            i = foundIndex\n            continue\n          }\n        }\n\n        // Fallback: single html token parse\n        const parsedSingle = this.parseHTMLToken(token)\n        if (parsedSingle) {\n          const normalized = this.normalizeParseResult(parsedSingle as any)\n          if (Array.isArray(normalized)) {\n            result.push(...normalized)\n          } else if (normalized) {\n            result.push(normalized)\n          }\n        }\n      } else if (token.type) {\n        // Handle inline marks (bold, italic, etc.)\n        const markHandler = this.getHandlerForToken(token.type)\n        if (markHandler && markHandler.parseMarkdown) {\n          const helpers = this.createParseHelpers()\n          const parsed = markHandler.parseMarkdown(token, helpers)\n\n          if (this.isMarkResult(parsed)) {\n            // This is a mark result - apply the mark to the content\n            const markedContent = this.applyMarkToContent(parsed.mark, parsed.content, parsed.attrs)\n            result.push(...markedContent)\n          } else {\n            // Regular inline node\n            const normalized = this.normalizeParseResult(parsed)\n            if (Array.isArray(normalized)) {\n              result.push(...normalized)\n            } else if (normalized) {\n              result.push(normalized)\n            }\n          }\n        } else if (token.tokens) {\n          // Fallback: try to parse children if they exist\n          result.push(...this.parseInlineTokens(token.tokens))\n        }\n      }\n    }\n\n    return result\n  }\n\n  /**\n   * Apply a mark to content nodes.\n   */\n  private applyMarkToContent(markType: string, content: JSONContent[], attrs?: any): JSONContent[] {\n    return content.map(node => {\n      if (node.type === 'text') {\n        // Add the mark to existing marks or create new marks array\n        const existingMarks = node.marks || []\n        const newMark = attrs ? { type: markType, attrs } : { type: markType }\n        return {\n          ...node,\n          marks: [...existingMarks, newMark],\n        }\n      }\n\n      // For non-text nodes, recursively apply to content\n      return {\n        ...node,\n        content: node.content ? this.applyMarkToContent(markType, node.content, attrs) : undefined,\n      }\n    })\n  } /**\n   * Check if a parse result represents a mark to be applied.\n   */\n  private isMarkResult(result: any): result is { mark: string; content: JSONContent[]; attrs?: any } {\n    return result && typeof result === 'object' && 'mark' in result\n  }\n\n  /**\n   * Normalize parse results to ensure they're valid JSONContent.\n   */\n  private normalizeParseResult(result: MarkdownParseResult): JSONContent | JSONContent[] | null {\n    if (!result) {\n      return null\n    }\n\n    if (this.isMarkResult(result)) {\n      // This shouldn't happen at the top level, but handle it gracefully\n      return result.content\n    }\n\n    return result as JSONContent | JSONContent[]\n  }\n\n  /**\n   * Fallback parsing for common tokens when no specific handler is registered.\n   */\n  private parseFallbackToken(\n    token: MarkdownToken,\n    parseImplicitEmptyParagraphs = false,\n  ): JSONContent | JSONContent[] | null {\n    switch (token.type) {\n      case 'paragraph':\n        return {\n          type: 'paragraph',\n          content: token.tokens ? this.parseInlineTokens(token.tokens) : [],\n        }\n\n      case 'heading':\n        return {\n          type: 'heading',\n          attrs: { level: token.depth || 1 },\n          content: token.tokens ? this.parseInlineTokens(token.tokens) : [],\n        }\n\n      case 'text':\n        return {\n          type: 'text',\n          text: token.text || '',\n        }\n\n      case 'html':\n        // Parse HTML using extensions' parseHTML methods\n        return this.parseHTMLToken(token)\n\n      case 'space':\n        return null\n\n      default:\n        // Unknown token type - try to parse children if they exist\n        if (token.tokens) {\n          return this.parseTokens(token.tokens, parseImplicitEmptyParagraphs)\n        }\n        return null\n    }\n  }\n\n  /**\n   * Parse HTML tokens using extensions' parseHTML methods.\n   * This allows HTML within markdown to be parsed according to extension rules.\n   */\n  private parseHTMLToken(token: MarkdownToken): JSONContent | JSONContent[] | null {\n    const html = token.text || token.raw || ''\n\n    if (!html.trim()) {\n      return null\n    }\n\n    // Check if we're in a server-side environment (no window object)\n    // If so, fall back to treating HTML as plain text to avoid runtime errors\n    if (typeof window === 'undefined') {\n      // For block-level HTML, wrap in a paragraph to maintain valid document structure\n      if (token.block) {\n        return {\n          type: 'paragraph',\n          content: [\n            {\n              type: 'text',\n              text: html,\n            },\n          ],\n        }\n      }\n      // For inline HTML, return plain text\n      return {\n        type: 'text',\n        text: html,\n      }\n    }\n\n    // Use generateJSON to parse the HTML using extensions' parseHTML rules\n    try {\n      const parsed = generateJSON(html, this.baseExtensions)\n\n      // If the result is a doc node, extract its content\n      if (parsed.type === 'doc' && parsed.content) {\n        // For block-level HTML, return the content array\n        if (token.block) {\n          return parsed.content\n        }\n\n        // For inline HTML, we need to flatten the content appropriately\n        // If there's only one paragraph with content, unwrap it\n        if (parsed.content.length === 1 && parsed.content[0].type === 'paragraph' && parsed.content[0].content) {\n          return parsed.content[0].content\n        }\n\n        return parsed.content\n      }\n\n      return parsed as JSONContent\n    } catch (error) {\n      throw new Error(`Failed to parse HTML in markdown: ${error}`)\n    }\n  }\n\n  renderNodeToMarkdown(\n    node: JSONContent,\n    parentNode?: JSONContent,\n    index = 0,\n    level = 0,\n    meta: Record<string, any> = {},\n  ): string {\n    // if node is a text node, we simply return it's text content\n    // marks are handled at the array level in renderNodesWithMarkBoundaries\n    if (node.type === 'text') {\n      return node.text || ''\n    }\n\n    if (!node.type) {\n      return ''\n    }\n\n    const handler = this.getHandlerForToken(node.type)\n    if (!handler) {\n      return ''\n    }\n\n    const previousNode = Array.isArray(parentNode?.content) && index > 0 ? parentNode.content[index - 1] : undefined\n    const helpers: MarkdownRendererHelpers = {\n      renderChildren: (nodes, separator) => {\n        const childLevel = handler.isIndenting ? level + 1 : level\n\n        if (!Array.isArray(nodes) && (nodes as any).content) {\n          return this.renderNodes((nodes as any).content as JSONContent[], node, separator || '', index, childLevel)\n        }\n\n        return this.renderNodes(nodes, node, separator || '', index, childLevel)\n      },\n      renderChild: (childNode, childIndex) => {\n        const childLevel = handler.isIndenting ? level + 1 : level\n\n        return this.renderNodeToMarkdown(childNode, node, childIndex, childLevel)\n      },\n      indent: content => {\n        return this.indentString + content\n      },\n      wrapInBlock: wrapInMarkdownBlock,\n    }\n\n    const context: RenderContext = {\n      index,\n      level,\n      parentType: parentNode?.type,\n      previousNode,\n      meta: {\n        parentAttrs: parentNode?.attrs,\n        ...meta,\n      },\n    }\n\n    // First render the node itself (this will render children recursively)\n    const rendered = handler.renderMarkdown?.(node, helpers, context) || ''\n\n    return rendered\n  }\n\n  /**\n   * Render a node or an array of nodes. Parent type controls how children\n   * are joined (which determines newline insertion between children).\n   */\n  renderNodes(\n    nodeOrNodes: JSONContent | JSONContent[],\n    parentNode?: JSONContent,\n    separator = '',\n    index = 0,\n    level = 0,\n  ): string {\n    // if we have just one node, call renderNodeToMarkdown directly\n    if (!Array.isArray(nodeOrNodes)) {\n      if (!nodeOrNodes.type) {\n        return ''\n      }\n\n      return this.renderNodeToMarkdown(nodeOrNodes, parentNode, index, level)\n    }\n\n    return this.renderNodesWithMarkBoundaries(nodeOrNodes, parentNode, separator, level)\n  }\n\n  /**\n   * Render an array of nodes while properly tracking mark boundaries.\n   * This handles cases where marks span across multiple text nodes.\n   */\n  private renderNodesWithMarkBoundaries(\n    nodes: JSONContent[],\n    parentNode?: JSONContent,\n    separator = '',\n    level = 0,\n  ): string {\n    const result: string[] = []\n    const activeMarks: Map<string, any> = new Map()\n    const reopenWithHtmlOnNextOpen = new Set<string>()\n    const markOpeningModes = new Map<string, 'markdown' | 'html'>()\n    nodes.forEach((node, i) => {\n      // Lookahead to the next node to determine if marks need to be closed\n      const nextNode = i < nodes.length - 1 ? nodes[i + 1] : null\n\n      if (!node.type) {\n        return\n      }\n\n      if (node.type === 'text') {\n        let textContent = node.text || ''\n        const currentMarks = new Map((node.marks || []).map(mark => [mark.type, mark]))\n\n        // Find marks that need to be closed and opened\n        const marksToOpen = findMarksToOpen(activeMarks, currentMarks)\n        const marksToClose = findMarksToClose(currentMarks, nextNode)\n\n        // When marks simultaneously close (old) AND open (new) at this boundary, the naive\n        // approach of appending old-close and prepending new-open produces interleaved\n        // delimiters like `*456**` (italic open, text, bold close) instead of properly\n        // nested `_456_**` (italic open, text, italic close, bold close).\n        //\n        // The fix: when both are present, defer old mark closings to the end of the node\n        // (after the new marks also close), ensuring correct inner-before-outer order.\n        //\n        // If an already-active mark ends on this node while another mark opens on this same\n        // node, we defer closing the active mark until the end of the node so nesting stays\n        // valid (`**...++abc++**` instead of `**...++abc**++`).\n        const activeMarksClosingHere = marksToClose.filter(markType => activeMarks.has(markType))\n        const hasCrossedBoundary = activeMarksClosingHere.length > 0 && marksToOpen.length > 0\n\n        let middleTrailingWhitespace = ''\n\n        if (marksToClose.length > 0 && !hasCrossedBoundary) {\n          // Extract trailing whitespace before closing marks to prevent invalid markdown like \"**text **\"\n          const middleTrailingMatch = textContent.match(/(\\s+)$/)\n          if (middleTrailingMatch) {\n            middleTrailingWhitespace = middleTrailingMatch[1]\n            textContent = textContent.slice(0, -middleTrailingWhitespace.length)\n          }\n        }\n\n        if (!hasCrossedBoundary) {\n          // Normal path: close marks that are ending here (no new marks opening simultaneously)\n          marksToClose.forEach(markType => {\n            if (!activeMarks.has(markType)) {\n              return\n            }\n\n            const mark = currentMarks.get(markType)\n            const closeMarkdown = this.getMarkClosing(markType, mark, markOpeningModes.get(markType))\n            if (closeMarkdown) {\n              textContent += closeMarkdown\n            }\n            if (activeMarks.has(markType)) {\n              activeMarks.delete(markType)\n              markOpeningModes.delete(markType)\n            }\n          })\n        }\n\n        // Open new marks (should be at the beginning)\n        // Extract leading whitespace before opening marks to prevent invalid markdown like \"** text**\"\n        let leadingWhitespace = ''\n        if (marksToOpen.length > 0) {\n          const leadingMatch = textContent.match(/^(\\s+)/)\n          if (leadingMatch) {\n            leadingWhitespace = leadingMatch[1]\n            textContent = textContent.slice(leadingWhitespace.length)\n          }\n        }\n\n        // Snapshot active mark types before opening new marks, so each new mark's delimiter\n        // is chosen based on what is already active (not including itself).\n        // When crossing a boundary, old marks are still in activeMarks here (not yet removed),\n        // so new marks correctly see them as active context.\n        marksToOpen.forEach(({ type, mark }) => {\n          const openingMode = reopenWithHtmlOnNextOpen.has(type) ? 'html' : 'markdown'\n          const openMarkdown = this.getMarkOpening(type, mark, openingMode)\n          if (openMarkdown) {\n            textContent = openMarkdown + textContent\n          }\n          markOpeningModes.set(type, openingMode)\n          reopenWithHtmlOnNextOpen.delete(type)\n        })\n\n        if (!hasCrossedBoundary) {\n          marksToOpen\n            .slice()\n            .reverse()\n            .forEach(({ type, mark }) => {\n              activeMarks.set(type, mark)\n            })\n        }\n\n        // Add leading whitespace before the mark opening\n        textContent = leadingWhitespace + textContent\n\n        // Determine marks to close at the end of this node.\n        // On a crossed boundary, we close new marks (inner) first, then old marks (outer),\n        // ensuring correct nesting order. Both sets are removed from activeMarks so the\n        // next node's marksToOpen will reopen whichever ones continue.\n        let marksToCloseAtEnd: string[]\n        if (hasCrossedBoundary) {\n          const nextMarkTypes = new Set((nextNode?.marks || []).map((mark: any) => mark.type))\n\n          marksToOpen.forEach(({ type }) => {\n            if (nextMarkTypes.has(type) && this.getHtmlReopenTags(type)) {\n              reopenWithHtmlOnNextOpen.add(type)\n            }\n          })\n\n          marksToCloseAtEnd = [\n            ...marksToOpen.map(m => m.type), // inner (opened here) — close first\n            ...activeMarksClosingHere, // outer (were active before) — close last\n          ]\n        } else {\n          marksToCloseAtEnd = findMarksToCloseAtEnd(activeMarks, currentMarks, nextNode, this.markSetsEqual.bind(this))\n        }\n\n        // Extract trailing whitespace before closing marks to prevent invalid markdown like \"**text **\"\n        let trailingWhitespace = ''\n        if (marksToCloseAtEnd.length > 0) {\n          const trailingMatch = textContent.match(/(\\s+)$/)\n          if (trailingMatch) {\n            trailingWhitespace = trailingMatch[1]\n            textContent = textContent.slice(0, -trailingWhitespace.length)\n          }\n        }\n\n        marksToCloseAtEnd.forEach(markType => {\n          const mark = activeMarks.get(markType) ?? currentMarks.get(markType)\n          const closeMarkdown = this.getMarkClosing(markType, mark, markOpeningModes.get(markType))\n          if (closeMarkdown) {\n            textContent += closeMarkdown\n          }\n          activeMarks.delete(markType)\n          markOpeningModes.delete(markType)\n        })\n\n        // Add trailing whitespace after the mark closing\n        textContent += trailingWhitespace\n        textContent += middleTrailingWhitespace\n\n        result.push(textContent)\n      } else {\n        // For non-text nodes, close all active marks before rendering, then reopen after\n        const marksToReopen = new Map(activeMarks)\n        const openingModesToReopen = new Map(markOpeningModes)\n\n        // Close all marks before the node\n        const beforeMarkdown = closeMarksBeforeNode(activeMarks, (markType, mark) => {\n          return this.getMarkClosing(markType, mark, markOpeningModes.get(markType))\n        })\n        markOpeningModes.clear()\n\n        // Render the node\n        const nodeContent = this.renderNodeToMarkdown(node, parentNode, i, level)\n\n        // Reopen marks after the node, but NOT after a hard break\n        // Hard breaks should terminate marks (they create a line break where marks don't continue)\n        const afterMarkdown =\n          node.type === 'hardBreak'\n            ? ''\n            : reopenMarksAfterNode(marksToReopen, activeMarks, (markType, mark) => {\n                const openingMode = openingModesToReopen.get(markType) ?? 'markdown'\n                markOpeningModes.set(markType, openingMode)\n                return this.getMarkOpening(markType, mark, openingMode)\n              })\n\n        result.push(beforeMarkdown + nodeContent + afterMarkdown)\n      }\n    })\n\n    return result.join(separator)\n  }\n\n  /**\n   * Get the opening markdown syntax for a mark type.\n   */\n  private getMarkOpening(markType: string, mark: any, openingMode: 'markdown' | 'html' = 'markdown'): string {\n    if (openingMode === 'html') {\n      return this.getHtmlReopenTags(markType)?.open || ''\n    }\n\n    const handlers = this.getHandlersForNodeType(markType)\n    const handler = handlers.length > 0 ? handlers[0] : undefined\n    if (!handler || !handler.renderMarkdown) {\n      return ''\n    }\n\n    // Use a unique placeholder that's extremely unlikely to appear in real content\n    const placeholder = '\\uE000__TIPTAP_MARKDOWN_PLACEHOLDER__\\uE001'\n\n    // For most marks, we can extract the opening syntax by rendering a simple case\n    const syntheticNode: JSONContent = {\n      type: markType,\n      attrs: mark.attrs || {},\n      content: [{ type: 'text', text: placeholder }],\n    }\n\n    try {\n      const rendered = handler.renderMarkdown(\n        syntheticNode,\n        {\n          renderChildren: () => placeholder,\n          renderChild: () => placeholder,\n          indent: (content: string) => content,\n          wrapInBlock: (prefix: string, content: string) => prefix + content,\n        },\n        { index: 0, level: 0, parentType: 'text', meta: {} },\n      )\n\n      // Extract the opening part (everything before placeholder)\n      const placeholderIndex = rendered.indexOf(placeholder)\n      return placeholderIndex >= 0 ? rendered.substring(0, placeholderIndex) : ''\n    } catch (err) {\n      throw new Error(`Failed to get mark opening for ${markType}: ${err}`)\n    }\n  }\n\n  /**\n   * Get the closing markdown syntax for a mark type.\n   */\n  private getMarkClosing(markType: string, mark: any, openingMode: 'markdown' | 'html' = 'markdown'): string {\n    if (openingMode === 'html') {\n      return this.getHtmlReopenTags(markType)?.close || ''\n    }\n\n    const handlers = this.getHandlersForNodeType(markType)\n    const handler = handlers.length > 0 ? handlers[0] : undefined\n    if (!handler || !handler.renderMarkdown) {\n      return ''\n    }\n\n    // Use a unique placeholder that's extremely unlikely to appear in real content\n    const placeholder = '\\uE000__TIPTAP_MARKDOWN_PLACEHOLDER__\\uE001'\n\n    const syntheticNode: JSONContent = {\n      type: markType,\n      attrs: mark.attrs || {},\n      content: [{ type: 'text', text: placeholder }],\n    }\n\n    try {\n      const rendered = handler.renderMarkdown(\n        syntheticNode,\n        {\n          renderChildren: () => placeholder,\n          renderChild: () => placeholder,\n          indent: (content: string) => content,\n          wrapInBlock: (prefix: string, content: string) => prefix + content,\n        },\n        { index: 0, level: 0, parentType: 'text', meta: {} },\n      )\n\n      // Extract the closing part (everything after placeholder)\n      const placeholderIndex = rendered.indexOf(placeholder)\n      const placeholderEnd = placeholderIndex + placeholder.length\n      return placeholderIndex >= 0 ? rendered.substring(placeholderEnd) : ''\n    } catch (err) {\n      throw new Error(`Failed to get mark closing for ${markType}: ${err}`)\n    }\n  }\n\n  /**\n   * Returns the inline HTML tags an extension exposes for overlap-boundary\n   * reopen handling, if that mark explicitly opted into HTML reopen mode.\n   */\n  private getHtmlReopenTags(markType: string): { open: string; close: string } | undefined {\n    const handlers = this.getHandlersForNodeType(markType)\n    const handler = handlers.length > 0 ? handlers[0] : undefined\n\n    return handler?.htmlReopen\n  }\n\n  /**\n   * Check if two mark sets are equal.\n   */\n  private markSetsEqual(marks1: Map<string, any>, marks2: Map<string, any>): boolean {\n    if (marks1.size !== marks2.size) {\n      return false\n    }\n\n    return Array.from(marks1.keys()).every(type => marks2.has(type))\n  }\n}\n\nexport default MarkdownManager\n","import type { Content, MarkdownToken } from '@tiptap/core'\nimport type { Fragment, Node } from '@tiptap/pm/model'\n\nimport type { ContentType } from './types.js'\n\n/**\n * Wraps each line of the content with the given prefix.\n * @param prefix The prefix to wrap each line with.\n * @param content The content to wrap.\n * @returns The content with each line wrapped with the prefix.\n */\nexport function wrapInMarkdownBlock(prefix: string, content: string) {\n  // split content lines\n  const lines = content.split('\\n')\n\n  // add empty strings between every line\n  const output = lines\n    // add empty lines between each block\n    .flatMap(line => [line, ''])\n    // add the prefix to each line\n    .map(line => `${prefix}${line}`)\n    .join('\\n')\n\n  return output.slice(0, output.length - 1)\n}\n\n/**\n * Identifies marks that need to be closed, based on the marks in the next node.\n */\nexport function findMarksToClose(currentMarks: Map<string, any>, nextNode: any): string[] {\n  const marksToClose: string[] = []\n\n  Array.from(currentMarks.keys()).forEach(markType => {\n    if (!nextNode || !nextNode.marks || !nextNode.marks.map((mark: any) => mark.type).includes(markType)) {\n      marksToClose.push(markType)\n    }\n  })\n  return marksToClose\n}\n\n/**\n * Identifies marks that need to be opened (in current node but not active).\n */\nexport function findMarksToOpen(\n  activeMarks: Map<string, any>,\n  currentMarks: Map<string, any>,\n): Array<{ type: string; mark: any }> {\n  const marksToOpen: Array<{ type: string; mark: any }> = []\n  Array.from(currentMarks.entries()).forEach(([markType, mark]) => {\n    if (!activeMarks.has(markType)) {\n      marksToOpen.push({ type: markType, mark })\n    }\n  })\n  return marksToOpen\n}\n\n/**\n * Determines which marks need to be closed at the end of the current text node.\n * This handles cases where marks end at node boundaries or when transitioning\n * to nodes with different mark sets.\n */\nexport function findMarksToCloseAtEnd(\n  activeMarks: Map<string, any>,\n  currentMarks: Map<string, any>,\n  nextNode: any,\n  markSetsEqual: (a: Map<string, any>, b: Map<string, any>) => boolean,\n): string[] {\n  const isLastNode = !nextNode\n  const nextNodeHasNoMarks = nextNode && nextNode.type === 'text' && (!nextNode.marks || nextNode.marks.length === 0)\n  const nextNodeHasDifferentMarks =\n    nextNode &&\n    nextNode.type === 'text' &&\n    nextNode.marks &&\n    !markSetsEqual(currentMarks, new Map(nextNode.marks.map((mark: any) => [mark.type, mark])))\n\n  const marksToCloseAtEnd: string[] = []\n  if (isLastNode || nextNodeHasNoMarks || nextNodeHasDifferentMarks) {\n    if (nextNode && nextNode.type === 'text' && nextNode.marks) {\n      const nextMarks = new Map(nextNode.marks.map((mark: any) => [mark.type, mark]))\n      Array.from(activeMarks.keys())\n        .reverse()\n        .forEach(markType => {\n          if (!nextMarks.has(markType)) {\n            marksToCloseAtEnd.push(markType)\n          }\n        })\n    } else if (isLastNode || nextNodeHasNoMarks) {\n      // Close all active marks\n      marksToCloseAtEnd.push(...Array.from(activeMarks.keys()).reverse())\n    }\n  }\n\n  return marksToCloseAtEnd\n}\n\n/**\n * Closes active marks before rendering a non-text node.\n * Returns the closing markdown syntax and clears the active marks.\n */\nexport function closeMarksBeforeNode(\n  activeMarks: Map<string, any>,\n  getMarkClosing: (markType: string, mark: any) => string,\n): string {\n  let beforeMarkdown = ''\n  Array.from(activeMarks.keys())\n    .reverse()\n    .forEach(markType => {\n      const mark = activeMarks.get(markType)\n      const closeMarkdown = getMarkClosing(markType, mark)\n      if (closeMarkdown) {\n        beforeMarkdown = closeMarkdown + beforeMarkdown\n      }\n    })\n  activeMarks.clear()\n  return beforeMarkdown\n}\n\n/**\n * Reopens marks after rendering a non-text node.\n * Returns the opening markdown syntax and updates the active marks.\n */\nexport function reopenMarksAfterNode(\n  marksToReopen: Map<string, any>,\n  activeMarks: Map<string, any>,\n  getMarkOpening: (markType: string, mark: any) => string,\n): string {\n  let afterMarkdown = ''\n  Array.from(marksToReopen.entries()).forEach(([markType, mark]) => {\n    const openMarkdown = getMarkOpening(markType, mark)\n    if (openMarkdown) {\n      afterMarkdown += openMarkdown\n    }\n    activeMarks.set(markType, mark)\n  })\n  return afterMarkdown\n}\n\n/**\n * Check if a markdown list item token is a task item and extract its state.\n *\n * @param item The list item token to check\n * @returns Object containing isTask flag, checked state, and indentation level\n *\n * @example\n * ```ts\n * isTaskItem({ raw: '- [ ] Task' }) // { isTask: true, checked: false, indentLevel: 0 }\n * isTaskItem({ raw: '  - [x] Done' }) // { isTask: true, checked: true, indentLevel: 2 }\n * isTaskItem({ raw: '- Regular' }) // { isTask: false, indentLevel: 0 }\n * ```\n */\nexport function isTaskItem(item: MarkdownToken): { isTask: boolean; checked?: boolean; indentLevel: number } {\n  const raw = item.raw || item.text || ''\n\n  // Match patterns like \"- [ ] \" or \"  - [x] \"\n  const match = raw.match(/^(\\s*)[-+*]\\s+\\[([ xX])\\]\\s+/)\n\n  if (match) {\n    return { isTask: true, checked: match[2].toLowerCase() === 'x', indentLevel: match[1].length }\n  }\n  return { isTask: false, indentLevel: 0 }\n}\n\n/**\n * Assumes the content type based off the content.\n * @param content The content to assume the type for.\n * @param contentType The content type that should be prioritized.\n */\nexport function assumeContentType(\n  content: (Content | Fragment | Node) | string,\n  contentType: ContentType,\n): ContentType {\n  // if not a string, we assume it will be a json content object\n  if (typeof content !== 'string') {\n    return 'json'\n  }\n\n  // otherwise we let the content type be what it is\n  return 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package/package.json

@@ -1,7 +1,7 @@
 {
   "name": "@tiptap/markdown",
   "description": "markdown parser and serializer for tiptap",
-  "version": "3.20.6",
+  "version": "3.21.0",
   "homepage": "https://tiptap.dev",
   "keywords": [
     "tiptap",
@@ -37,12 +37,12 @@
     "marked": "^17.0.1"
   },
   "devDependencies": {
-    "@tiptap/core": "^3.20.6",
-    "@tiptap/pm": "^3.20.6"
+    "@tiptap/core": "^3.21.0",
+    "@tiptap/pm": "^3.21.0"
   },
   "peerDependencies": {
-    "@tiptap/core": "^3.20.6",
-    "@tiptap/pm": "^3.20.6"
+    "@tiptap/core": "^3.21.0",
+    "@tiptap/pm": "^3.21.0"
   },
   "repository": {
     "type": "git",

package/src/MarkdownManager.ts

@@ -3,6 +3,7 @@ import {
   type ExtendableConfig,
   type JSONContent,
   type MarkdownExtensionSpec,
+  type MarkdownLexerConfiguration,
   type MarkdownParseHelpers,
   type MarkdownParseResult,
   type MarkdownRendererHelpers,
@@ -13,7 +14,7 @@ import {
   generateJSON,
   getExtensionField,
 } from '@tiptap/core'
-import { type Lexer, type Token, type TokenizerExtension, marked } from 'marked'
+import { type Lexer, type Token, type TokenizerExtension, type TokenizerThis, marked } from 'marked'
 
 import {
   closeMarksBeforeNode,
@@ -27,7 +28,7 @@ import {
 
 export class MarkdownManager {
   private markedInstance: typeof marked
-  private lexer: Lexer
+  private activeParseLexer: Lexer | null = null
   private registry: Map<string, MarkdownExtensionSpec[]>
   private nodeTypeRegistry: Map<string, MarkdownExtensionSpec[]>
   private indentStyle: 'space' | 'tab'
@@ -49,7 +50,6 @@ export class MarkdownManager {
     extensions: AnyExtension[]
   }) {
     this.markedInstance = options?.marked ?? marked
-    this.lexer = new this.markedInstance.Lexer()
     this.indentStyle = options?.indentation?.style ?? 'space'
     this.indentSize = options?.indentation?.size ?? 2
     this.baseExtensions = options?.extensions || []
@@ -65,9 +65,8 @@ export class MarkdownManager {
     if (options?.extensions) {
       this.baseExtensions = options.extensions
       const flattened = flattenExtensions(options.extensions)
-      flattened.forEach(ext => this.registerExtension(ext, false))
+      flattened.forEach(ext => this.registerExtension(ext))
     }
-    this.lexer = new this.markedInstance.Lexer() // Reset lexer to include all tokenizers
   }
 
   /** Returns the underlying marked instance. */
@@ -95,7 +94,7 @@ export class MarkdownManager {
    * `markdownName`, `parseMarkdown`, `renderMarkdown` and `priority` from the
    * extension config (using the same resolution used across the codebase).
    */
-  registerExtension(extension: AnyExtension, recreateLexer: boolean = true): void {
+  registerExtension(extension: AnyExtension): void {
     // Keep track of all extensions for HTML parsing
     this.extensions.push(extension)
 
@@ -143,13 +142,24 @@ export class MarkdownManager {
     // Register custom tokenizer with marked.js
     if (tokenizer && this.hasMarked()) {
       this.registerTokenizer(tokenizer)
+    }
+  }
 
-      if (recreateLexer) {
-        this.lexer = new this.markedInstance.Lexer() // Reset lexer to include new tokenizer
-      }
+  private createLexer(): Lexer {
+    return new this.markedInstance.Lexer()
+  }
+
+  private createTokenizerHelpers(lexer: Lexer): MarkdownLexerConfiguration {
+    return {
+      inlineTokens: (src: string) => lexer.inlineTokens(src),
+      blockTokens: (src: string) => lexer.blockTokens(src),
     }
   }
 
+  private tokenizeInline(src: string): MarkdownToken[] {
+    return (this.activeParseLexer ?? this.createLexer()).inlineTokens(src) as MarkdownToken[]
+  }
+
   /**
    * Register a custom tokenizer with marked.js for parsing non-standard markdown syntax.
    */
@@ -159,27 +169,15 @@ export class MarkdownManager {
     }
 
     const { name, start, level = 'inline', tokenize } = tokenizer
-
-    // Helper functions that use a fresh lexer instance with all registered extensions
-    const tokenizeInline = (src: string) => {
-      return this.lexer.inlineTokens(src)
-    }
-
-    const tokenizeBlock = (src: string) => {
-      return this.lexer.blockTokens(src)
-    }
-
-    const helper = {
-      inlineTokens: tokenizeInline,
-      blockTokens: tokenizeBlock,
-    }
+    const createTokenizerHelpers = this.createTokenizerHelpers.bind(this)
+    const createLexer = this.createLexer.bind(this)
 
     let startCb: (src: string) => number
 
     if (!start) {
       startCb = (src: string) => {
         // For other tokenizers, try to find a match and return its position
-        const result = tokenize(src, [], helper)
+        const result = tokenize(src, [], this.createTokenizerHelpers(this.createLexer()))
         if (result && result.raw) {
           const index = src.indexOf(result.raw)
           return index
@@ -195,7 +193,8 @@ export class MarkdownManager {
       name,
       level,
       start: startCb,
-      tokenizer: (src, tokens) => {
+      tokenizer(this: TokenizerThis, src, tokens) {
+        const helper = this.lexer ? createTokenizerHelpers(this.lexer) : createTokenizerHelpers(createLexer())
         const result = tokenize(src, tokens, helper)
 
         if (result && result.type) {
@@ -289,16 +288,26 @@ export class MarkdownManager {
       throw new Error('No marked instance available for parsing')
     }
 
-    // Use marked to tokenize the markdown
-    const tokens = this.markedInstance.lexer(markdown)
+    const previousParseLexer = this.activeParseLexer
+    const parseLexer = this.createLexer()
 
-    // Convert tokens to Tiptap JSON
-    const content = this.parseTokens(tokens, true)
+    this.activeParseLexer = parseLexer
 
-    // Return a document node containing the parsed content
-    return {
-      type: 'doc',
-      content,
+    try {
+      // Use a parse-scoped lexer so follow-up inline tokenization can reuse
+      // the same configured lexer state without sharing it across parses.
+      const tokens = parseLexer.lex(markdown) as MarkdownToken[]
+
+      // Convert tokens to Tiptap JSON
+      const content = this.parseTokens(tokens, true)
+
+      // Return a document node containing the parsed content
+      return {
+        type: 'doc',
+        content,
+      }
+    } finally {
+      this.activeParseLexer = previousParseLexer
     }
   }
 
@@ -491,7 +500,7 @@ export class MarkdownManager {
           indentLevel,
           checked: checked ?? false,
           text: mainContent,
-          tokens: this.lexer.inlineTokens(mainContent),
+          tokens: this.tokenizeInline(mainContent),
           nestedTokens,
         }
       }