@librechat/agents 3.2.67 → 3.2.68

package/dist/cjs/llm/google/index.cjs

@@ -120,6 +120,7 @@ var CustomChatGoogleGenerativeAI = class extends _langchain_google_genai.ChatGoo
 			this.client.systemInstruction = systemInstruction;
 			actualPrompt = prompt.slice(1);
 		}
+		actualPrompt = require_common.dropUnsupportedModelTurnPrefill(actualPrompt, this.model);
 		const request = {
 			...this.invocationParams(options),
 			contents: actualPrompt
@@ -143,6 +144,7 @@ var CustomChatGoogleGenerativeAI = class extends _langchain_google_genai.ChatGoo
 			this.client.systemInstruction = systemInstruction;
 			actualPrompt = prompt.slice(1);
 		}
+		actualPrompt = require_common.dropUnsupportedModelTurnPrefill(actualPrompt, this.model);
 		const request = {
 			...this.invocationParams(options),
 			contents: actualPrompt

package/dist/cjs/llm/google/index.cjs.map

@@ -1 +1 @@
-{"version":3,"file":"index.cjs","names":["ChatGoogleGenerativeAI","GenerativeAI","FunctionCallingMode","convertBaseMessagesToContent","mapGenerateContentResultToChatResult","convertResponseContentToChatGenerationChunk","ChatGenerationChunk","AIMessageChunk"],"sources":["../../../../src/llm/google/index.ts"],"sourcesContent":["/* eslint-disable @typescript-eslint/ban-ts-comment */\nimport { AIMessageChunk } from '@langchain/core/messages';\nimport { ChatGenerationChunk } from '@langchain/core/outputs';\nimport { ChatGoogleGenerativeAI } from '@langchain/google-genai';\nimport { getEnvironmentVariable } from '@langchain/core/utils/env';\nimport {\n  FunctionCallingMode,\n  GoogleGenerativeAI as GenerativeAI,\n} from '@google/generative-ai';\nimport type {\n  GenerateContentRequest,\n  SafetySetting,\n  ToolConfig,\n} from '@google/generative-ai';\nimport type { CallbackManagerForLLMRun } from '@langchain/core/callbacks/manager';\nimport type { BaseMessage, UsageMetadata } from '@langchain/core/messages';\nimport type { GeminiApiUsageMetadata, InputTokenDetails } from './types';\nimport type { GoogleClientOptions, GoogleThinkingConfig } from '@/types';\nimport {\n  convertResponseContentToChatGenerationChunk,\n  convertBaseMessagesToContent,\n  mapGenerateContentResultToChatResult,\n} from './utils/common';\n\ntype GoogleToolConfigWithServerSideInvocations = ToolConfig & {\n  includeServerSideToolInvocations?: boolean;\n  functionCallingConfig?: Omit<\n    NonNullable<ToolConfig['functionCallingConfig']>,\n    'mode'\n  > & {\n    mode?:\n      | NonNullable<ToolConfig['functionCallingConfig']>['mode']\n      | 'VALIDATED';\n  };\n};\n\nexport class CustomChatGoogleGenerativeAI extends ChatGoogleGenerativeAI {\n  thinkingConfig?: GoogleThinkingConfig;\n  includeServerSideToolInvocations?: boolean;\n\n  /**\n   * Override to add gemini-3 model support for multimodal and function calling thought signatures\n   */\n  get _isMultimodalModel(): boolean {\n    return (\n      this.model.startsWith('gemini-1.5') ||\n      this.model.startsWith('gemini-2') ||\n      (this.model.startsWith('gemma-3-') &&\n        !this.model.startsWith('gemma-3-1b')) ||\n      this.model.startsWith('gemini-3')\n    );\n  }\n\n  constructor(fields: GoogleClientOptions) {\n    super(fields);\n\n    this.model = fields.model.replace(/^models\\//, '');\n\n    this.maxOutputTokens = fields.maxOutputTokens ?? this.maxOutputTokens;\n\n    if (this.maxOutputTokens != null && this.maxOutputTokens < 0) {\n      throw new Error('`maxOutputTokens` must be a positive integer');\n    }\n\n    this.temperature = fields.temperature ?? this.temperature;\n    if (\n      this.temperature != null &&\n      (this.temperature < 0 || this.temperature > 2)\n    ) {\n      throw new Error('`temperature` must be in the range of [0.0,2.0]');\n    }\n\n    this.topP = fields.topP ?? this.topP;\n    if (this.topP != null && this.topP < 0) {\n      throw new Error('`topP` must be a positive integer');\n    }\n\n    if (this.topP != null && this.topP > 1) {\n      throw new Error('`topP` must be below 1.');\n    }\n\n    this.topK = fields.topK ?? this.topK;\n    if (this.topK != null && this.topK < 0) {\n      throw new Error('`topK` must be a positive integer');\n    }\n\n    this.stopSequences = fields.stopSequences ?? this.stopSequences;\n\n    this.apiKey = fields.apiKey ?? getEnvironmentVariable('GOOGLE_API_KEY');\n    if (this.apiKey == null || this.apiKey === '') {\n      throw new Error(\n        'Please set an API key for Google GenerativeAI ' +\n          'in the environment variable GOOGLE_API_KEY ' +\n          'or in the `apiKey` field of the ' +\n          'ChatGoogleGenerativeAI constructor'\n      );\n    }\n\n    this.safetySettings = fields.safetySettings ?? this.safetySettings;\n    if (this.safetySettings && this.safetySettings.length > 0) {\n      const safetySettingsSet = new Set(\n        this.safetySettings.map((s) => s.category)\n      );\n      if (safetySettingsSet.size !== this.safetySettings.length) {\n        throw new Error(\n          'The categories in `safetySettings` array must be unique'\n        );\n      }\n    }\n\n    this.thinkingConfig = fields.thinkingConfig ?? this.thinkingConfig;\n    this.includeServerSideToolInvocations =\n      fields.includeServerSideToolInvocations ??\n      this.includeServerSideToolInvocations;\n\n    this.streaming = fields.streaming ?? this.streaming;\n    this.json = fields.json;\n\n    // @ts-ignore - Accessing private property from parent class\n    this.client = new GenerativeAI(this.apiKey).getGenerativeModel(\n      {\n        model: this.model,\n        safetySettings: this.safetySettings as SafetySetting[],\n        generationConfig: {\n          stopSequences: this.stopSequences,\n          maxOutputTokens: this.maxOutputTokens,\n          temperature: this.temperature,\n          topP: this.topP,\n          topK: this.topK,\n          ...(this.json != null\n            ? { responseMimeType: 'application/json' }\n            : {}),\n        },\n      },\n      {\n        apiVersion: fields.apiVersion,\n        baseUrl: fields.baseUrl,\n        customHeaders: fields.customHeaders,\n      }\n    );\n    this.streamUsage = fields.streamUsage ?? this.streamUsage;\n  }\n\n  static lc_name(): 'LibreChatGoogleGenerativeAI' {\n    return 'LibreChatGoogleGenerativeAI';\n  }\n\n  /**\n   * Helper function to convert Gemini API usage metadata to LangChain format\n   * Includes support for cached tokens and tier-based tracking for gemini-3-pro-preview\n   */\n  private _convertToUsageMetadata(\n    usageMetadata: GeminiApiUsageMetadata | undefined,\n    model: string\n  ): UsageMetadata | undefined {\n    if (!usageMetadata) {\n      return undefined;\n    }\n\n    const output: UsageMetadata = {\n      input_tokens: usageMetadata.promptTokenCount ?? 0,\n      output_tokens:\n        (usageMetadata.candidatesTokenCount ?? 0) +\n        (usageMetadata.thoughtsTokenCount ?? 0),\n      total_tokens: usageMetadata.totalTokenCount ?? 0,\n    };\n\n    if (usageMetadata.cachedContentTokenCount) {\n      output.input_token_details ??= {};\n      output.input_token_details.cache_read =\n        usageMetadata.cachedContentTokenCount;\n    }\n\n    // gemini-3-pro-preview has bracket based tracking of tokens per request\n    if (model === 'gemini-3-pro-preview') {\n      const over200k = Math.max(\n        0,\n        (usageMetadata.promptTokenCount ?? 0) - 200000\n      );\n      const cachedOver200k = Math.max(\n        0,\n        (usageMetadata.cachedContentTokenCount ?? 0) - 200000\n      );\n      if (over200k) {\n        output.input_token_details = {\n          ...output.input_token_details,\n          over_200k: over200k,\n        } as InputTokenDetails;\n      }\n      if (cachedOver200k) {\n        output.input_token_details = {\n          ...output.input_token_details,\n          cache_read_over_200k: cachedOver200k,\n        } as InputTokenDetails;\n      }\n    }\n\n    return output;\n  }\n\n  invocationParams(\n    options?: this['ParsedCallOptions']\n  ): Omit<GenerateContentRequest, 'contents'> {\n    const params = super.invocationParams(options);\n    if (this.thinkingConfig) {\n      /** @ts-ignore */\n      this.client.generationConfig = {\n        /** @ts-ignore */\n        ...this.client.generationConfig,\n        /** @ts-ignore */\n        thinkingConfig: this.thinkingConfig,\n      };\n    }\n    if (\n      this.includeServerSideToolInvocations === true &&\n      Array.isArray(params.tools) &&\n      params.tools.length > 0\n    ) {\n      const toolConfig = params.toolConfig as\n        | GoogleToolConfigWithServerSideInvocations\n        | undefined;\n      const functionCallingConfig = toolConfig?.functionCallingConfig;\n      params.toolConfig = {\n        ...toolConfig,\n        ...(functionCallingConfig?.mode === FunctionCallingMode.AUTO\n          ? {\n            functionCallingConfig: {\n              ...functionCallingConfig,\n              mode: 'VALIDATED',\n            },\n          }\n          : {}),\n        includeServerSideToolInvocations: true,\n      } as ToolConfig;\n    }\n    return params;\n  }\n\n  async _generate(\n    messages: BaseMessage[],\n    options: this['ParsedCallOptions'],\n    runManager?: CallbackManagerForLLMRun\n  ): Promise<import('@langchain/core/outputs').ChatResult> {\n    const prompt = convertBaseMessagesToContent(\n      messages,\n      this._isMultimodalModel,\n      this.useSystemInstruction,\n      this.model\n    );\n    let actualPrompt = prompt;\n    if (prompt?.[0].role === 'system') {\n      const [systemInstruction] = prompt;\n      /** @ts-ignore */\n      this.client.systemInstruction = systemInstruction;\n      actualPrompt = prompt.slice(1);\n    }\n    const parameters = this.invocationParams(options);\n    const request = {\n      ...parameters,\n      contents: actualPrompt,\n    };\n\n    const res = await this.caller.callWithOptions(\n      { signal: options.signal },\n      async () =>\n        /** @ts-ignore */\n        this.client.generateContent(request)\n    );\n\n    const response = res.response;\n    const usageMetadata = this._convertToUsageMetadata(\n      /** @ts-ignore */\n      response.usageMetadata,\n      this.model\n    );\n\n    /** @ts-ignore */\n    const generationResult = mapGenerateContentResultToChatResult(response, {\n      usageMetadata,\n    });\n\n    await runManager?.handleLLMNewToken(\n      generationResult.generations[0].text || '',\n      undefined,\n      undefined,\n      undefined,\n      undefined,\n      undefined\n    );\n    return generationResult;\n  }\n\n  async *_streamResponseChunks(\n    messages: BaseMessage[],\n    options: this['ParsedCallOptions'],\n    runManager?: CallbackManagerForLLMRun\n  ): AsyncGenerator<ChatGenerationChunk> {\n    const prompt = convertBaseMessagesToContent(\n      messages,\n      this._isMultimodalModel,\n      this.useSystemInstruction,\n      this.model\n    );\n    let actualPrompt = prompt;\n    if (prompt?.[0].role === 'system') {\n      const [systemInstruction] = prompt;\n      /** @ts-ignore */\n      this.client.systemInstruction = systemInstruction;\n      actualPrompt = prompt.slice(1);\n    }\n    const parameters = this.invocationParams(options);\n    const request = {\n      ...parameters,\n      contents: actualPrompt,\n    };\n    const stream = await this.caller.callWithOptions(\n      { signal: options.signal },\n      async () => {\n        /** @ts-ignore */\n        const { stream } = await this.client.generateContentStream(request);\n        return stream;\n      }\n    );\n\n    let index = 0;\n    let lastUsageMetadata: UsageMetadata | undefined;\n    for await (const response of stream) {\n      if (\n        'usageMetadata' in response &&\n        this.streamUsage !== false &&\n        options.streamUsage !== false\n      ) {\n        lastUsageMetadata = this._convertToUsageMetadata(\n          response.usageMetadata as GeminiApiUsageMetadata | undefined,\n          this.model\n        );\n      }\n\n      const chunk = convertResponseContentToChatGenerationChunk(response, {\n        usageMetadata: undefined,\n        index,\n      });\n      index += 1;\n      if (!chunk) {\n        continue;\n      }\n\n      yield chunk;\n      await runManager?.handleLLMNewToken(\n        chunk.text || '',\n        undefined,\n        undefined,\n        undefined,\n        undefined,\n        { chunk }\n      );\n    }\n\n    if (lastUsageMetadata) {\n      const finalChunk = new ChatGenerationChunk({\n        text: '',\n        message: new AIMessageChunk({\n          content: '',\n          usage_metadata: lastUsageMetadata,\n        }),\n      });\n      yield finalChunk;\n      await runManager?.handleLLMNewToken(\n        finalChunk.text || '',\n        undefined,\n        undefined,\n        undefined,\n        undefined,\n        { chunk: finalChunk }\n      );\n    }\n  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+{"version":3,"file":"index.cjs","names":["ChatGoogleGenerativeAI","GenerativeAI","FunctionCallingMode","convertBaseMessagesToContent","dropUnsupportedModelTurnPrefill","mapGenerateContentResultToChatResult","convertResponseContentToChatGenerationChunk","ChatGenerationChunk","AIMessageChunk"],"sources":["../../../../src/llm/google/index.ts"],"sourcesContent":["/* eslint-disable @typescript-eslint/ban-ts-comment */\nimport { AIMessageChunk } from '@langchain/core/messages';\nimport { ChatGenerationChunk } from '@langchain/core/outputs';\nimport { ChatGoogleGenerativeAI } from '@langchain/google-genai';\nimport { getEnvironmentVariable } from '@langchain/core/utils/env';\nimport {\n  FunctionCallingMode,\n  GoogleGenerativeAI as GenerativeAI,\n} from '@google/generative-ai';\nimport type {\n  GenerateContentRequest,\n  SafetySetting,\n  ToolConfig,\n} from '@google/generative-ai';\nimport type { CallbackManagerForLLMRun } from '@langchain/core/callbacks/manager';\nimport type { BaseMessage, UsageMetadata } from '@langchain/core/messages';\nimport type { GeminiApiUsageMetadata, InputTokenDetails } from './types';\nimport type { GoogleClientOptions, GoogleThinkingConfig } from '@/types';\nimport {\n  convertResponseContentToChatGenerationChunk,\n  convertBaseMessagesToContent,\n  dropUnsupportedModelTurnPrefill,\n  mapGenerateContentResultToChatResult,\n} from './utils/common';\n\ntype GoogleToolConfigWithServerSideInvocations = ToolConfig & {\n  includeServerSideToolInvocations?: boolean;\n  functionCallingConfig?: Omit<\n    NonNullable<ToolConfig['functionCallingConfig']>,\n    'mode'\n  > & {\n    mode?:\n      | NonNullable<ToolConfig['functionCallingConfig']>['mode']\n      | 'VALIDATED';\n  };\n};\n\nexport class CustomChatGoogleGenerativeAI extends ChatGoogleGenerativeAI {\n  thinkingConfig?: GoogleThinkingConfig;\n  includeServerSideToolInvocations?: boolean;\n\n  /**\n   * Override to add gemini-3 model support for multimodal and function calling thought signatures\n   */\n  get _isMultimodalModel(): boolean {\n    return (\n      this.model.startsWith('gemini-1.5') ||\n      this.model.startsWith('gemini-2') ||\n      (this.model.startsWith('gemma-3-') &&\n        !this.model.startsWith('gemma-3-1b')) ||\n      this.model.startsWith('gemini-3')\n    );\n  }\n\n  constructor(fields: GoogleClientOptions) {\n    super(fields);\n\n    this.model = fields.model.replace(/^models\\//, '');\n\n    this.maxOutputTokens = fields.maxOutputTokens ?? this.maxOutputTokens;\n\n    if (this.maxOutputTokens != null && this.maxOutputTokens < 0) {\n      throw new Error('`maxOutputTokens` must be a positive integer');\n    }\n\n    this.temperature = fields.temperature ?? this.temperature;\n    if (\n      this.temperature != null &&\n      (this.temperature < 0 || this.temperature > 2)\n    ) {\n      throw new Error('`temperature` must be in the range of [0.0,2.0]');\n    }\n\n    this.topP = fields.topP ?? this.topP;\n    if (this.topP != null && this.topP < 0) {\n      throw new Error('`topP` must be a positive integer');\n    }\n\n    if (this.topP != null && this.topP > 1) {\n      throw new Error('`topP` must be below 1.');\n    }\n\n    this.topK = fields.topK ?? this.topK;\n    if (this.topK != null && this.topK < 0) {\n      throw new Error('`topK` must be a positive integer');\n    }\n\n    this.stopSequences = fields.stopSequences ?? this.stopSequences;\n\n    this.apiKey = fields.apiKey ?? getEnvironmentVariable('GOOGLE_API_KEY');\n    if (this.apiKey == null || this.apiKey === '') {\n      throw new Error(\n        'Please set an API key for Google GenerativeAI ' +\n          'in the environment variable GOOGLE_API_KEY ' +\n          'or in the `apiKey` field of the ' +\n          'ChatGoogleGenerativeAI constructor'\n      );\n    }\n\n    this.safetySettings = fields.safetySettings ?? this.safetySettings;\n    if (this.safetySettings && this.safetySettings.length > 0) {\n      const safetySettingsSet = new Set(\n        this.safetySettings.map((s) => s.category)\n      );\n      if (safetySettingsSet.size !== this.safetySettings.length) {\n        throw new Error(\n          'The categories in `safetySettings` array must be unique'\n        );\n      }\n    }\n\n    this.thinkingConfig = fields.thinkingConfig ?? this.thinkingConfig;\n    this.includeServerSideToolInvocations =\n      fields.includeServerSideToolInvocations ??\n      this.includeServerSideToolInvocations;\n\n    this.streaming = fields.streaming ?? this.streaming;\n    this.json = fields.json;\n\n    // @ts-ignore - Accessing private property from parent class\n    this.client = new GenerativeAI(this.apiKey).getGenerativeModel(\n      {\n        model: this.model,\n        safetySettings: this.safetySettings as SafetySetting[],\n        generationConfig: {\n          stopSequences: this.stopSequences,\n          maxOutputTokens: this.maxOutputTokens,\n          temperature: this.temperature,\n          topP: this.topP,\n          topK: this.topK,\n          ...(this.json != null\n            ? { responseMimeType: 'application/json' }\n            : {}),\n        },\n      },\n      {\n        apiVersion: fields.apiVersion,\n        baseUrl: fields.baseUrl,\n        customHeaders: fields.customHeaders,\n      }\n    );\n    this.streamUsage = fields.streamUsage ?? this.streamUsage;\n  }\n\n  static lc_name(): 'LibreChatGoogleGenerativeAI' {\n    return 'LibreChatGoogleGenerativeAI';\n  }\n\n  /**\n   * Helper function to convert Gemini API usage metadata to LangChain format\n   * Includes support for cached tokens and tier-based tracking for gemini-3-pro-preview\n   */\n  private _convertToUsageMetadata(\n    usageMetadata: GeminiApiUsageMetadata | undefined,\n    model: string\n  ): UsageMetadata | undefined {\n    if (!usageMetadata) {\n      return undefined;\n    }\n\n    const output: UsageMetadata = {\n      input_tokens: usageMetadata.promptTokenCount ?? 0,\n      output_tokens:\n        (usageMetadata.candidatesTokenCount ?? 0) +\n        (usageMetadata.thoughtsTokenCount ?? 0),\n      total_tokens: usageMetadata.totalTokenCount ?? 0,\n    };\n\n    if (usageMetadata.cachedContentTokenCount) {\n      output.input_token_details ??= {};\n      output.input_token_details.cache_read =\n        usageMetadata.cachedContentTokenCount;\n    }\n\n    // gemini-3-pro-preview has bracket based tracking of tokens per request\n    if (model === 'gemini-3-pro-preview') {\n      const over200k = Math.max(\n        0,\n        (usageMetadata.promptTokenCount ?? 0) - 200000\n      );\n      const cachedOver200k = Math.max(\n        0,\n        (usageMetadata.cachedContentTokenCount ?? 0) - 200000\n      );\n      if (over200k) {\n        output.input_token_details = {\n          ...output.input_token_details,\n          over_200k: over200k,\n        } as InputTokenDetails;\n      }\n      if (cachedOver200k) {\n        output.input_token_details = {\n          ...output.input_token_details,\n          cache_read_over_200k: cachedOver200k,\n        } as InputTokenDetails;\n      }\n    }\n\n    return output;\n  }\n\n  invocationParams(\n    options?: this['ParsedCallOptions']\n  ): Omit<GenerateContentRequest, 'contents'> {\n    const params = super.invocationParams(options);\n    if (this.thinkingConfig) {\n      /** @ts-ignore */\n      this.client.generationConfig = {\n        /** @ts-ignore */\n        ...this.client.generationConfig,\n        /** @ts-ignore */\n        thinkingConfig: this.thinkingConfig,\n      };\n    }\n    if (\n      this.includeServerSideToolInvocations === true &&\n      Array.isArray(params.tools) &&\n      params.tools.length > 0\n    ) {\n      const toolConfig = params.toolConfig as\n        | GoogleToolConfigWithServerSideInvocations\n        | undefined;\n      const functionCallingConfig = toolConfig?.functionCallingConfig;\n      params.toolConfig = {\n        ...toolConfig,\n        ...(functionCallingConfig?.mode === FunctionCallingMode.AUTO\n          ? {\n            functionCallingConfig: {\n              ...functionCallingConfig,\n              mode: 'VALIDATED',\n            },\n          }\n          : {}),\n        includeServerSideToolInvocations: true,\n      } as ToolConfig;\n    }\n    return params;\n  }\n\n  async _generate(\n    messages: BaseMessage[],\n    options: this['ParsedCallOptions'],\n    runManager?: CallbackManagerForLLMRun\n  ): Promise<import('@langchain/core/outputs').ChatResult> {\n    const prompt = convertBaseMessagesToContent(\n      messages,\n      this._isMultimodalModel,\n      this.useSystemInstruction,\n      this.model\n    );\n    let actualPrompt = prompt;\n    if (prompt?.[0].role === 'system') {\n      const [systemInstruction] = prompt;\n      /** @ts-ignore */\n      this.client.systemInstruction = systemInstruction;\n      actualPrompt = prompt.slice(1);\n    }\n    actualPrompt = dropUnsupportedModelTurnPrefill(actualPrompt, this.model);\n    const parameters = this.invocationParams(options);\n    const request = {\n      ...parameters,\n      contents: actualPrompt,\n    };\n\n    const res = await this.caller.callWithOptions(\n      { signal: options.signal },\n      async () =>\n        /** @ts-ignore */\n        this.client.generateContent(request)\n    );\n\n    const response = res.response;\n    const usageMetadata = this._convertToUsageMetadata(\n      /** @ts-ignore */\n      response.usageMetadata,\n      this.model\n    );\n\n    /** @ts-ignore */\n    const generationResult = mapGenerateContentResultToChatResult(response, {\n      usageMetadata,\n    });\n\n    await runManager?.handleLLMNewToken(\n      generationResult.generations[0].text || '',\n      undefined,\n      undefined,\n      undefined,\n      undefined,\n      undefined\n    );\n    return generationResult;\n  }\n\n  async *_streamResponseChunks(\n    messages: BaseMessage[],\n    options: this['ParsedCallOptions'],\n    runManager?: CallbackManagerForLLMRun\n  ): AsyncGenerator<ChatGenerationChunk> {\n    const prompt = convertBaseMessagesToContent(\n      messages,\n      this._isMultimodalModel,\n      this.useSystemInstruction,\n      this.model\n    );\n    let actualPrompt = prompt;\n    if (prompt?.[0].role === 'system') {\n      const [systemInstruction] = prompt;\n      /** @ts-ignore */\n      this.client.systemInstruction = systemInstruction;\n      actualPrompt = prompt.slice(1);\n    }\n    actualPrompt = dropUnsupportedModelTurnPrefill(actualPrompt, this.model);\n    const parameters = this.invocationParams(options);\n    const request = {\n      ...parameters,\n      contents: actualPrompt,\n    };\n    const stream = await this.caller.callWithOptions(\n      { signal: options.signal },\n      async () => {\n        /** @ts-ignore */\n        const { stream } = await this.client.generateContentStream(request);\n        return stream;\n      }\n    );\n\n    let index = 0;\n    let lastUsageMetadata: UsageMetadata | undefined;\n    for await (const response of stream) {\n      if (\n        'usageMetadata' in response &&\n        this.streamUsage !== false &&\n        options.streamUsage !== false\n      ) {\n        lastUsageMetadata = this._convertToUsageMetadata(\n          response.usageMetadata as GeminiApiUsageMetadata | undefined,\n          this.model\n        );\n      }\n\n      const chunk = convertResponseContentToChatGenerationChunk(response, {\n        usageMetadata: undefined,\n        index,\n      });\n      index += 1;\n      if (!chunk) {\n        continue;\n      }\n\n      yield chunk;\n      await runManager?.handleLLMNewToken(\n        chunk.text || '',\n        undefined,\n        undefined,\n        undefined,\n        undefined,\n        { chunk }\n      );\n    }\n\n    if (lastUsageMetadata) {\n      const finalChunk = new ChatGenerationChunk({\n        text: '',\n        message: new AIMessageChunk({\n          content: '',\n          usage_metadata: lastUsageMetadata,\n        }),\n      });\n      yield finalChunk;\n      await runManager?.handleLLMNewToken(\n        finalChunk.text || '',\n        undefined,\n        undefined,\n        undefined,\n        undefined,\n        { chunk: finalChunk }\n      );\n    }\n  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package/dist/cjs/llm/google/utils/common.cjs

@@ -277,6 +277,33 @@ function convertBaseMessagesToContent(messages, isMultimodalModel, convertSystem
 		mergeWithPreviousContent: false
 	}).content;
 }
+/**
+* Gemini models that reject a request whose `contents` end with a `model`-role
+* turn (a "prefill"). Google enforces this on newer generations (Gemini 3.6
+* Flash, Gemini 3.5 Flash-Lite) while older/sibling models still accept a
+* trailing model turn, so the rule is model-scoped rather than version-wide.
+* Extend this list as Google applies the restriction to further models.
+* @see https://ai.google.dev/gemini-api/docs/latest-model#api-changes-and-parameter-updates
+*/
+const NO_PREFILL_GEMINI_MODELS = ["gemini-3.6-flash", "gemini-3.5-flash-lite"];
+function rejectsModelTurnPrefill(model) {
+	if (model == null || model === "") return false;
+	const modelId = model.toLowerCase().split("/").pop() ?? "";
+	return NO_PREFILL_GEMINI_MODELS.some((id) => modelId === id || modelId.startsWith(`${id}-`));
+}
+/**
+* Drops trailing `model`-role turns for models that reject prefill (see
+* {@link rejectsModelTurnPrefill}). Such a turn is only produced by prefill
+* flows (e.g. editing an assistant reply and resubmitting); these models return
+* HTTP 400 for it, so we drop it and let the model generate fresh from the
+* preceding user turn. No-op for every other model, preserving working prefill.
+*/
+function dropUnsupportedModelTurnPrefill(contents, model) {
+	if (contents == null || contents.length === 0 || !rejectsModelTurnPrefill(model)) return contents;
+	let end = contents.length;
+	while (end > 1 && contents[end - 1]?.role === "model") end -= 1;
+	return end === contents.length ? contents : contents.slice(0, end);
+}
 function convertResponseContentToChatGenerationChunk(response, extra) {
 	if (!response.candidates || response.candidates.length === 0) return null;
 	const [candidate] = response.candidates;
@@ -434,6 +461,7 @@ function mapGenerateContentResultToChatResult(response, extra) {
 //#endregion
 exports.convertBaseMessagesToContent = convertBaseMessagesToContent;
 exports.convertResponseContentToChatGenerationChunk = convertResponseContentToChatGenerationChunk;
+exports.dropUnsupportedModelTurnPrefill = dropUnsupportedModelTurnPrefill;
 exports.mapGenerateContentResultToChatResult = mapGenerateContentResultToChatResult;
 
 //# sourceMappingURL=common.cjs.map

package/dist/cjs/llm/google/utils/common.cjs.map

@@ -1 +1 @@
-{"version":3,"file":"common.cjs","names":["ChatMessage","toLangChainContent","STREAMED_TOOL_CALL_ADAPTER_METADATA_KEY","GOOGLE_STREAMED_TOOL_CALL_ADAPTER","STREAMED_TOOL_CALL_SEAL_METADATA_KEY","ChatGenerationChunk","AIMessageChunk","AIMessage"],"sources":["../../../../../src/llm/google/utils/common.ts"],"sourcesContent":["import { v4 as uuidv4 } from 'uuid';\nimport { ChatGenerationChunk } from '@langchain/core/outputs';\nimport { ToolCallChunk } from '@langchain/core/messages/tool';\nimport { isOpenAITool } from '@langchain/core/language_models/base';\nimport { isLangChainTool } from '@langchain/core/utils/function_calling';\nimport {\n  AIMessage,\n  AIMessageChunk,\n  BaseMessage,\n  ChatMessage,\n  ToolMessage,\n  ToolMessageChunk,\n  MessageContent,\n  MessageContentComplex,\n  UsageMetadata,\n  isAIMessage,\n  isBaseMessage,\n  isToolMessage,\n  StandardContentBlockConverter,\n  parseBase64DataUrl,\n  convertToProviderContentBlock,\n  isDataContentBlock,\n} from '@langchain/core/messages';\nimport {\n  POSSIBLE_ROLES,\n  type Part,\n  type Content,\n  type TextPart,\n  type FileDataPart,\n  type InlineDataPart,\n  type FunctionCallPart,\n  type GenerateContentCandidate,\n  type EnhancedGenerateContentResponse,\n  type FunctionDeclaration as GenerativeAIFunctionDeclaration,\n  type FunctionDeclarationsTool as GoogleGenerativeAIFunctionDeclarationsTool,\n} from '@google/generative-ai';\nimport type { ChatGeneration, ChatResult } from '@langchain/core/outputs';\nimport {\n  STREAMED_TOOL_CALL_SEAL_METADATA_KEY,\n  STREAMED_TOOL_CALL_ADAPTER_METADATA_KEY,\n  GOOGLE_STREAMED_TOOL_CALL_ADAPTER,\n} from '@/tools/streamedToolCallSeals';\nimport {\n  jsonSchemaToGeminiParameters,\n  schemaToGenerativeAIParameters,\n} from './zod_to_genai_parameters';\nimport { toLangChainContent } from '@/messages/langchain';\nimport { GoogleGenerativeAIToolType } from '../types';\n\nexport const _FUNCTION_CALL_THOUGHT_SIGNATURES_MAP_KEY =\n  '__gemini_function_call_thought_signatures__';\n\nconst DUMMY_SIGNATURE =\n  'ErYCCrMCAdHtim9kOoOkrPiCNVsmlpMIKd7ZMxgiFbVQOkgp7nlLcDMzVsZwIzvuT7nQROivoXA72ccC2lSDvR0Gh7dkWaGuj7ctv6t7ZceHnecx0QYa+ix8tYpRfjhyWozQ49lWiws6+YGjCt10KRTyWsZ2h6O7iHTYJwKIRwGUHRKy/qK/6kFxJm5ML00gLq4D8s5Z6DBpp2ZlR+uF4G8jJgeWQgyHWVdx2wGYElaceVAc66tZdPQRdOHpWtgYSI1YdaXgVI8KHY3/EfNc2YqqMIulvkDBAnuMhkAjV9xmBa54Tq+ih3Im4+r3DzqhGqYdsSkhS0kZMwte4Hjs65dZzCw9lANxIqYi1DJ639WNPYihp/DCJCos7o+/EeSPJaio5sgWDyUnMGkY1atsJZ+m7pj7DD5tvQ==';\n\ntype GoogleServerSideToolPart = Part & {\n  type?: 'toolCall' | 'toolResponse';\n  toolCall?: object;\n  toolResponse?: object;\n};\n\ntype GoogleServerSideToolPartMetadata = {\n  thought?: boolean;\n  thoughtSignature?: string;\n};\n\ntype GoogleFunctionCallWithId = FunctionCallPart['functionCall'] & {\n  id?: string;\n};\n\ntype GoogleFunctionResponseWithId = {\n  name: string;\n  response: object;\n  id?: string;\n};\n\nfunction getGoogleFunctionId(id?: string): string | undefined {\n  return id != null && id !== '' ? id : undefined;\n}\n\nfunction createGoogleFunctionResponsePart({\n  name,\n  response,\n  id,\n}: {\n  name: string;\n  response: object;\n  id?: string;\n}): Part {\n  const functionId = getGoogleFunctionId(id);\n  const functionResponse: GoogleFunctionResponseWithId = {\n    name,\n    response,\n    ...(functionId != null ? { id: functionId } : {}),\n  };\n  return { functionResponse };\n}\n\n/**\n * Executes a function immediately and returns its result.\n * Functional utility similar to an Immediately Invoked Function Expression (IIFE).\n * @param fn The function to execute.\n * @returns The result of invoking fn.\n */\nexport const iife = <T>(fn: () => T): T => fn();\n\nexport function getMessageAuthor(message: BaseMessage): string {\n  const type = message._getType();\n  if (ChatMessage.isInstance(message)) {\n    return message.role;\n  }\n  if (type === 'tool') {\n    return type;\n  }\n  return message.name ?? type;\n}\n\n/**\n * Maps a message type to a Google Generative AI chat author.\n * @param message The message to map.\n * @param model The model to use for mapping.\n * @returns The message type mapped to a Google Generative AI chat author.\n */\nexport function convertAuthorToRole(\n  author: string\n): (typeof POSSIBLE_ROLES)[number] {\n  switch (author) {\n  /**\n     *  Note: Gemini currently is not supporting system messages\n     *  we will convert them to human messages and merge with following\n     * */\n  case 'supervisor':\n  case 'ai':\n  case 'model': // getMessageAuthor returns message.name. code ex.: return message.name ?? type;\n    return 'model';\n  case 'system':\n    return 'system';\n  case 'human':\n    return 'user';\n  case 'tool':\n  case 'function':\n    return 'function';\n  default:\n    throw new Error(`Unknown / unsupported author: ${author}`);\n  }\n}\n\nfunction messageContentMedia(content: MessageContentComplex): Part {\n  if ('mimeType' in content && 'data' in content) {\n    return {\n      inlineData: {\n        mimeType: content.mimeType,\n        data: content.data,\n      },\n    };\n  }\n  if ('mimeType' in content && 'fileUri' in content) {\n    return {\n      fileData: {\n        mimeType: content.mimeType,\n        fileUri: content.fileUri,\n      },\n    };\n  }\n\n  throw new Error('Invalid media content');\n}\n\nfunction isGoogleServerSideToolPart(\n  content: MessageContentComplex\n): content is MessageContentComplex & GoogleServerSideToolPart {\n  return (\n    'toolCall' in content ||\n    'toolResponse' in content ||\n    content.type === 'toolCall' ||\n    content.type === 'toolResponse'\n  );\n}\n\nfunction convertGoogleServerSideToolPart(\n  content: MessageContentComplex & GoogleServerSideToolPart\n): Part {\n  const metadata: GoogleServerSideToolPartMetadata = {};\n  if ('thought' in content && typeof content.thought === 'boolean') {\n    metadata.thought = content.thought;\n  }\n  if (\n    'thoughtSignature' in content &&\n    typeof content.thoughtSignature === 'string'\n  ) {\n    metadata.thoughtSignature = content.thoughtSignature;\n  }\n  if ('toolCall' in content && content.toolCall != null) {\n    return { toolCall: content.toolCall, ...metadata } as unknown as Part;\n  }\n  if ('toolResponse' in content && content.toolResponse != null) {\n    return {\n      toolResponse: content.toolResponse,\n      ...metadata,\n    } as unknown as Part;\n  }\n\n  return content as Part;\n}\n\nfunction convertGoogleServerSideToolResponsePart(\n  part: Part\n): GoogleServerSideToolPart | undefined {\n  if (\n    'toolCall' in part &&\n    typeof part.toolCall === 'object' &&\n    part.toolCall != null\n  ) {\n    return { ...part, type: 'toolCall', toolCall: part.toolCall };\n  }\n  if (\n    'toolResponse' in part &&\n    typeof part.toolResponse === 'object' &&\n    part.toolResponse != null\n  ) {\n    return { ...part, type: 'toolResponse', toolResponse: part.toolResponse };\n  }\n  return undefined;\n}\n\nfunction inferToolNameFromPreviousMessages(\n  message: ToolMessage | ToolMessageChunk,\n  previousMessages: BaseMessage[]\n): string | undefined {\n  return previousMessages\n    .map((msg) => {\n      if (isAIMessage(msg)) {\n        return msg.tool_calls ?? [];\n      }\n      return [];\n    })\n    .flat()\n    .find((toolCall) => {\n      return toolCall.id === message.tool_call_id;\n    })?.name;\n}\n\nfunction _getStandardContentBlockConverter(\n  isMultimodalModel: boolean\n): StandardContentBlockConverter<{\n  text: TextPart;\n  image: FileDataPart | InlineDataPart;\n  audio: FileDataPart | InlineDataPart;\n  file: FileDataPart | InlineDataPart | TextPart;\n}> {\n  const standardContentBlockConverter: StandardContentBlockConverter<{\n    text: TextPart;\n    image: FileDataPart | InlineDataPart;\n    audio: FileDataPart | InlineDataPart;\n    file: FileDataPart | InlineDataPart | TextPart;\n  }> = {\n    providerName: 'Google Gemini',\n\n    fromStandardTextBlock(block) {\n      return {\n        text: block.text,\n      };\n    },\n\n    fromStandardImageBlock(block): FileDataPart | InlineDataPart {\n      if (!isMultimodalModel) {\n        throw new Error('This model does not support images');\n      }\n      if (block.source_type === 'url') {\n        const data = parseBase64DataUrl({ dataUrl: block.url });\n        if (data) {\n          return {\n            inlineData: {\n              mimeType: data.mime_type,\n              data: data.data,\n            },\n          };\n        } else {\n          return {\n            fileData: {\n              mimeType: block.mime_type ?? '',\n              fileUri: block.url,\n            },\n          };\n        }\n      }\n\n      if (block.source_type === 'base64') {\n        return {\n          inlineData: {\n            mimeType: block.mime_type ?? '',\n            data: block.data,\n          },\n        };\n      }\n\n      throw new Error(`Unsupported source type: ${block.source_type}`);\n    },\n\n    fromStandardAudioBlock(block): FileDataPart | InlineDataPart {\n      if (!isMultimodalModel) {\n        throw new Error('This model does not support audio');\n      }\n      if (block.source_type === 'url') {\n        const data = parseBase64DataUrl({ dataUrl: block.url });\n        if (data) {\n          return {\n            inlineData: {\n              mimeType: data.mime_type,\n              data: data.data,\n            },\n          };\n        } else {\n          return {\n            fileData: {\n              mimeType: block.mime_type ?? '',\n              fileUri: block.url,\n            },\n          };\n        }\n      }\n\n      if (block.source_type === 'base64') {\n        return {\n          inlineData: {\n            mimeType: block.mime_type ?? '',\n            data: block.data,\n          },\n        };\n      }\n\n      throw new Error(`Unsupported source type: ${block.source_type}`);\n    },\n\n    fromStandardFileBlock(block): FileDataPart | InlineDataPart | TextPart {\n      if (!isMultimodalModel) {\n        throw new Error('This model does not support files');\n      }\n      if (block.source_type === 'text') {\n        return {\n          text: block.text,\n        };\n      }\n      if (block.source_type === 'url') {\n        const data = parseBase64DataUrl({ dataUrl: block.url });\n        if (data) {\n          return {\n            inlineData: {\n              mimeType: data.mime_type,\n              data: data.data,\n            },\n          };\n        } else {\n          return {\n            fileData: {\n              mimeType: block.mime_type ?? '',\n              fileUri: block.url,\n            },\n          };\n        }\n      }\n\n      if (block.source_type === 'base64') {\n        return {\n          inlineData: {\n            mimeType: block.mime_type ?? '',\n            data: block.data,\n          },\n        };\n      }\n      throw new Error(`Unsupported source type: ${block.source_type}`);\n    },\n  };\n  return standardContentBlockConverter;\n}\n\nfunction _convertLangChainContentToPart(\n  content: MessageContentComplex,\n  isMultimodalModel: boolean\n): Part | undefined {\n  if (isDataContentBlock(content)) {\n    return convertToProviderContentBlock(\n      content,\n      _getStandardContentBlockConverter(isMultimodalModel)\n    );\n  }\n\n  if (isGoogleServerSideToolPart(content)) {\n    return convertGoogleServerSideToolPart(content);\n  }\n\n  if (content.type === 'text') {\n    return { text: content.text };\n  } else if (content.type === 'executableCode') {\n    return { executableCode: content.executableCode };\n  } else if (content.type === 'codeExecutionResult') {\n    return { codeExecutionResult: content.codeExecutionResult };\n  } else if (content.type === 'image_url') {\n    if (!isMultimodalModel) {\n      throw new Error('This model does not support images');\n    }\n    let source: string;\n    if (typeof content.image_url === 'string') {\n      source = content.image_url;\n    } else if (\n      typeof content.image_url === 'object' &&\n      'url' in content.image_url\n    ) {\n      source = content.image_url.url;\n    } else {\n      throw new Error('Please provide image as base64 encoded data URL');\n    }\n    const [dm, data] = source.split(',');\n    if (!dm.startsWith('data:')) {\n      throw new Error('Please provide image as base64 encoded data URL');\n    }\n\n    const [mimeType, encoding] = dm.replace(/^data:/, '').split(';');\n    if (encoding !== 'base64') {\n      throw new Error('Please provide image as base64 encoded data URL');\n    }\n\n    return {\n      inlineData: {\n        data,\n        mimeType,\n      },\n    };\n  } else if (content.type === 'media') {\n    return messageContentMedia(content);\n  } else if (content.type === 'tool_use') {\n    return {\n      functionCall: {\n        name: content.name,\n        args: content.input,\n      },\n    };\n  } else if (\n    content.type?.includes('/') === true &&\n    // Ensure it's a single slash.\n    content.type.split('/').length === 2 &&\n    'data' in content &&\n    typeof content.data === 'string'\n  ) {\n    return {\n      inlineData: {\n        mimeType: content.type,\n        data: content.data,\n      },\n    };\n  } else if ('functionCall' in content) {\n    // No action needed here — function calls will be added later from message.tool_calls\n    return undefined;\n  } else {\n    if ('type' in content) {\n      throw new Error(`Unknown content type ${content.type}`);\n    } else {\n      throw new Error(`Unknown content ${JSON.stringify(content)}`);\n    }\n  }\n}\n\nexport function convertMessageContentToParts(\n  message: BaseMessage,\n  isMultimodalModel: boolean,\n  previousMessages: BaseMessage[],\n  model?: string\n): Part[] {\n  if (isToolMessage(message)) {\n    const messageName =\n      message.name ??\n      inferToolNameFromPreviousMessages(message, previousMessages);\n    if (messageName === undefined) {\n      throw new Error(\n        `Google requires a tool name for each tool call response, and we could not infer a called tool name for ToolMessage \"${message.id}\" from your passed messages. Please populate a \"name\" field on that ToolMessage explicitly.`\n      );\n    }\n\n    const result = Array.isArray(message.content)\n      ? (message.content\n        .map((c) => _convertLangChainContentToPart(c, isMultimodalModel))\n        .filter((p) => p !== undefined) as Part[])\n      : message.content;\n\n    if (message.status === 'error') {\n      return [\n        createGoogleFunctionResponsePart({\n          name: messageName,\n          // The API expects an object with an `error` field if the function call fails.\n          // `error` must be a valid object (not a string or array), so we wrap `message.content` here\n          response: { error: { details: result } },\n          id: message.tool_call_id,\n        }),\n      ];\n    }\n\n    return [\n      createGoogleFunctionResponsePart({\n        name: messageName,\n        // again, can't have a string or array value for `response`, so we wrap it as an object here\n        response: { result },\n        id: message.tool_call_id,\n      }),\n    ];\n  }\n\n  let functionCalls: FunctionCallPart[] = [];\n  const messageParts: Part[] = [];\n\n  if (typeof message.content === 'string' && message.content) {\n    messageParts.push({ text: message.content });\n  }\n\n  if (Array.isArray(message.content)) {\n    messageParts.push(\n      ...(message.content\n        .map((c) => _convertLangChainContentToPart(c, isMultimodalModel))\n        .filter((p) => p !== undefined) as Part[])\n    );\n  }\n\n  const functionThoughtSignatures = (\n    message.additional_kwargs as BaseMessage['additional_kwargs'] | undefined\n  )?.[_FUNCTION_CALL_THOUGHT_SIGNATURES_MAP_KEY] as\n    | Record<string, string>\n    | undefined;\n\n  if (isAIMessage(message) && (message.tool_calls?.length ?? 0) > 0) {\n    functionCalls = (message.tool_calls ?? []).map((tc) => {\n      const thoughtSignature = iife(() => {\n        if (tc.id != null && tc.id !== '') {\n          const signature = functionThoughtSignatures?.[tc.id];\n          if (signature != null && signature !== '') {\n            return signature;\n          }\n        }\n        if (model?.includes('gemini-3') === true) {\n          return DUMMY_SIGNATURE;\n        }\n        return '';\n      });\n      const functionId = getGoogleFunctionId(tc.id);\n      const functionCall: GoogleFunctionCallWithId = {\n        name: tc.name,\n        args: tc.args,\n        ...(functionId != null ? { id: functionId } : {}),\n      };\n\n      return {\n        functionCall,\n        ...(thoughtSignature ? { thoughtSignature } : {}),\n      };\n    });\n  }\n\n  return [...messageParts, ...functionCalls];\n}\n\nexport function convertBaseMessagesToContent(\n  messages: BaseMessage[],\n  isMultimodalModel: boolean,\n  convertSystemMessageToHumanContent: boolean = false,\n\n  model?: string\n): Content[] | undefined {\n  return messages.reduce<{\n    content: Content[] | undefined;\n    mergeWithPreviousContent: boolean;\n  }>(\n    (acc, message, index) => {\n      if (!isBaseMessage(message)) {\n        throw new Error('Unsupported message input');\n      }\n      const author = getMessageAuthor(message);\n      if (author === 'system' && index !== 0) {\n        throw new Error('System message should be the first one');\n      }\n      const role = convertAuthorToRole(author);\n\n      const prevContent = acc.content?.[acc.content.length];\n      if (\n        !acc.mergeWithPreviousContent &&\n        prevContent &&\n        prevContent.role === role\n      ) {\n        throw new Error(\n          'Google Generative AI requires alternate messages between authors'\n        );\n      }\n\n      const parts = convertMessageContentToParts(\n        message,\n        isMultimodalModel,\n        messages.slice(0, index),\n        model\n      );\n\n      if (acc.mergeWithPreviousContent) {\n        const prevContent = acc.content?.[acc.content.length - 1];\n        if (!prevContent) {\n          throw new Error(\n            'There was a problem parsing your system message. Please try a prompt without one.'\n          );\n        }\n        prevContent.parts.push(...parts);\n\n        return {\n          mergeWithPreviousContent: false,\n          content: acc.content,\n        };\n      }\n      let actualRole = role;\n      if (\n        actualRole === 'function' ||\n        (actualRole === 'system' && !convertSystemMessageToHumanContent)\n      ) {\n        // GenerativeAI API will throw an error if the role is not \"user\" or \"model.\"\n        actualRole = 'user';\n      }\n      const content: Content = {\n        role: actualRole,\n        parts,\n      };\n      return {\n        mergeWithPreviousContent:\n          author === 'system' && !convertSystemMessageToHumanContent,\n        content: [...(acc.content ?? []), content],\n      };\n    },\n    { content: [], mergeWithPreviousContent: false }\n  ).content;\n}\n\nexport function convertResponseContentToChatGenerationChunk(\n  response: EnhancedGenerateContentResponse,\n  extra: {\n    usageMetadata?: UsageMetadata | undefined;\n    index: number;\n  }\n): ChatGenerationChunk | null {\n  if (!response.candidates || response.candidates.length === 0) {\n    return null;\n  }\n  const [candidate] = response.candidates as [\n    Partial<GenerateContentCandidate> | undefined,\n  ];\n  const { content: candidateContent, ...generationInfo } = candidate ?? {};\n\n  // Extract function calls directly from parts to preserve thoughtSignature\n  const functionCalls =\n    (candidateContent?.parts as Part[] | undefined)?.reduce(\n      (acc, p) => {\n        if ('functionCall' in p && p.functionCall) {\n          acc.push({\n            ...p,\n            id:\n              'id' in p.functionCall && typeof p.functionCall.id === 'string'\n                ? p.functionCall.id\n                : uuidv4(),\n          });\n        }\n        return acc;\n      },\n      [] as (\n        | undefined\n        | (FunctionCallPart & { id: string; thoughtSignature?: string })\n      )[]\n    ) ?? [];\n\n  let content: MessageContent | undefined;\n  // Checks if some parts do not have text. If false, it means that the content is a string.\n  const reasoningParts: string[] = [];\n  if (\n    candidateContent != null &&\n    Array.isArray(candidateContent.parts) &&\n    candidateContent.parts.every((p) => 'text' in p)\n  ) {\n    // content = candidateContent.parts.map((p) => p.text).join('');\n    const textParts: string[] = [];\n    for (const part of candidateContent.parts) {\n      if ('thought' in part && part.thought === true) {\n        reasoningParts.push(part.text ?? '');\n        continue;\n      }\n      textParts.push(part.text ?? '');\n    }\n    content = textParts.join('');\n  } else if (candidateContent && Array.isArray(candidateContent.parts)) {\n    content = toLangChainContent(\n      candidateContent.parts\n        .map((p) => {\n          if ('text' in p && 'thought' in p && p.thought === true) {\n            reasoningParts.push(p.text ?? '');\n            return undefined;\n          } else if ('text' in p) {\n            return {\n              type: 'text',\n              text: p.text,\n            };\n          } else if ('executableCode' in p) {\n            return {\n              type: 'executableCode',\n              executableCode: p.executableCode,\n            };\n          } else if ('codeExecutionResult' in p) {\n            return {\n              type: 'codeExecutionResult',\n              codeExecutionResult: p.codeExecutionResult,\n            };\n          }\n          const serverSideToolPart = convertGoogleServerSideToolResponsePart(p);\n          if (serverSideToolPart !== undefined) {\n            return serverSideToolPart;\n          }\n          return p;\n        })\n        .filter((p) => p !== undefined)\n    );\n  } else {\n    // no content returned - likely due to abnormal stop reason, e.g. malformed function call\n    content = [];\n  }\n\n  let text = '';\n  if (typeof content === 'string' && content) {\n    text = content;\n  } else if (Array.isArray(content)) {\n    const block = content.find((b) => 'text' in b) as\n      | { text: string }\n      | undefined;\n    text = block?.text ?? '';\n  }\n\n  const toolCallChunks: ToolCallChunk[] = [];\n  if (functionCalls.length > 0) {\n    toolCallChunks.push(\n      ...functionCalls.map((fc) => ({\n        type: 'tool_call_chunk' as const,\n        id: fc?.id,\n        name: fc?.functionCall.name,\n        args: JSON.stringify(fc?.functionCall.args),\n      }))\n    );\n  }\n\n  // Extract thought signatures from function calls for Gemini 3+\n  const functionThoughtSignatures = functionCalls.reduce(\n    (acc, fc) => {\n      if (\n        fc &&\n        'thoughtSignature' in fc &&\n        typeof fc.thoughtSignature === 'string'\n      ) {\n        acc[fc.id] = fc.thoughtSignature;\n      }\n      return acc;\n    },\n    {} as Record<string, string>\n  );\n\n  const additional_kwargs: ChatGeneration['message']['additional_kwargs'] = {\n    [_FUNCTION_CALL_THOUGHT_SIGNATURES_MAP_KEY]: functionThoughtSignatures,\n  };\n\n  if (reasoningParts.length > 0) {\n    additional_kwargs.reasoning = reasoningParts.join('');\n  }\n\n  if (candidate?.groundingMetadata) {\n    additional_kwargs.groundingMetadata = candidate.groundingMetadata;\n  }\n\n  const isFinalChunk =\n    response.candidates[0]?.finishReason === 'STOP' ||\n    response.candidates[0]?.finishReason === 'MAX_TOKENS' ||\n    response.candidates[0]?.finishReason === 'SAFETY';\n\n  // The GenAI API delivers function calls as complete objects (never partial\n  // arg deltas), so every call on this chunk is sealed on arrival for eager\n  // tool execution.\n  const response_metadata: Record<string, unknown> | undefined =\n    toolCallChunks.length > 0\n      ? {\n        [STREAMED_TOOL_CALL_ADAPTER_METADATA_KEY]:\n            GOOGLE_STREAMED_TOOL_CALL_ADAPTER,\n        [STREAMED_TOOL_CALL_SEAL_METADATA_KEY]: { kind: 'all' },\n      }\n      : undefined;\n\n  return new ChatGenerationChunk({\n    text,\n    message: new AIMessageChunk({\n      content: content,\n      name: !candidateContent ? undefined : candidateContent.role,\n      tool_call_chunks: toolCallChunks,\n      // Each chunk can have unique \"generationInfo\", and merging strategy is unclear,\n      // so leave blank for now.\n      additional_kwargs,\n      response_metadata,\n      usage_metadata: isFinalChunk ? extra.usageMetadata : undefined,\n    }),\n    generationInfo,\n  });\n}\n\n/**\n * Maps a Google GenerateContentResult to a LangChain ChatResult\n */\nexport function mapGenerateContentResultToChatResult(\n  response: EnhancedGenerateContentResponse,\n  extra?: {\n    usageMetadata: UsageMetadata | undefined;\n  }\n): ChatResult {\n  if (!response.candidates || response.candidates.length === 0) {\n    return {\n      generations: [],\n      llmOutput: {\n        filters: response.promptFeedback,\n      },\n    };\n  }\n  const [candidate] = response.candidates as [\n    Partial<GenerateContentCandidate> | undefined,\n  ];\n  const { content: candidateContent, ...generationInfo } = candidate ?? {};\n\n  // Extract function calls directly from parts to preserve thoughtSignature\n  const functionCalls =\n    candidateContent?.parts.reduce(\n      (acc, p) => {\n        if ('functionCall' in p && p.functionCall) {\n          acc.push({\n            ...p,\n            id:\n              'id' in p.functionCall && typeof p.functionCall.id === 'string'\n                ? p.functionCall.id\n                : uuidv4(),\n          });\n        }\n        return acc;\n      },\n      [] as (FunctionCallPart & { id: string; thoughtSignature?: string })[]\n    ) ?? [];\n\n  let content: MessageContent | undefined;\n  const reasoningParts: string[] = [];\n  if (\n    Array.isArray(candidateContent?.parts) &&\n    candidateContent.parts.length === 1 &&\n    (candidateContent.parts[0].text ?? '') !== '' &&\n    !(\n      'thought' in candidateContent.parts[0] &&\n      candidateContent.parts[0].thought === true\n    )\n  ) {\n    content = candidateContent.parts[0].text;\n  } else if (\n    Array.isArray(candidateContent?.parts) &&\n    candidateContent.parts.length > 0\n  ) {\n    content = toLangChainContent(\n      candidateContent.parts\n        .map((p) => {\n          if ('text' in p && 'thought' in p && p.thought === true) {\n            reasoningParts.push(p.text ?? 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'A function available to call.',\n              parameters: jsonSchemaToGeminiParameters(\n                tool.function.parameters\n              ),\n            };\n          }\n          return tool as unknown as GenerativeAIFunctionDeclaration;\n        }\n      ),\n    },\n  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id : undefined;\n}\n\nfunction createGoogleFunctionResponsePart({\n  name,\n  response,\n  id,\n}: {\n  name: string;\n  response: object;\n  id?: string;\n}): Part {\n  const functionId = getGoogleFunctionId(id);\n  const functionResponse: GoogleFunctionResponseWithId = {\n    name,\n    response,\n    ...(functionId != null ? { id: functionId } : {}),\n  };\n  return { functionResponse };\n}\n\n/**\n * Executes a function immediately and returns its result.\n * Functional utility similar to an Immediately Invoked Function Expression (IIFE).\n * @param fn The function to execute.\n * @returns The result of invoking fn.\n */\nexport const iife = <T>(fn: () => T): T => fn();\n\nexport function getMessageAuthor(message: BaseMessage): string {\n  const type = message._getType();\n  if (ChatMessage.isInstance(message)) {\n    return message.role;\n  }\n  if (type === 'tool') {\n    return type;\n  }\n  return message.name ?? type;\n}\n\n/**\n * Maps a message type to a Google Generative AI chat author.\n * @param message The message to map.\n * @param model The model to use for mapping.\n * @returns The message type mapped to a Google Generative AI chat author.\n */\nexport function convertAuthorToRole(\n  author: string\n): (typeof POSSIBLE_ROLES)[number] {\n  switch (author) {\n  /**\n     *  Note: Gemini currently is not supporting system messages\n     *  we will convert them to human messages and merge with following\n     * */\n  case 'supervisor':\n  case 'ai':\n  case 'model': // getMessageAuthor returns message.name. code ex.: return message.name ?? type;\n    return 'model';\n  case 'system':\n    return 'system';\n  case 'human':\n    return 'user';\n  case 'tool':\n  case 'function':\n    return 'function';\n  default:\n    throw new Error(`Unknown / unsupported author: ${author}`);\n  }\n}\n\nfunction messageContentMedia(content: MessageContentComplex): Part {\n  if ('mimeType' in content && 'data' in content) {\n    return {\n      inlineData: {\n        mimeType: content.mimeType,\n        data: content.data,\n      },\n    };\n  }\n  if ('mimeType' in content && 'fileUri' in content) {\n    return {\n      fileData: {\n        mimeType: content.mimeType,\n        fileUri: content.fileUri,\n      },\n    };\n  }\n\n  throw new Error('Invalid media content');\n}\n\nfunction isGoogleServerSideToolPart(\n  content: MessageContentComplex\n): content is MessageContentComplex & GoogleServerSideToolPart {\n  return (\n    'toolCall' in content ||\n    'toolResponse' in content ||\n    content.type === 'toolCall' ||\n    content.type === 'toolResponse'\n  );\n}\n\nfunction convertGoogleServerSideToolPart(\n  content: MessageContentComplex & GoogleServerSideToolPart\n): Part {\n  const metadata: GoogleServerSideToolPartMetadata = {};\n  if ('thought' in content && typeof content.thought === 'boolean') {\n    metadata.thought = content.thought;\n  }\n  if (\n    'thoughtSignature' in content &&\n    typeof content.thoughtSignature === 'string'\n  ) {\n    metadata.thoughtSignature = content.thoughtSignature;\n  }\n  if ('toolCall' in content && content.toolCall != null) {\n    return { toolCall: content.toolCall, ...metadata } as unknown as Part;\n  }\n  if ('toolResponse' in content && content.toolResponse != null) {\n    return {\n      toolResponse: content.toolResponse,\n      ...metadata,\n    } as unknown as Part;\n  }\n\n  return content as Part;\n}\n\nfunction convertGoogleServerSideToolResponsePart(\n  part: Part\n): GoogleServerSideToolPart | undefined {\n  if (\n    'toolCall' in part &&\n    typeof part.toolCall === 'object' &&\n    part.toolCall != null\n  ) {\n    return { ...part, type: 'toolCall', toolCall: part.toolCall };\n  }\n  if (\n    'toolResponse' in part &&\n    typeof part.toolResponse === 'object' &&\n    part.toolResponse != null\n  ) {\n    return { ...part, type: 'toolResponse', toolResponse: part.toolResponse };\n  }\n  return undefined;\n}\n\nfunction inferToolNameFromPreviousMessages(\n  message: ToolMessage | ToolMessageChunk,\n  previousMessages: BaseMessage[]\n): string | undefined {\n  return previousMessages\n    .map((msg) => {\n      if (isAIMessage(msg)) {\n        return msg.tool_calls ?? 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'',\n            data: block.data,\n          },\n        };\n      }\n\n      throw new Error(`Unsupported source type: ${block.source_type}`);\n    },\n\n    fromStandardFileBlock(block): FileDataPart | InlineDataPart | TextPart {\n      if (!isMultimodalModel) {\n        throw new Error('This model does not support files');\n      }\n      if (block.source_type === 'text') {\n        return {\n          text: block.text,\n        };\n      }\n      if (block.source_type === 'url') {\n        const data = parseBase64DataUrl({ dataUrl: block.url });\n        if (data) {\n          return {\n            inlineData: {\n              mimeType: data.mime_type,\n              data: data.data,\n            },\n          };\n        } else {\n          return {\n            fileData: {\n              mimeType: block.mime_type ?? '',\n              fileUri: block.url,\n            },\n          };\n        }\n      }\n\n      if (block.source_type === 'base64') {\n        return {\n          inlineData: {\n            mimeType: block.mime_type ?? '',\n            data: block.data,\n          },\n        };\n      }\n      throw new Error(`Unsupported source type: ${block.source_type}`);\n    },\n  };\n  return standardContentBlockConverter;\n}\n\nfunction _convertLangChainContentToPart(\n  content: MessageContentComplex,\n  isMultimodalModel: boolean\n): Part | undefined {\n  if (isDataContentBlock(content)) {\n    return convertToProviderContentBlock(\n      content,\n      _getStandardContentBlockConverter(isMultimodalModel)\n    );\n  }\n\n  if (isGoogleServerSideToolPart(content)) {\n    return convertGoogleServerSideToolPart(content);\n  }\n\n  if (content.type === 'text') {\n    return { text: content.text };\n  } else if (content.type === 'executableCode') {\n    return { executableCode: content.executableCode };\n  } else if (content.type === 'codeExecutionResult') {\n    return { codeExecutionResult: content.codeExecutionResult };\n  } else if (content.type === 'image_url') {\n    if (!isMultimodalModel) {\n      throw new Error('This model does not support images');\n    }\n    let source: string;\n    if (typeof content.image_url === 'string') {\n      source = content.image_url;\n    } else if (\n      typeof content.image_url === 'object' &&\n      'url' in content.image_url\n    ) {\n      source = content.image_url.url;\n    } else {\n      throw new Error('Please provide image as base64 encoded data URL');\n    }\n    const [dm, data] = source.split(',');\n    if (!dm.startsWith('data:')) {\n      throw new Error('Please provide image as base64 encoded data URL');\n    }\n\n    const [mimeType, encoding] = dm.replace(/^data:/, '').split(';');\n    if (encoding !== 'base64') {\n      throw new Error('Please provide image as base64 encoded data URL');\n    }\n\n    return {\n      inlineData: {\n        data,\n        mimeType,\n      },\n    };\n  } else if (content.type === 'media') {\n    return messageContentMedia(content);\n  } else if (content.type === 'tool_use') {\n    return {\n      functionCall: {\n        name: content.name,\n        args: content.input,\n      },\n    };\n  } else if (\n    content.type?.includes('/') === true &&\n    // Ensure it's a single slash.\n    content.type.split('/').length === 2 &&\n    'data' in content &&\n    typeof content.data === 'string'\n  ) {\n    return {\n      inlineData: {\n        mimeType: content.type,\n        data: content.data,\n      },\n    };\n  } else if ('functionCall' in content) {\n    // No action needed here — function calls will be added later from message.tool_calls\n    return undefined;\n  } else {\n    if ('type' in content) {\n      throw new Error(`Unknown content type ${content.type}`);\n    } else {\n      throw new Error(`Unknown content ${JSON.stringify(content)}`);\n    }\n  }\n}\n\nexport function convertMessageContentToParts(\n  message: BaseMessage,\n  isMultimodalModel: boolean,\n  previousMessages: BaseMessage[],\n  model?: string\n): Part[] {\n  if (isToolMessage(message)) {\n    const messageName =\n      message.name ??\n      inferToolNameFromPreviousMessages(message, previousMessages);\n    if (messageName === undefined) {\n      throw new Error(\n        `Google requires a tool name for each tool call response, and we could not infer a called tool name for ToolMessage \"${message.id}\" from your passed messages. Please populate a \"name\" field on that ToolMessage explicitly.`\n      );\n    }\n\n    const result = Array.isArray(message.content)\n      ? (message.content\n        .map((c) => _convertLangChainContentToPart(c, isMultimodalModel))\n        .filter((p) => p !== undefined) as Part[])\n      : message.content;\n\n    if (message.status === 'error') {\n      return [\n        createGoogleFunctionResponsePart({\n          name: messageName,\n          // The API expects an object with an `error` field if the function call fails.\n          // `error` must be a valid object (not a string or array), so we wrap `message.content` here\n          response: { error: { details: result } },\n          id: message.tool_call_id,\n        }),\n      ];\n    }\n\n    return [\n      createGoogleFunctionResponsePart({\n        name: messageName,\n        // again, can't have a string or array value for `response`, so we wrap it as an object here\n        response: { result },\n        id: message.tool_call_id,\n      }),\n    ];\n  }\n\n  let functionCalls: FunctionCallPart[] = [];\n  const messageParts: Part[] = [];\n\n  if (typeof message.content === 'string' && message.content) {\n    messageParts.push({ text: message.content });\n  }\n\n  if (Array.isArray(message.content)) {\n    messageParts.push(\n      ...(message.content\n        .map((c) => _convertLangChainContentToPart(c, isMultimodalModel))\n        .filter((p) => p !== undefined) as Part[])\n    );\n  }\n\n  const functionThoughtSignatures = (\n    message.additional_kwargs as BaseMessage['additional_kwargs'] | undefined\n  )?.[_FUNCTION_CALL_THOUGHT_SIGNATURES_MAP_KEY] as\n    | Record<string, string>\n    | undefined;\n\n  if (isAIMessage(message) && (message.tool_calls?.length ?? 0) > 0) {\n    functionCalls = (message.tool_calls ?? []).map((tc) => {\n      const thoughtSignature = iife(() => {\n        if (tc.id != null && tc.id !== '') {\n          const signature = functionThoughtSignatures?.[tc.id];\n          if (signature != null && signature !== '') {\n            return signature;\n          }\n        }\n        if (model?.includes('gemini-3') === true) {\n          return DUMMY_SIGNATURE;\n        }\n        return '';\n      });\n      const functionId = getGoogleFunctionId(tc.id);\n      const functionCall: GoogleFunctionCallWithId = {\n        name: tc.name,\n        args: tc.args,\n        ...(functionId != null ? { id: functionId } : {}),\n      };\n\n      return {\n        functionCall,\n        ...(thoughtSignature ? { thoughtSignature } : {}),\n      };\n    });\n  }\n\n  return [...messageParts, ...functionCalls];\n}\n\nexport function convertBaseMessagesToContent(\n  messages: BaseMessage[],\n  isMultimodalModel: boolean,\n  convertSystemMessageToHumanContent: boolean = false,\n\n  model?: string\n): Content[] | undefined {\n  return messages.reduce<{\n    content: Content[] | undefined;\n    mergeWithPreviousContent: boolean;\n  }>(\n    (acc, message, index) => {\n      if (!isBaseMessage(message)) {\n        throw new Error('Unsupported message input');\n      }\n      const author = getMessageAuthor(message);\n      if (author === 'system' && index !== 0) {\n        throw new Error('System message should be the first one');\n      }\n      const role = convertAuthorToRole(author);\n\n      const prevContent = acc.content?.[acc.content.length];\n      if (\n        !acc.mergeWithPreviousContent &&\n        prevContent &&\n        prevContent.role === role\n      ) {\n        throw new Error(\n          'Google Generative AI requires alternate messages between authors'\n        );\n      }\n\n      const parts = convertMessageContentToParts(\n        message,\n        isMultimodalModel,\n        messages.slice(0, index),\n        model\n      );\n\n      if (acc.mergeWithPreviousContent) {\n        const prevContent = acc.content?.[acc.content.length - 1];\n        if (!prevContent) {\n          throw new Error(\n            'There was a problem parsing your system message. Please try a prompt without one.'\n          );\n        }\n        prevContent.parts.push(...parts);\n\n        return {\n          mergeWithPreviousContent: false,\n          content: acc.content,\n        };\n      }\n      let actualRole = role;\n      if (\n        actualRole === 'function' ||\n        (actualRole === 'system' && !convertSystemMessageToHumanContent)\n      ) {\n        // GenerativeAI API will throw an error if the role is not \"user\" or \"model.\"\n        actualRole = 'user';\n      }\n      const content: Content = {\n        role: actualRole,\n        parts,\n      };\n      return {\n        mergeWithPreviousContent:\n          author === 'system' && !convertSystemMessageToHumanContent,\n        content: [...(acc.content ?? []), content],\n      };\n    },\n    { content: [], mergeWithPreviousContent: false }\n  ).content;\n}\n\n/**\n * Gemini models that reject a request whose `contents` end with a `model`-role\n * turn (a \"prefill\"). Google enforces this on newer generations (Gemini 3.6\n * Flash, Gemini 3.5 Flash-Lite) while older/sibling models still accept a\n * trailing model turn, so the rule is model-scoped rather than version-wide.\n * Extend this list as Google applies the restriction to further models.\n * @see https://ai.google.dev/gemini-api/docs/latest-model#api-changes-and-parameter-updates\n */\nconst NO_PREFILL_GEMINI_MODELS = [\n  'gemini-3.6-flash',\n  'gemini-3.5-flash-lite',\n] as const;\n\nexport function rejectsModelTurnPrefill(model?: string): boolean {\n  if (model == null || model === '') {\n    return false;\n  }\n  const modelId = model.toLowerCase().split('/').pop() ?? '';\n  return NO_PREFILL_GEMINI_MODELS.some(\n    (id) => modelId === id || modelId.startsWith(`${id}-`)\n  );\n}\n\n/**\n * Drops trailing `model`-role turns for models that reject prefill (see\n * {@link rejectsModelTurnPrefill}). Such a turn is only produced by prefill\n * flows (e.g. editing an assistant reply and resubmitting); these models return\n * HTTP 400 for it, so we drop it and let the model generate fresh from the\n * preceding user turn. No-op for every other model, preserving working prefill.\n */\nexport function dropUnsupportedModelTurnPrefill(\n  contents: Content[] | undefined,\n  model?: string\n): Content[] | undefined {\n  if (contents == null || contents.length === 0 || !rejectsModelTurnPrefill(model)) {\n    return contents;\n  }\n  let end = contents.length;\n  while (end > 1 && contents[end - 1]?.role === 'model') {\n    end -= 1;\n  }\n  return end === contents.length ? contents : contents.slice(0, end);\n}\n\nexport function convertResponseContentToChatGenerationChunk(\n  response: EnhancedGenerateContentResponse,\n  extra: {\n    usageMetadata?: UsageMetadata | undefined;\n    index: number;\n  }\n): ChatGenerationChunk | null {\n  if (!response.candidates || response.candidates.length === 0) {\n    return null;\n  }\n  const [candidate] = response.candidates as [\n    Partial<GenerateContentCandidate> | undefined,\n  ];\n  const { content: candidateContent, ...generationInfo } = candidate ?? {};\n\n  // Extract function calls directly from parts to preserve thoughtSignature\n  const functionCalls =\n    (candidateContent?.parts as Part[] | undefined)?.reduce(\n      (acc, p) => {\n        if ('functionCall' in p && p.functionCall) {\n          acc.push({\n            ...p,\n            id:\n              'id' in p.functionCall && typeof p.functionCall.id === 'string'\n                ? p.functionCall.id\n                : uuidv4(),\n          });\n        }\n        return acc;\n      },\n      [] as (\n        | undefined\n        | (FunctionCallPart & { id: string; thoughtSignature?: string })\n      )[]\n    ) ?? [];\n\n  let content: MessageContent | undefined;\n  // Checks if some parts do not have text. If false, it means that the content is a string.\n  const reasoningParts: string[] = [];\n  if (\n    candidateContent != null &&\n    Array.isArray(candidateContent.parts) &&\n    candidateContent.parts.every((p) => 'text' in p)\n  ) {\n    // content = candidateContent.parts.map((p) => p.text).join('');\n    const textParts: string[] = [];\n    for (const part of candidateContent.parts) {\n      if ('thought' in part && part.thought === true) {\n        reasoningParts.push(part.text ?? '');\n        continue;\n      }\n      textParts.push(part.text ?? '');\n    }\n    content = textParts.join('');\n  } else if (candidateContent && Array.isArray(candidateContent.parts)) {\n    content = toLangChainContent(\n      candidateContent.parts\n        .map((p) => {\n          if ('text' in p && 'thought' in p && p.thought === true) {\n            reasoningParts.push(p.text ?? '');\n            return undefined;\n          } else if ('text' in p) {\n            return {\n              type: 'text',\n              text: p.text,\n            };\n          } else if ('executableCode' in p) {\n            return {\n              type: 'executableCode',\n              executableCode: p.executableCode,\n            };\n          } else if ('codeExecutionResult' in p) {\n            return {\n              type: 'codeExecutionResult',\n              codeExecutionResult: p.codeExecutionResult,\n            };\n          }\n          const serverSideToolPart = convertGoogleServerSideToolResponsePart(p);\n          if (serverSideToolPart !== undefined) {\n            return serverSideToolPart;\n          }\n          return p;\n        })\n        .filter((p) => p !== undefined)\n    );\n  } else {\n    // no content returned - likely due to abnormal stop reason, e.g. malformed function call\n    content = [];\n  }\n\n  let text = '';\n  if (typeof content === 'string' && content) {\n    text = content;\n  } else if (Array.isArray(content)) {\n    const block = content.find((b) => 'text' in b) as\n      | { text: string }\n      | undefined;\n    text = block?.text ?? '';\n  }\n\n  const toolCallChunks: ToolCallChunk[] = [];\n  if (functionCalls.length > 0) {\n    toolCallChunks.push(\n      ...functionCalls.map((fc) => ({\n        type: 'tool_call_chunk' as const,\n        id: fc?.id,\n        name: fc?.functionCall.name,\n        args: JSON.stringify(fc?.functionCall.args),\n      }))\n    );\n  }\n\n  // Extract thought signatures from function calls for Gemini 3+\n  const functionThoughtSignatures = functionCalls.reduce(\n    (acc, fc) => {\n      if (\n        fc &&\n        'thoughtSignature' in fc &&\n        typeof fc.thoughtSignature === 'string'\n      ) {\n        acc[fc.id] = fc.thoughtSignature;\n      }\n      return acc;\n    },\n    {} as Record<string, string>\n  );\n\n  const additional_kwargs: ChatGeneration['message']['additional_kwargs'] = {\n    [_FUNCTION_CALL_THOUGHT_SIGNATURES_MAP_KEY]: functionThoughtSignatures,\n  };\n\n  if (reasoningParts.length > 0) {\n    additional_kwargs.reasoning = reasoningParts.join('');\n  }\n\n  if (candidate?.groundingMetadata) {\n    additional_kwargs.groundingMetadata = candidate.groundingMetadata;\n  }\n\n  const isFinalChunk =\n    response.candidates[0]?.finishReason === 'STOP' ||\n    response.candidates[0]?.finishReason === 'MAX_TOKENS' ||\n    response.candidates[0]?.finishReason === 'SAFETY';\n\n  // The GenAI API delivers function calls as complete objects (never partial\n  // arg deltas), so every call on this chunk is sealed on arrival for eager\n  // tool execution.\n  const response_metadata: Record<string, unknown> | undefined =\n    toolCallChunks.length > 0\n      ? {\n        [STREAMED_TOOL_CALL_ADAPTER_METADATA_KEY]:\n            GOOGLE_STREAMED_TOOL_CALL_ADAPTER,\n        [STREAMED_TOOL_CALL_SEAL_METADATA_KEY]: { kind: 'all' },\n      }\n      : undefined;\n\n  return new ChatGenerationChunk({\n    text,\n    message: new AIMessageChunk({\n      content: content,\n      name: !candidateContent ? undefined : candidateContent.role,\n      tool_call_chunks: toolCallChunks,\n      // Each chunk can have unique \"generationInfo\", and merging strategy is unclear,\n      // so leave blank for now.\n      additional_kwargs,\n      response_metadata,\n      usage_metadata: isFinalChunk ? extra.usageMetadata : undefined,\n    }),\n    generationInfo,\n  });\n}\n\n/**\n * Maps a Google GenerateContentResult to a LangChain ChatResult\n */\nexport function mapGenerateContentResultToChatResult(\n  response: EnhancedGenerateContentResponse,\n  extra?: {\n    usageMetadata: UsageMetadata | undefined;\n  }\n): ChatResult {\n  if (!response.candidates || response.candidates.length === 0) {\n    return {\n      generations: [],\n      llmOutput: {\n        filters: response.promptFeedback,\n      },\n    };\n  }\n  const [candidate] = response.candidates as [\n    Partial<GenerateContentCandidate> | undefined,\n  ];\n  const { content: candidateContent, ...generationInfo } = candidate ?? {};\n\n  // Extract function calls directly from parts to preserve thoughtSignature\n  const functionCalls =\n    candidateContent?.parts.reduce(\n      (acc, p) => {\n        if ('functionCall' in p && p.functionCall) {\n          acc.push({\n            ...p,\n            id:\n              'id' in p.functionCall && typeof p.functionCall.id === 'string'\n                ? p.functionCall.id\n                : uuidv4(),\n          });\n        }\n        return acc;\n      },\n      [] as (FunctionCallPart & { id: string; thoughtSignature?: string })[]\n    ) ?? [];\n\n  let content: MessageContent | undefined;\n  const reasoningParts: string[] = [];\n  if (\n    Array.isArray(candidateContent?.parts) &&\n    candidateContent.parts.length === 1 &&\n    (candidateContent.parts[0].text ?? '') !== '' &&\n    !(\n      'thought' in candidateContent.parts[0] &&\n      candidateContent.parts[0].thought === true\n    )\n  ) {\n    content = candidateContent.parts[0].text;\n  } else if (\n    Array.isArray(candidateContent?.parts) &&\n    candidateContent.parts.length > 0\n  ) {\n    content = toLangChainContent(\n      candidateContent.parts\n        .map((p) => {\n          if ('text' in p && 'thought' in p && p.thought === true) {\n            reasoningParts.push(p.text ?? '');\n            return undefined;\n          } else if ('text' in p) {\n            return {\n              type: 'text',\n              text: p.text,\n            };\n          } else if ('executableCode' in p) {\n            return {\n              type: 'executableCode',\n              executableCode: p.executableCode,\n            };\n          } else if ('codeExecutionResult' in p) {\n            return {\n              type: 'codeExecutionResult',\n              codeExecutionResult: p.codeExecutionResult,\n            };\n          }\n          const serverSideToolPart = convertGoogleServerSideToolResponsePart(p);\n          if (serverSideToolPart !== undefined) {\n            return serverSideToolPart;\n          }\n          return p;\n        })\n        .filter((p) => p !== undefined)\n    );\n  } else {\n    content = [];\n  }\n  let text = '';\n  if (typeof content === 'string') {\n    text = content;\n  } else if (Array.isArray(content) && content.length > 0) {\n    const block = content.find((b) => 'text' in b) as\n      | { text: string }\n      | undefined;\n    text = block?.text ?? text;\n  }\n\n  const additional_kwargs: ChatGeneration['message']['additional_kwargs'] = {\n    ...generationInfo,\n  };\n  if (reasoningParts.length > 0) {\n    additional_kwargs.reasoning = reasoningParts.join('');\n  }\n\n  // Extract thought signatures from function calls for Gemini 3+\n  const functionThoughtSignatures = functionCalls.reduce(\n    (acc, fc) => {\n      if ('thoughtSignature' in fc && typeof fc.thoughtSignature === 'string') {\n        acc[fc.id] = fc.thoughtSignature;\n      }\n      return acc;\n    },\n    {} as Record<string, string>\n  );\n\n  const tool_calls = functionCalls.map((fc) => ({\n    type: 'tool_call' as const,\n    id: fc.id,\n    name: fc.functionCall.name,\n    args: fc.functionCall.args,\n  }));\n\n  // Store thought signatures map for later retrieval\n  additional_kwargs[_FUNCTION_CALL_THOUGHT_SIGNATURES_MAP_KEY] =\n    functionThoughtSignatures;\n\n  const generation: ChatGeneration = {\n    text,\n    message: new AIMessage({\n      content,\n      tool_calls,\n      additional_kwargs,\n      usage_metadata: extra?.usageMetadata,\n    }),\n    generationInfo,\n  };\n  return {\n    generations: [generation],\n    llmOutput: {\n      tokenUsage: {\n        promptTokens: extra?.usageMetadata?.input_tokens,\n        completionTokens: extra?.usageMetadata?.output_tokens,\n        totalTokens: extra?.usageMetadata?.total_tokens,\n      },\n    },\n  };\n}\n\nexport function convertToGenerativeAITools(\n  tools: GoogleGenerativeAIToolType[]\n): GoogleGenerativeAIFunctionDeclarationsTool[] {\n  if (\n    tools.every(\n      (tool) =>\n        'functionDeclarations' in tool &&\n        Array.isArray(tool.functionDeclarations)\n    )\n  ) {\n    return tools as GoogleGenerativeAIFunctionDeclarationsTool[];\n  }\n  return [\n    {\n      functionDeclarations: tools.map(\n        (tool): GenerativeAIFunctionDeclaration => {\n          if (isLangChainTool(tool)) {\n            const jsonSchema = schemaToGenerativeAIParameters(tool.schema);\n            if (\n              jsonSchema.type === 'object' &&\n              'properties' in jsonSchema &&\n              Object.keys(jsonSchema.properties).length === 0\n            ) {\n              return {\n                name: tool.name,\n                description: tool.description,\n              };\n            }\n            return {\n              name: tool.name,\n              description: tool.description,\n              parameters: jsonSchema,\n            };\n          }\n          if (isOpenAITool(tool)) {\n            return {\n              name: tool.function.name,\n              description:\n                tool.function.description ?? 'A function available to call.',\n              parameters: jsonSchemaToGeminiParameters(\n                tool.function.parameters\n              ),\n            };\n          }\n          return tool as unknown as GenerativeAIFunctionDeclaration;\n        }\n      ),\n    },\n  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package/dist/esm/llm/google/index.mjs

@@ -1,4 +1,4 @@
-import { convertBaseMessagesToContent, convertResponseContentToChatGenerationChunk, mapGenerateContentResultToChatResult } from "./utils/common.mjs";
+import { convertBaseMessagesToContent, convertResponseContentToChatGenerationChunk, dropUnsupportedModelTurnPrefill, mapGenerateContentResultToChatResult } from "./utils/common.mjs";
 import { AIMessageChunk } from "@langchain/core/messages";
 import { ChatGenerationChunk } from "@langchain/core/outputs";
 import { getEnvironmentVariable } from "@langchain/core/utils/env";
@@ -120,6 +120,7 @@ var CustomChatGoogleGenerativeAI = class extends ChatGoogleGenerativeAI {
 			this.client.systemInstruction = systemInstruction;
 			actualPrompt = prompt.slice(1);
 		}
+		actualPrompt = dropUnsupportedModelTurnPrefill(actualPrompt, this.model);
 		const request = {
 			...this.invocationParams(options),
 			contents: actualPrompt
@@ -143,6 +144,7 @@ var CustomChatGoogleGenerativeAI = class extends ChatGoogleGenerativeAI {
 			this.client.systemInstruction = systemInstruction;
 			actualPrompt = prompt.slice(1);
 		}
+		actualPrompt = dropUnsupportedModelTurnPrefill(actualPrompt, this.model);
 		const request = {
 			...this.invocationParams(options),
 			contents: actualPrompt

package/dist/esm/llm/google/index.mjs.map

@@ -1 +1 @@
-{"version":3,"file":"index.mjs","names":["GenerativeAI"],"sources":["../../../../src/llm/google/index.ts"],"sourcesContent":["/* eslint-disable @typescript-eslint/ban-ts-comment */\nimport { AIMessageChunk } from '@langchain/core/messages';\nimport { ChatGenerationChunk } from '@langchain/core/outputs';\nimport { ChatGoogleGenerativeAI } from '@langchain/google-genai';\nimport { getEnvironmentVariable } from '@langchain/core/utils/env';\nimport {\n  FunctionCallingMode,\n  GoogleGenerativeAI as GenerativeAI,\n} from '@google/generative-ai';\nimport type {\n  GenerateContentRequest,\n  SafetySetting,\n  ToolConfig,\n} from '@google/generative-ai';\nimport type { CallbackManagerForLLMRun } from '@langchain/core/callbacks/manager';\nimport type { BaseMessage, UsageMetadata } from '@langchain/core/messages';\nimport type { GeminiApiUsageMetadata, InputTokenDetails } from './types';\nimport type { GoogleClientOptions, GoogleThinkingConfig } from '@/types';\nimport {\n  convertResponseContentToChatGenerationChunk,\n  convertBaseMessagesToContent,\n  mapGenerateContentResultToChatResult,\n} from './utils/common';\n\ntype GoogleToolConfigWithServerSideInvocations = ToolConfig & {\n  includeServerSideToolInvocations?: boolean;\n  functionCallingConfig?: Omit<\n    NonNullable<ToolConfig['functionCallingConfig']>,\n    'mode'\n  > & {\n    mode?:\n      | NonNullable<ToolConfig['functionCallingConfig']>['mode']\n      | 'VALIDATED';\n  };\n};\n\nexport class CustomChatGoogleGenerativeAI extends ChatGoogleGenerativeAI {\n  thinkingConfig?: GoogleThinkingConfig;\n  includeServerSideToolInvocations?: boolean;\n\n  /**\n   * Override to add gemini-3 model support for multimodal and function calling thought signatures\n   */\n  get _isMultimodalModel(): boolean {\n    return (\n      this.model.startsWith('gemini-1.5') ||\n      this.model.startsWith('gemini-2') ||\n      (this.model.startsWith('gemma-3-') &&\n        !this.model.startsWith('gemma-3-1b')) ||\n      this.model.startsWith('gemini-3')\n    );\n  }\n\n  constructor(fields: GoogleClientOptions) {\n    super(fields);\n\n    this.model = fields.model.replace(/^models\\//, '');\n\n    this.maxOutputTokens = fields.maxOutputTokens ?? this.maxOutputTokens;\n\n    if (this.maxOutputTokens != null && this.maxOutputTokens < 0) {\n      throw new Error('`maxOutputTokens` must be a positive integer');\n    }\n\n    this.temperature = fields.temperature ?? this.temperature;\n    if (\n      this.temperature != null &&\n      (this.temperature < 0 || this.temperature > 2)\n    ) {\n      throw new Error('`temperature` must be in the range of [0.0,2.0]');\n    }\n\n    this.topP = fields.topP ?? this.topP;\n    if (this.topP != null && this.topP < 0) {\n      throw new Error('`topP` must be a positive integer');\n    }\n\n    if (this.topP != null && this.topP > 1) {\n      throw new Error('`topP` must be below 1.');\n    }\n\n    this.topK = fields.topK ?? this.topK;\n    if (this.topK != null && this.topK < 0) {\n      throw new Error('`topK` must be a positive integer');\n    }\n\n    this.stopSequences = fields.stopSequences ?? this.stopSequences;\n\n    this.apiKey = fields.apiKey ?? getEnvironmentVariable('GOOGLE_API_KEY');\n    if (this.apiKey == null || this.apiKey === '') {\n      throw new Error(\n        'Please set an API key for Google GenerativeAI ' +\n          'in the environment variable GOOGLE_API_KEY ' +\n          'or in the `apiKey` field of the ' +\n          'ChatGoogleGenerativeAI constructor'\n      );\n    }\n\n    this.safetySettings = fields.safetySettings ?? this.safetySettings;\n    if (this.safetySettings && this.safetySettings.length > 0) {\n      const safetySettingsSet = new Set(\n        this.safetySettings.map((s) => s.category)\n      );\n      if (safetySettingsSet.size !== this.safetySettings.length) {\n        throw new Error(\n          'The categories in `safetySettings` array must be unique'\n        );\n      }\n    }\n\n    this.thinkingConfig = fields.thinkingConfig ?? this.thinkingConfig;\n    this.includeServerSideToolInvocations =\n      fields.includeServerSideToolInvocations ??\n      this.includeServerSideToolInvocations;\n\n    this.streaming = fields.streaming ?? this.streaming;\n    this.json = fields.json;\n\n    // @ts-ignore - Accessing private property from parent class\n    this.client = new GenerativeAI(this.apiKey).getGenerativeModel(\n      {\n        model: this.model,\n        safetySettings: this.safetySettings as SafetySetting[],\n        generationConfig: {\n          stopSequences: this.stopSequences,\n          maxOutputTokens: this.maxOutputTokens,\n          temperature: this.temperature,\n          topP: this.topP,\n          topK: this.topK,\n          ...(this.json != null\n            ? { responseMimeType: 'application/json' }\n            : {}),\n        },\n      },\n      {\n        apiVersion: fields.apiVersion,\n        baseUrl: fields.baseUrl,\n        customHeaders: fields.customHeaders,\n      }\n    );\n    this.streamUsage = fields.streamUsage ?? this.streamUsage;\n  }\n\n  static lc_name(): 'LibreChatGoogleGenerativeAI' {\n    return 'LibreChatGoogleGenerativeAI';\n  }\n\n  /**\n   * Helper function to convert Gemini API usage metadata to LangChain format\n   * Includes support for cached tokens and tier-based tracking for gemini-3-pro-preview\n   */\n  private _convertToUsageMetadata(\n    usageMetadata: GeminiApiUsageMetadata | undefined,\n    model: string\n  ): UsageMetadata | undefined {\n    if (!usageMetadata) {\n      return undefined;\n    }\n\n    const output: UsageMetadata = {\n      input_tokens: usageMetadata.promptTokenCount ?? 0,\n      output_tokens:\n        (usageMetadata.candidatesTokenCount ?? 0) +\n        (usageMetadata.thoughtsTokenCount ?? 0),\n      total_tokens: usageMetadata.totalTokenCount ?? 0,\n    };\n\n    if (usageMetadata.cachedContentTokenCount) {\n      output.input_token_details ??= {};\n      output.input_token_details.cache_read =\n        usageMetadata.cachedContentTokenCount;\n    }\n\n    // gemini-3-pro-preview has bracket based tracking of tokens per request\n    if (model === 'gemini-3-pro-preview') {\n      const over200k = Math.max(\n        0,\n        (usageMetadata.promptTokenCount ?? 0) - 200000\n      );\n      const cachedOver200k = Math.max(\n        0,\n        (usageMetadata.cachedContentTokenCount ?? 0) - 200000\n      );\n      if (over200k) {\n        output.input_token_details = {\n          ...output.input_token_details,\n          over_200k: over200k,\n        } as InputTokenDetails;\n      }\n      if (cachedOver200k) {\n        output.input_token_details = {\n          ...output.input_token_details,\n          cache_read_over_200k: cachedOver200k,\n        } as InputTokenDetails;\n      }\n    }\n\n    return output;\n  }\n\n  invocationParams(\n    options?: this['ParsedCallOptions']\n  ): Omit<GenerateContentRequest, 'contents'> {\n    const params = super.invocationParams(options);\n    if (this.thinkingConfig) {\n      /** @ts-ignore */\n      this.client.generationConfig = {\n        /** @ts-ignore */\n        ...this.client.generationConfig,\n        /** @ts-ignore */\n        thinkingConfig: this.thinkingConfig,\n      };\n    }\n    if (\n      this.includeServerSideToolInvocations === true &&\n      Array.isArray(params.tools) &&\n      params.tools.length > 0\n    ) {\n      const toolConfig = params.toolConfig as\n        | GoogleToolConfigWithServerSideInvocations\n        | undefined;\n      const functionCallingConfig = toolConfig?.functionCallingConfig;\n      params.toolConfig = {\n        ...toolConfig,\n        ...(functionCallingConfig?.mode === FunctionCallingMode.AUTO\n          ? {\n            functionCallingConfig: {\n              ...functionCallingConfig,\n              mode: 'VALIDATED',\n            },\n          }\n          : {}),\n        includeServerSideToolInvocations: true,\n      } as ToolConfig;\n    }\n    return params;\n  }\n\n  async _generate(\n    messages: BaseMessage[],\n    options: this['ParsedCallOptions'],\n    runManager?: CallbackManagerForLLMRun\n  ): Promise<import('@langchain/core/outputs').ChatResult> {\n    const prompt = convertBaseMessagesToContent(\n      messages,\n      this._isMultimodalModel,\n      this.useSystemInstruction,\n      this.model\n    );\n    let actualPrompt = prompt;\n    if (prompt?.[0].role === 'system') {\n      const [systemInstruction] = prompt;\n      /** @ts-ignore */\n      this.client.systemInstruction = systemInstruction;\n      actualPrompt = prompt.slice(1);\n    }\n    const parameters = this.invocationParams(options);\n    const request = {\n      ...parameters,\n      contents: actualPrompt,\n    };\n\n    const res = await this.caller.callWithOptions(\n      { signal: options.signal },\n      async () =>\n        /** @ts-ignore */\n        this.client.generateContent(request)\n    );\n\n    const response = res.response;\n    const usageMetadata = this._convertToUsageMetadata(\n      /** @ts-ignore */\n      response.usageMetadata,\n      this.model\n    );\n\n    /** @ts-ignore */\n    const generationResult = mapGenerateContentResultToChatResult(response, {\n      usageMetadata,\n    });\n\n    await runManager?.handleLLMNewToken(\n      generationResult.generations[0].text || '',\n      undefined,\n      undefined,\n      undefined,\n      undefined,\n      undefined\n    );\n    return generationResult;\n  }\n\n  async *_streamResponseChunks(\n    messages: BaseMessage[],\n    options: this['ParsedCallOptions'],\n    runManager?: CallbackManagerForLLMRun\n  ): AsyncGenerator<ChatGenerationChunk> {\n    const prompt = convertBaseMessagesToContent(\n      messages,\n      this._isMultimodalModel,\n      this.useSystemInstruction,\n      this.model\n    );\n    let actualPrompt = prompt;\n    if (prompt?.[0].role === 'system') {\n      const [systemInstruction] = prompt;\n      /** @ts-ignore */\n      this.client.systemInstruction = systemInstruction;\n      actualPrompt = prompt.slice(1);\n    }\n    const parameters = this.invocationParams(options);\n    const request = {\n      ...parameters,\n      contents: actualPrompt,\n    };\n    const stream = await this.caller.callWithOptions(\n      { signal: options.signal },\n      async () => {\n        /** @ts-ignore */\n        const { stream } = await this.client.generateContentStream(request);\n        return stream;\n      }\n    );\n\n    let index = 0;\n    let lastUsageMetadata: UsageMetadata | undefined;\n    for await (const response of stream) {\n      if (\n        'usageMetadata' in response &&\n        this.streamUsage !== false &&\n        options.streamUsage !== false\n      ) {\n        lastUsageMetadata = this._convertToUsageMetadata(\n          response.usageMetadata as GeminiApiUsageMetadata | undefined,\n          this.model\n        );\n      }\n\n      const chunk = convertResponseContentToChatGenerationChunk(response, {\n        usageMetadata: undefined,\n        index,\n      });\n      index += 1;\n      if (!chunk) {\n        continue;\n      }\n\n      yield chunk;\n      await runManager?.handleLLMNewToken(\n        chunk.text || '',\n        undefined,\n        undefined,\n        undefined,\n        undefined,\n        { chunk }\n      );\n    }\n\n    if (lastUsageMetadata) {\n      const finalChunk = new ChatGenerationChunk({\n        text: '',\n        message: new AIMessageChunk({\n          content: '',\n          usage_metadata: lastUsageMetadata,\n        }),\n      });\n      yield finalChunk;\n      await runManager?.handleLLMNewToken(\n        finalChunk.text || '',\n        undefined,\n        undefined,\n        undefined,\n        undefined,\n        { chunk: finalChunk }\n      );\n    }\n  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+{"version":3,"file":"index.mjs","names":["GenerativeAI"],"sources":["../../../../src/llm/google/index.ts"],"sourcesContent":["/* eslint-disable @typescript-eslint/ban-ts-comment */\nimport { AIMessageChunk } from '@langchain/core/messages';\nimport { ChatGenerationChunk } from '@langchain/core/outputs';\nimport { ChatGoogleGenerativeAI } from '@langchain/google-genai';\nimport { getEnvironmentVariable } from '@langchain/core/utils/env';\nimport {\n  FunctionCallingMode,\n  GoogleGenerativeAI as GenerativeAI,\n} from '@google/generative-ai';\nimport type {\n  GenerateContentRequest,\n  SafetySetting,\n  ToolConfig,\n} from '@google/generative-ai';\nimport type { CallbackManagerForLLMRun } from '@langchain/core/callbacks/manager';\nimport type { BaseMessage, UsageMetadata } from '@langchain/core/messages';\nimport type { GeminiApiUsageMetadata, InputTokenDetails } from './types';\nimport type { GoogleClientOptions, GoogleThinkingConfig } from '@/types';\nimport {\n  convertResponseContentToChatGenerationChunk,\n  convertBaseMessagesToContent,\n  dropUnsupportedModelTurnPrefill,\n  mapGenerateContentResultToChatResult,\n} from './utils/common';\n\ntype GoogleToolConfigWithServerSideInvocations = ToolConfig & {\n  includeServerSideToolInvocations?: boolean;\n  functionCallingConfig?: Omit<\n    NonNullable<ToolConfig['functionCallingConfig']>,\n    'mode'\n  > & {\n    mode?:\n      | NonNullable<ToolConfig['functionCallingConfig']>['mode']\n      | 'VALIDATED';\n  };\n};\n\nexport class CustomChatGoogleGenerativeAI extends ChatGoogleGenerativeAI {\n  thinkingConfig?: GoogleThinkingConfig;\n  includeServerSideToolInvocations?: boolean;\n\n  /**\n   * Override to add gemini-3 model support for multimodal and function calling thought signatures\n   */\n  get _isMultimodalModel(): boolean {\n    return (\n      this.model.startsWith('gemini-1.5') ||\n      this.model.startsWith('gemini-2') ||\n      (this.model.startsWith('gemma-3-') &&\n        !this.model.startsWith('gemma-3-1b')) ||\n      this.model.startsWith('gemini-3')\n    );\n  }\n\n  constructor(fields: GoogleClientOptions) {\n    super(fields);\n\n    this.model = fields.model.replace(/^models\\//, '');\n\n    this.maxOutputTokens = fields.maxOutputTokens ?? this.maxOutputTokens;\n\n    if (this.maxOutputTokens != null && this.maxOutputTokens < 0) {\n      throw new Error('`maxOutputTokens` must be a positive integer');\n    }\n\n    this.temperature = fields.temperature ?? this.temperature;\n    if (\n      this.temperature != null &&\n      (this.temperature < 0 || this.temperature > 2)\n    ) {\n      throw new Error('`temperature` must be in the range of [0.0,2.0]');\n    }\n\n    this.topP = fields.topP ?? this.topP;\n    if (this.topP != null && this.topP < 0) {\n      throw new Error('`topP` must be a positive integer');\n    }\n\n    if (this.topP != null && this.topP > 1) {\n      throw new Error('`topP` must be below 1.');\n    }\n\n    this.topK = fields.topK ?? this.topK;\n    if (this.topK != null && this.topK < 0) {\n      throw new Error('`topK` must be a positive integer');\n    }\n\n    this.stopSequences = fields.stopSequences ?? this.stopSequences;\n\n    this.apiKey = fields.apiKey ?? getEnvironmentVariable('GOOGLE_API_KEY');\n    if (this.apiKey == null || this.apiKey === '') {\n      throw new Error(\n        'Please set an API key for Google GenerativeAI ' +\n          'in the environment variable GOOGLE_API_KEY ' +\n          'or in the `apiKey` field of the ' +\n          'ChatGoogleGenerativeAI constructor'\n      );\n    }\n\n    this.safetySettings = fields.safetySettings ?? this.safetySettings;\n    if (this.safetySettings && this.safetySettings.length > 0) {\n      const safetySettingsSet = new Set(\n        this.safetySettings.map((s) => s.category)\n      );\n      if (safetySettingsSet.size !== this.safetySettings.length) {\n        throw new Error(\n          'The categories in `safetySettings` array must be unique'\n        );\n      }\n    }\n\n    this.thinkingConfig = fields.thinkingConfig ?? this.thinkingConfig;\n    this.includeServerSideToolInvocations =\n      fields.includeServerSideToolInvocations ??\n      this.includeServerSideToolInvocations;\n\n    this.streaming = fields.streaming ?? this.streaming;\n    this.json = fields.json;\n\n    // @ts-ignore - Accessing private property from parent class\n    this.client = new GenerativeAI(this.apiKey).getGenerativeModel(\n      {\n        model: this.model,\n        safetySettings: this.safetySettings as SafetySetting[],\n        generationConfig: {\n          stopSequences: this.stopSequences,\n          maxOutputTokens: this.maxOutputTokens,\n          temperature: this.temperature,\n          topP: this.topP,\n          topK: this.topK,\n          ...(this.json != null\n            ? { responseMimeType: 'application/json' }\n            : {}),\n        },\n      },\n      {\n        apiVersion: fields.apiVersion,\n        baseUrl: fields.baseUrl,\n        customHeaders: fields.customHeaders,\n      }\n    );\n    this.streamUsage = fields.streamUsage ?? this.streamUsage;\n  }\n\n  static lc_name(): 'LibreChatGoogleGenerativeAI' {\n    return 'LibreChatGoogleGenerativeAI';\n  }\n\n  /**\n   * Helper function to convert Gemini API usage metadata to LangChain format\n   * Includes support for cached tokens and tier-based tracking for gemini-3-pro-preview\n   */\n  private _convertToUsageMetadata(\n    usageMetadata: GeminiApiUsageMetadata | undefined,\n    model: string\n  ): UsageMetadata | undefined {\n    if (!usageMetadata) {\n      return undefined;\n    }\n\n    const output: UsageMetadata = {\n      input_tokens: usageMetadata.promptTokenCount ?? 0,\n      output_tokens:\n        (usageMetadata.candidatesTokenCount ?? 0) +\n        (usageMetadata.thoughtsTokenCount ?? 0),\n      total_tokens: usageMetadata.totalTokenCount ?? 0,\n    };\n\n    if (usageMetadata.cachedContentTokenCount) {\n      output.input_token_details ??= {};\n      output.input_token_details.cache_read =\n        usageMetadata.cachedContentTokenCount;\n    }\n\n    // gemini-3-pro-preview has bracket based tracking of tokens per request\n    if (model === 'gemini-3-pro-preview') {\n      const over200k = Math.max(\n        0,\n        (usageMetadata.promptTokenCount ?? 0) - 200000\n      );\n      const cachedOver200k = Math.max(\n        0,\n        (usageMetadata.cachedContentTokenCount ?? 0) - 200000\n      );\n      if (over200k) {\n        output.input_token_details = {\n          ...output.input_token_details,\n          over_200k: over200k,\n        } as InputTokenDetails;\n      }\n      if (cachedOver200k) {\n        output.input_token_details = {\n          ...output.input_token_details,\n          cache_read_over_200k: cachedOver200k,\n        } as InputTokenDetails;\n      }\n    }\n\n    return output;\n  }\n\n  invocationParams(\n    options?: this['ParsedCallOptions']\n  ): Omit<GenerateContentRequest, 'contents'> {\n    const params = super.invocationParams(options);\n    if (this.thinkingConfig) {\n      /** @ts-ignore */\n      this.client.generationConfig = {\n        /** @ts-ignore */\n        ...this.client.generationConfig,\n        /** @ts-ignore */\n        thinkingConfig: this.thinkingConfig,\n      };\n    }\n    if (\n      this.includeServerSideToolInvocations === true &&\n      Array.isArray(params.tools) &&\n      params.tools.length > 0\n    ) {\n      const toolConfig = params.toolConfig as\n        | GoogleToolConfigWithServerSideInvocations\n        | undefined;\n      const functionCallingConfig = toolConfig?.functionCallingConfig;\n      params.toolConfig = {\n        ...toolConfig,\n        ...(functionCallingConfig?.mode === FunctionCallingMode.AUTO\n          ? {\n            functionCallingConfig: {\n              ...functionCallingConfig,\n              mode: 'VALIDATED',\n            },\n          }\n          : {}),\n        includeServerSideToolInvocations: true,\n      } as ToolConfig;\n    }\n    return params;\n  }\n\n  async _generate(\n    messages: BaseMessage[],\n    options: this['ParsedCallOptions'],\n    runManager?: CallbackManagerForLLMRun\n  ): Promise<import('@langchain/core/outputs').ChatResult> {\n    const prompt = convertBaseMessagesToContent(\n      messages,\n      this._isMultimodalModel,\n      this.useSystemInstruction,\n      this.model\n    );\n    let actualPrompt = prompt;\n    if (prompt?.[0].role === 'system') {\n      const [systemInstruction] = prompt;\n      /** @ts-ignore */\n      this.client.systemInstruction = systemInstruction;\n      actualPrompt = prompt.slice(1);\n    }\n    actualPrompt = dropUnsupportedModelTurnPrefill(actualPrompt, this.model);\n    const parameters = this.invocationParams(options);\n    const request = {\n      ...parameters,\n      contents: actualPrompt,\n    };\n\n    const res = await this.caller.callWithOptions(\n      { signal: options.signal },\n      async () =>\n        /** @ts-ignore */\n        this.client.generateContent(request)\n    );\n\n    const response = res.response;\n    const usageMetadata = this._convertToUsageMetadata(\n      /** @ts-ignore */\n      response.usageMetadata,\n      this.model\n    );\n\n    /** @ts-ignore */\n    const generationResult = mapGenerateContentResultToChatResult(response, {\n      usageMetadata,\n    });\n\n    await runManager?.handleLLMNewToken(\n      generationResult.generations[0].text || '',\n      undefined,\n      undefined,\n      undefined,\n      undefined,\n      undefined\n    );\n    return generationResult;\n  }\n\n  async *_streamResponseChunks(\n    messages: BaseMessage[],\n    options: this['ParsedCallOptions'],\n    runManager?: CallbackManagerForLLMRun\n  ): AsyncGenerator<ChatGenerationChunk> {\n    const prompt = convertBaseMessagesToContent(\n      messages,\n      this._isMultimodalModel,\n      this.useSystemInstruction,\n      this.model\n    );\n    let actualPrompt = prompt;\n    if (prompt?.[0].role === 'system') {\n      const [systemInstruction] = prompt;\n      /** @ts-ignore */\n      this.client.systemInstruction = systemInstruction;\n      actualPrompt = prompt.slice(1);\n    }\n    actualPrompt = dropUnsupportedModelTurnPrefill(actualPrompt, this.model);\n    const parameters = this.invocationParams(options);\n    const request = {\n      ...parameters,\n      contents: actualPrompt,\n    };\n    const stream = await this.caller.callWithOptions(\n      { signal: options.signal },\n      async () => {\n        /** @ts-ignore */\n        const { stream } = await this.client.generateContentStream(request);\n        return stream;\n      }\n    );\n\n    let index = 0;\n    let lastUsageMetadata: UsageMetadata | undefined;\n    for await (const response of stream) {\n      if (\n        'usageMetadata' in response &&\n        this.streamUsage !== false &&\n        options.streamUsage !== false\n      ) {\n        lastUsageMetadata = this._convertToUsageMetadata(\n          response.usageMetadata as GeminiApiUsageMetadata | undefined,\n          this.model\n        );\n      }\n\n      const chunk = convertResponseContentToChatGenerationChunk(response, {\n        usageMetadata: undefined,\n        index,\n      });\n      index += 1;\n      if (!chunk) {\n        continue;\n      }\n\n      yield chunk;\n      await runManager?.handleLLMNewToken(\n        chunk.text || '',\n        undefined,\n        undefined,\n        undefined,\n        undefined,\n        { chunk }\n      );\n    }\n\n    if (lastUsageMetadata) {\n      const finalChunk = new ChatGenerationChunk({\n        text: '',\n        message: new AIMessageChunk({\n          content: '',\n          usage_metadata: lastUsageMetadata,\n        }),\n      });\n      yield finalChunk;\n      await runManager?.handleLLMNewToken(\n        finalChunk.text || '',\n        undefined,\n        undefined,\n        undefined,\n        undefined,\n        { chunk: finalChunk }\n      );\n    }\n  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package/dist/esm/llm/google/utils/common.mjs

@@ -277,6 +277,33 @@ function convertBaseMessagesToContent(messages, isMultimodalModel, convertSystem
 		mergeWithPreviousContent: false
 	}).content;
 }
+/**
+* Gemini models that reject a request whose `contents` end with a `model`-role
+* turn (a "prefill"). Google enforces this on newer generations (Gemini 3.6
+* Flash, Gemini 3.5 Flash-Lite) while older/sibling models still accept a
+* trailing model turn, so the rule is model-scoped rather than version-wide.
+* Extend this list as Google applies the restriction to further models.
+* @see https://ai.google.dev/gemini-api/docs/latest-model#api-changes-and-parameter-updates
+*/
+const NO_PREFILL_GEMINI_MODELS = ["gemini-3.6-flash", "gemini-3.5-flash-lite"];
+function rejectsModelTurnPrefill(model) {
+	if (model == null || model === "") return false;
+	const modelId = model.toLowerCase().split("/").pop() ?? "";
+	return NO_PREFILL_GEMINI_MODELS.some((id) => modelId === id || modelId.startsWith(`${id}-`));
+}
+/**
+* Drops trailing `model`-role turns for models that reject prefill (see
+* {@link rejectsModelTurnPrefill}). Such a turn is only produced by prefill
+* flows (e.g. editing an assistant reply and resubmitting); these models return
+* HTTP 400 for it, so we drop it and let the model generate fresh from the
+* preceding user turn. No-op for every other model, preserving working prefill.
+*/
+function dropUnsupportedModelTurnPrefill(contents, model) {
+	if (contents == null || contents.length === 0 || !rejectsModelTurnPrefill(model)) return contents;
+	let end = contents.length;
+	while (end > 1 && contents[end - 1]?.role === "model") end -= 1;
+	return end === contents.length ? contents : contents.slice(0, end);
+}
 function convertResponseContentToChatGenerationChunk(response, extra) {
 	if (!response.candidates || response.candidates.length === 0) return null;
 	const [candidate] = response.candidates;
@@ -432,6 +459,6 @@ function mapGenerateContentResultToChatResult(response, extra) {
 	};
 }
 //#endregion
-export { convertBaseMessagesToContent, convertResponseContentToChatGenerationChunk, mapGenerateContentResultToChatResult };
+export { convertBaseMessagesToContent, convertResponseContentToChatGenerationChunk, dropUnsupportedModelTurnPrefill, mapGenerateContentResultToChatResult };
 
 //# sourceMappingURL=common.mjs.map

package/dist/esm/llm/google/utils/common.mjs.map

@@ -1 +1 @@
-{"version":3,"file":"common.mjs","names":["uuidv4"],"sources":["../../../../../src/llm/google/utils/common.ts"],"sourcesContent":["import { v4 as uuidv4 } from 'uuid';\nimport { ChatGenerationChunk } from '@langchain/core/outputs';\nimport { ToolCallChunk } from '@langchain/core/messages/tool';\nimport { isOpenAITool } from '@langchain/core/language_models/base';\nimport { isLangChainTool } from '@langchain/core/utils/function_calling';\nimport {\n  AIMessage,\n  AIMessageChunk,\n  BaseMessage,\n  ChatMessage,\n  ToolMessage,\n  ToolMessageChunk,\n  MessageContent,\n  MessageContentComplex,\n  UsageMetadata,\n  isAIMessage,\n  isBaseMessage,\n  isToolMessage,\n  StandardContentBlockConverter,\n  parseBase64DataUrl,\n  convertToProviderContentBlock,\n  isDataContentBlock,\n} from '@langchain/core/messages';\nimport {\n  POSSIBLE_ROLES,\n  type Part,\n  type Content,\n  type TextPart,\n  type FileDataPart,\n  type InlineDataPart,\n  type FunctionCallPart,\n  type GenerateContentCandidate,\n  type EnhancedGenerateContentResponse,\n  type FunctionDeclaration as GenerativeAIFunctionDeclaration,\n  type FunctionDeclarationsTool as GoogleGenerativeAIFunctionDeclarationsTool,\n} from '@google/generative-ai';\nimport type { ChatGeneration, ChatResult } from '@langchain/core/outputs';\nimport {\n  STREAMED_TOOL_CALL_SEAL_METADATA_KEY,\n  STREAMED_TOOL_CALL_ADAPTER_METADATA_KEY,\n  GOOGLE_STREAMED_TOOL_CALL_ADAPTER,\n} from '@/tools/streamedToolCallSeals';\nimport {\n  jsonSchemaToGeminiParameters,\n  schemaToGenerativeAIParameters,\n} from './zod_to_genai_parameters';\nimport { toLangChainContent } from '@/messages/langchain';\nimport { GoogleGenerativeAIToolType } from '../types';\n\nexport const _FUNCTION_CALL_THOUGHT_SIGNATURES_MAP_KEY =\n  '__gemini_function_call_thought_signatures__';\n\nconst DUMMY_SIGNATURE =\n  'ErYCCrMCAdHtim9kOoOkrPiCNVsmlpMIKd7ZMxgiFbVQOkgp7nlLcDMzVsZwIzvuT7nQROivoXA72ccC2lSDvR0Gh7dkWaGuj7ctv6t7ZceHnecx0QYa+ix8tYpRfjhyWozQ49lWiws6+YGjCt10KRTyWsZ2h6O7iHTYJwKIRwGUHRKy/qK/6kFxJm5ML00gLq4D8s5Z6DBpp2ZlR+uF4G8jJgeWQgyHWVdx2wGYElaceVAc66tZdPQRdOHpWtgYSI1YdaXgVI8KHY3/EfNc2YqqMIulvkDBAnuMhkAjV9xmBa54Tq+ih3Im4+r3DzqhGqYdsSkhS0kZMwte4Hjs65dZzCw9lANxIqYi1DJ639WNPYihp/DCJCos7o+/EeSPJaio5sgWDyUnMGkY1atsJZ+m7pj7DD5tvQ==';\n\ntype GoogleServerSideToolPart = Part & {\n  type?: 'toolCall' | 'toolResponse';\n  toolCall?: object;\n  toolResponse?: object;\n};\n\ntype GoogleServerSideToolPartMetadata = {\n  thought?: boolean;\n  thoughtSignature?: string;\n};\n\ntype GoogleFunctionCallWithId = FunctionCallPart['functionCall'] & {\n  id?: string;\n};\n\ntype GoogleFunctionResponseWithId = {\n  name: string;\n  response: object;\n  id?: string;\n};\n\nfunction getGoogleFunctionId(id?: string): string | undefined {\n  return id != null && id !== '' ? id : undefined;\n}\n\nfunction createGoogleFunctionResponsePart({\n  name,\n  response,\n  id,\n}: {\n  name: string;\n  response: object;\n  id?: string;\n}): Part {\n  const functionId = getGoogleFunctionId(id);\n  const functionResponse: GoogleFunctionResponseWithId = {\n    name,\n    response,\n    ...(functionId != null ? { id: functionId } : {}),\n  };\n  return { functionResponse };\n}\n\n/**\n * Executes a function immediately and returns its result.\n * Functional utility similar to an Immediately Invoked Function Expression (IIFE).\n * @param fn The function to execute.\n * @returns The result of invoking fn.\n */\nexport const iife = <T>(fn: () => T): T => fn();\n\nexport function getMessageAuthor(message: BaseMessage): string {\n  const type = message._getType();\n  if (ChatMessage.isInstance(message)) {\n    return message.role;\n  }\n  if (type === 'tool') {\n    return type;\n  }\n  return message.name ?? type;\n}\n\n/**\n * Maps a message type to a Google Generative AI chat author.\n * @param message The message to map.\n * @param model The model to use for mapping.\n * @returns The message type mapped to a Google Generative AI chat author.\n */\nexport function convertAuthorToRole(\n  author: string\n): (typeof POSSIBLE_ROLES)[number] {\n  switch (author) {\n  /**\n     *  Note: Gemini currently is not supporting system messages\n     *  we will convert them to human messages and merge with following\n     * */\n  case 'supervisor':\n  case 'ai':\n  case 'model': // getMessageAuthor returns message.name. code ex.: return message.name ?? type;\n    return 'model';\n  case 'system':\n    return 'system';\n  case 'human':\n    return 'user';\n  case 'tool':\n  case 'function':\n    return 'function';\n  default:\n    throw new Error(`Unknown / unsupported author: ${author}`);\n  }\n}\n\nfunction messageContentMedia(content: MessageContentComplex): Part {\n  if ('mimeType' in content && 'data' in content) {\n    return {\n      inlineData: {\n        mimeType: content.mimeType,\n        data: content.data,\n      },\n    };\n  }\n  if ('mimeType' in content && 'fileUri' in content) {\n    return {\n      fileData: {\n        mimeType: content.mimeType,\n        fileUri: content.fileUri,\n      },\n    };\n  }\n\n  throw new Error('Invalid media content');\n}\n\nfunction isGoogleServerSideToolPart(\n  content: MessageContentComplex\n): content is MessageContentComplex & GoogleServerSideToolPart {\n  return (\n    'toolCall' in content ||\n    'toolResponse' in content ||\n    content.type === 'toolCall' ||\n    content.type === 'toolResponse'\n  );\n}\n\nfunction convertGoogleServerSideToolPart(\n  content: MessageContentComplex & GoogleServerSideToolPart\n): Part {\n  const metadata: GoogleServerSideToolPartMetadata = {};\n  if ('thought' in content && typeof content.thought === 'boolean') {\n    metadata.thought = content.thought;\n  }\n  if (\n    'thoughtSignature' in content &&\n    typeof content.thoughtSignature === 'string'\n  ) {\n    metadata.thoughtSignature = content.thoughtSignature;\n  }\n  if ('toolCall' in content && content.toolCall != null) {\n    return { toolCall: content.toolCall, ...metadata } as unknown as Part;\n  }\n  if ('toolResponse' in content && content.toolResponse != null) {\n    return {\n      toolResponse: content.toolResponse,\n      ...metadata,\n    } as unknown as Part;\n  }\n\n  return content as Part;\n}\n\nfunction convertGoogleServerSideToolResponsePart(\n  part: Part\n): GoogleServerSideToolPart | undefined {\n  if (\n    'toolCall' in part &&\n    typeof part.toolCall === 'object' &&\n    part.toolCall != null\n  ) {\n    return { ...part, type: 'toolCall', toolCall: part.toolCall };\n  }\n  if (\n    'toolResponse' in part &&\n    typeof part.toolResponse === 'object' &&\n    part.toolResponse != null\n  ) {\n    return { ...part, type: 'toolResponse', toolResponse: part.toolResponse };\n  }\n  return undefined;\n}\n\nfunction inferToolNameFromPreviousMessages(\n  message: ToolMessage | ToolMessageChunk,\n  previousMessages: BaseMessage[]\n): string | undefined {\n  return previousMessages\n    .map((msg) => {\n      if (isAIMessage(msg)) {\n        return msg.tool_calls ?? [];\n      }\n      return [];\n    })\n    .flat()\n    .find((toolCall) => {\n      return toolCall.id === message.tool_call_id;\n    })?.name;\n}\n\nfunction _getStandardContentBlockConverter(\n  isMultimodalModel: boolean\n): StandardContentBlockConverter<{\n  text: TextPart;\n  image: FileDataPart | InlineDataPart;\n  audio: FileDataPart | InlineDataPart;\n  file: FileDataPart | InlineDataPart | TextPart;\n}> {\n  const standardContentBlockConverter: StandardContentBlockConverter<{\n    text: TextPart;\n    image: FileDataPart | InlineDataPart;\n    audio: FileDataPart | InlineDataPart;\n    file: FileDataPart | InlineDataPart | TextPart;\n  }> = {\n    providerName: 'Google Gemini',\n\n    fromStandardTextBlock(block) {\n      return {\n        text: block.text,\n      };\n    },\n\n    fromStandardImageBlock(block): FileDataPart | InlineDataPart {\n      if (!isMultimodalModel) {\n        throw new Error('This model does not support images');\n      }\n      if (block.source_type === 'url') {\n        const data = parseBase64DataUrl({ dataUrl: block.url });\n        if (data) {\n          return {\n            inlineData: {\n              mimeType: data.mime_type,\n              data: data.data,\n            },\n          };\n        } else {\n          return {\n            fileData: {\n              mimeType: block.mime_type ?? '',\n              fileUri: block.url,\n            },\n          };\n        }\n      }\n\n      if (block.source_type === 'base64') {\n        return {\n          inlineData: {\n            mimeType: block.mime_type ?? '',\n            data: block.data,\n          },\n        };\n      }\n\n      throw new Error(`Unsupported source type: ${block.source_type}`);\n    },\n\n    fromStandardAudioBlock(block): FileDataPart | InlineDataPart {\n      if (!isMultimodalModel) {\n        throw new Error('This model does not support audio');\n      }\n      if (block.source_type === 'url') {\n        const data = parseBase64DataUrl({ dataUrl: block.url });\n        if (data) {\n          return {\n            inlineData: {\n              mimeType: data.mime_type,\n              data: data.data,\n            },\n          };\n        } else {\n          return {\n            fileData: {\n              mimeType: block.mime_type ?? '',\n              fileUri: block.url,\n            },\n          };\n        }\n      }\n\n      if (block.source_type === 'base64') {\n        return {\n          inlineData: {\n            mimeType: block.mime_type ?? '',\n            data: block.data,\n          },\n        };\n      }\n\n      throw new Error(`Unsupported source type: ${block.source_type}`);\n    },\n\n    fromStandardFileBlock(block): FileDataPart | InlineDataPart | TextPart {\n      if (!isMultimodalModel) {\n        throw new Error('This model does not support files');\n      }\n      if (block.source_type === 'text') {\n        return {\n          text: block.text,\n        };\n      }\n      if (block.source_type === 'url') {\n        const data = parseBase64DataUrl({ dataUrl: block.url });\n        if (data) {\n          return {\n            inlineData: {\n              mimeType: data.mime_type,\n              data: data.data,\n            },\n          };\n        } else {\n          return {\n            fileData: {\n              mimeType: block.mime_type ?? '',\n              fileUri: block.url,\n            },\n          };\n        }\n      }\n\n      if (block.source_type === 'base64') {\n        return {\n          inlineData: {\n            mimeType: block.mime_type ?? '',\n            data: block.data,\n          },\n        };\n      }\n      throw new Error(`Unsupported source type: ${block.source_type}`);\n    },\n  };\n  return standardContentBlockConverter;\n}\n\nfunction _convertLangChainContentToPart(\n  content: MessageContentComplex,\n  isMultimodalModel: boolean\n): Part | undefined {\n  if (isDataContentBlock(content)) {\n    return convertToProviderContentBlock(\n      content,\n      _getStandardContentBlockConverter(isMultimodalModel)\n    );\n  }\n\n  if (isGoogleServerSideToolPart(content)) {\n    return convertGoogleServerSideToolPart(content);\n  }\n\n  if (content.type === 'text') {\n    return { text: content.text };\n  } else if (content.type === 'executableCode') {\n    return { executableCode: content.executableCode };\n  } else if (content.type === 'codeExecutionResult') {\n    return { codeExecutionResult: content.codeExecutionResult };\n  } else if (content.type === 'image_url') {\n    if (!isMultimodalModel) {\n      throw new Error('This model does not support images');\n    }\n    let source: string;\n    if (typeof content.image_url === 'string') {\n      source = content.image_url;\n    } else if (\n      typeof content.image_url === 'object' &&\n      'url' in content.image_url\n    ) {\n      source = content.image_url.url;\n    } else {\n      throw new Error('Please provide image as base64 encoded data URL');\n    }\n    const [dm, data] = source.split(',');\n    if (!dm.startsWith('data:')) {\n      throw new Error('Please provide image as base64 encoded data URL');\n    }\n\n    const [mimeType, encoding] = dm.replace(/^data:/, '').split(';');\n    if (encoding !== 'base64') {\n      throw new Error('Please provide image as base64 encoded data URL');\n    }\n\n    return {\n      inlineData: {\n        data,\n        mimeType,\n      },\n    };\n  } else if (content.type === 'media') {\n    return messageContentMedia(content);\n  } else if (content.type === 'tool_use') {\n    return {\n      functionCall: {\n        name: content.name,\n        args: content.input,\n      },\n    };\n  } else if (\n    content.type?.includes('/') === true &&\n    // Ensure it's a single slash.\n    content.type.split('/').length === 2 &&\n    'data' in content &&\n    typeof content.data === 'string'\n  ) {\n    return {\n      inlineData: {\n        mimeType: content.type,\n        data: content.data,\n      },\n    };\n  } else if ('functionCall' in content) {\n    // No action needed here — function calls will be added later from message.tool_calls\n    return undefined;\n  } else {\n    if ('type' in content) {\n      throw new Error(`Unknown content type ${content.type}`);\n    } else {\n      throw new Error(`Unknown content ${JSON.stringify(content)}`);\n    }\n  }\n}\n\nexport function convertMessageContentToParts(\n  message: BaseMessage,\n  isMultimodalModel: boolean,\n  previousMessages: BaseMessage[],\n  model?: string\n): Part[] {\n  if (isToolMessage(message)) {\n    const messageName =\n      message.name ??\n      inferToolNameFromPreviousMessages(message, previousMessages);\n    if (messageName === undefined) {\n      throw new Error(\n        `Google requires a tool name for each tool call response, and we could not infer a called tool name for ToolMessage \"${message.id}\" from your passed messages. Please populate a \"name\" field on that ToolMessage explicitly.`\n      );\n    }\n\n    const result = Array.isArray(message.content)\n      ? (message.content\n        .map((c) => _convertLangChainContentToPart(c, isMultimodalModel))\n        .filter((p) => p !== undefined) as Part[])\n      : message.content;\n\n    if (message.status === 'error') {\n      return [\n        createGoogleFunctionResponsePart({\n          name: messageName,\n          // The API expects an object with an `error` field if the function call fails.\n          // `error` must be a valid object (not a string or array), so we wrap `message.content` here\n          response: { error: { details: result } },\n          id: message.tool_call_id,\n        }),\n      ];\n    }\n\n    return [\n      createGoogleFunctionResponsePart({\n        name: messageName,\n        // again, can't have a string or array value for `response`, so we wrap it as an object here\n        response: { result },\n        id: message.tool_call_id,\n      }),\n    ];\n  }\n\n  let functionCalls: FunctionCallPart[] = [];\n  const messageParts: Part[] = [];\n\n  if (typeof message.content === 'string' && message.content) {\n    messageParts.push({ text: message.content });\n  }\n\n  if (Array.isArray(message.content)) {\n    messageParts.push(\n      ...(message.content\n        .map((c) => _convertLangChainContentToPart(c, isMultimodalModel))\n        .filter((p) => p !== undefined) as Part[])\n    );\n  }\n\n  const functionThoughtSignatures = (\n    message.additional_kwargs as BaseMessage['additional_kwargs'] | undefined\n  )?.[_FUNCTION_CALL_THOUGHT_SIGNATURES_MAP_KEY] as\n    | Record<string, string>\n    | undefined;\n\n  if (isAIMessage(message) && (message.tool_calls?.length ?? 0) > 0) {\n    functionCalls = (message.tool_calls ?? []).map((tc) => {\n      const thoughtSignature = iife(() => {\n        if (tc.id != null && tc.id !== '') {\n          const signature = functionThoughtSignatures?.[tc.id];\n          if (signature != null && signature !== '') {\n            return signature;\n          }\n        }\n        if (model?.includes('gemini-3') === true) {\n          return DUMMY_SIGNATURE;\n        }\n        return '';\n      });\n      const functionId = getGoogleFunctionId(tc.id);\n      const functionCall: GoogleFunctionCallWithId = {\n        name: tc.name,\n        args: tc.args,\n        ...(functionId != null ? { id: functionId } : {}),\n      };\n\n      return {\n        functionCall,\n        ...(thoughtSignature ? { thoughtSignature } : {}),\n      };\n    });\n  }\n\n  return [...messageParts, ...functionCalls];\n}\n\nexport function convertBaseMessagesToContent(\n  messages: BaseMessage[],\n  isMultimodalModel: boolean,\n  convertSystemMessageToHumanContent: boolean = false,\n\n  model?: string\n): Content[] | undefined {\n  return messages.reduce<{\n    content: Content[] | undefined;\n    mergeWithPreviousContent: boolean;\n  }>(\n    (acc, message, index) => {\n      if (!isBaseMessage(message)) {\n        throw new Error('Unsupported message input');\n      }\n      const author = getMessageAuthor(message);\n      if (author === 'system' && index !== 0) {\n        throw new Error('System message should be the first one');\n      }\n      const role = convertAuthorToRole(author);\n\n      const prevContent = acc.content?.[acc.content.length];\n      if (\n        !acc.mergeWithPreviousContent &&\n        prevContent &&\n        prevContent.role === role\n      ) {\n        throw new Error(\n          'Google Generative AI requires alternate messages between authors'\n        );\n      }\n\n      const parts = convertMessageContentToParts(\n        message,\n        isMultimodalModel,\n        messages.slice(0, index),\n        model\n      );\n\n      if (acc.mergeWithPreviousContent) {\n        const prevContent = acc.content?.[acc.content.length - 1];\n        if (!prevContent) {\n          throw new Error(\n            'There was a problem parsing your system message. Please try a prompt without one.'\n          );\n        }\n        prevContent.parts.push(...parts);\n\n        return {\n          mergeWithPreviousContent: false,\n          content: acc.content,\n        };\n      }\n      let actualRole = role;\n      if (\n        actualRole === 'function' ||\n        (actualRole === 'system' && !convertSystemMessageToHumanContent)\n      ) {\n        // GenerativeAI API will throw an error if the role is not \"user\" or \"model.\"\n        actualRole = 'user';\n      }\n      const content: Content = {\n        role: actualRole,\n        parts,\n      };\n      return {\n        mergeWithPreviousContent:\n          author === 'system' && !convertSystemMessageToHumanContent,\n        content: [...(acc.content ?? []), content],\n      };\n    },\n    { content: [], mergeWithPreviousContent: false }\n  ).content;\n}\n\nexport function convertResponseContentToChatGenerationChunk(\n  response: EnhancedGenerateContentResponse,\n  extra: {\n    usageMetadata?: UsageMetadata | undefined;\n    index: number;\n  }\n): ChatGenerationChunk | null {\n  if (!response.candidates || response.candidates.length === 0) {\n    return null;\n  }\n  const [candidate] = response.candidates as [\n    Partial<GenerateContentCandidate> | undefined,\n  ];\n  const { content: candidateContent, ...generationInfo } = candidate ?? {};\n\n  // Extract function calls directly from parts to preserve thoughtSignature\n  const functionCalls =\n    (candidateContent?.parts as Part[] | undefined)?.reduce(\n      (acc, p) => {\n        if ('functionCall' in p && p.functionCall) {\n          acc.push({\n            ...p,\n            id:\n              'id' in p.functionCall && typeof p.functionCall.id === 'string'\n                ? p.functionCall.id\n                : uuidv4(),\n          });\n        }\n        return acc;\n      },\n      [] as (\n        | undefined\n        | (FunctionCallPart & { id: string; thoughtSignature?: string })\n      )[]\n    ) ?? [];\n\n  let content: MessageContent | undefined;\n  // Checks if some parts do not have text. If false, it means that the content is a string.\n  const reasoningParts: string[] = [];\n  if (\n    candidateContent != null &&\n    Array.isArray(candidateContent.parts) &&\n    candidateContent.parts.every((p) => 'text' in p)\n  ) {\n    // content = candidateContent.parts.map((p) => p.text).join('');\n    const textParts: string[] = [];\n    for (const part of candidateContent.parts) {\n      if ('thought' in part && part.thought === true) {\n        reasoningParts.push(part.text ?? '');\n        continue;\n      }\n      textParts.push(part.text ?? '');\n    }\n    content = textParts.join('');\n  } else if (candidateContent && Array.isArray(candidateContent.parts)) {\n    content = toLangChainContent(\n      candidateContent.parts\n        .map((p) => {\n          if ('text' in p && 'thought' in p && p.thought === true) {\n            reasoningParts.push(p.text ?? '');\n            return undefined;\n          } else if ('text' in p) {\n            return {\n              type: 'text',\n              text: p.text,\n            };\n          } else if ('executableCode' in p) {\n            return {\n              type: 'executableCode',\n              executableCode: p.executableCode,\n            };\n          } else if ('codeExecutionResult' in p) {\n            return {\n              type: 'codeExecutionResult',\n              codeExecutionResult: p.codeExecutionResult,\n            };\n          }\n          const serverSideToolPart = convertGoogleServerSideToolResponsePart(p);\n          if (serverSideToolPart !== undefined) {\n            return serverSideToolPart;\n          }\n          return p;\n        })\n        .filter((p) => p !== undefined)\n    );\n  } else {\n    // no content returned - likely due to abnormal stop reason, e.g. malformed function call\n    content = [];\n  }\n\n  let text = '';\n  if (typeof content === 'string' && content) {\n    text = content;\n  } else if (Array.isArray(content)) {\n    const block = content.find((b) => 'text' in b) as\n      | { text: string }\n      | undefined;\n    text = block?.text ?? '';\n  }\n\n  const toolCallChunks: ToolCallChunk[] = [];\n  if (functionCalls.length > 0) {\n    toolCallChunks.push(\n      ...functionCalls.map((fc) => ({\n        type: 'tool_call_chunk' as const,\n        id: fc?.id,\n        name: fc?.functionCall.name,\n        args: JSON.stringify(fc?.functionCall.args),\n      }))\n    );\n  }\n\n  // Extract thought signatures from function calls for Gemini 3+\n  const functionThoughtSignatures = functionCalls.reduce(\n    (acc, fc) => {\n      if (\n        fc &&\n        'thoughtSignature' in fc &&\n        typeof fc.thoughtSignature === 'string'\n      ) {\n        acc[fc.id] = fc.thoughtSignature;\n      }\n      return acc;\n    },\n    {} as Record<string, string>\n  );\n\n  const additional_kwargs: ChatGeneration['message']['additional_kwargs'] = {\n    [_FUNCTION_CALL_THOUGHT_SIGNATURES_MAP_KEY]: functionThoughtSignatures,\n  };\n\n  if (reasoningParts.length > 0) {\n    additional_kwargs.reasoning = reasoningParts.join('');\n  }\n\n  if (candidate?.groundingMetadata) {\n    additional_kwargs.groundingMetadata = candidate.groundingMetadata;\n  }\n\n  const isFinalChunk =\n    response.candidates[0]?.finishReason === 'STOP' ||\n    response.candidates[0]?.finishReason === 'MAX_TOKENS' ||\n    response.candidates[0]?.finishReason === 'SAFETY';\n\n  // The GenAI API delivers function calls as complete objects (never partial\n  // arg deltas), so every call on this chunk is sealed on arrival for eager\n  // tool execution.\n  const response_metadata: Record<string, unknown> | undefined =\n    toolCallChunks.length > 0\n      ? {\n        [STREAMED_TOOL_CALL_ADAPTER_METADATA_KEY]:\n            GOOGLE_STREAMED_TOOL_CALL_ADAPTER,\n        [STREAMED_TOOL_CALL_SEAL_METADATA_KEY]: { kind: 'all' },\n      }\n      : undefined;\n\n  return new ChatGenerationChunk({\n    text,\n    message: new AIMessageChunk({\n      content: content,\n      name: !candidateContent ? undefined : candidateContent.role,\n      tool_call_chunks: toolCallChunks,\n      // Each chunk can have unique \"generationInfo\", and merging strategy is unclear,\n      // so leave blank for now.\n      additional_kwargs,\n      response_metadata,\n      usage_metadata: isFinalChunk ? extra.usageMetadata : undefined,\n    }),\n    generationInfo,\n  });\n}\n\n/**\n * Maps a Google GenerateContentResult to a LangChain ChatResult\n */\nexport function mapGenerateContentResultToChatResult(\n  response: EnhancedGenerateContentResponse,\n  extra?: {\n    usageMetadata: UsageMetadata | undefined;\n  }\n): ChatResult {\n  if (!response.candidates || response.candidates.length === 0) {\n    return {\n      generations: [],\n      llmOutput: {\n        filters: response.promptFeedback,\n      },\n    };\n  }\n  const [candidate] = response.candidates as [\n    Partial<GenerateContentCandidate> | undefined,\n  ];\n  const { content: candidateContent, ...generationInfo } = candidate ?? {};\n\n  // Extract function calls directly from parts to preserve thoughtSignature\n  const functionCalls =\n    candidateContent?.parts.reduce(\n      (acc, p) => {\n        if ('functionCall' in p && p.functionCall) {\n          acc.push({\n            ...p,\n            id:\n              'id' in p.functionCall && typeof p.functionCall.id === 'string'\n                ? p.functionCall.id\n                : uuidv4(),\n          });\n        }\n        return acc;\n      },\n      [] as (FunctionCallPart & { id: string; thoughtSignature?: string })[]\n    ) ?? [];\n\n  let content: MessageContent | undefined;\n  const reasoningParts: string[] = [];\n  if (\n    Array.isArray(candidateContent?.parts) &&\n    candidateContent.parts.length === 1 &&\n    (candidateContent.parts[0].text ?? '') !== '' &&\n    !(\n      'thought' in candidateContent.parts[0] &&\n      candidateContent.parts[0].thought === true\n    )\n  ) {\n    content = candidateContent.parts[0].text;\n  } else if (\n    Array.isArray(candidateContent?.parts) &&\n    candidateContent.parts.length > 0\n  ) {\n    content = toLangChainContent(\n      candidateContent.parts\n        .map((p) => {\n          if ('text' in p && 'thought' in p && p.thought === true) {\n            reasoningParts.push(p.text ?? 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'A function available to call.',\n              parameters: jsonSchemaToGeminiParameters(\n                tool.function.parameters\n              ),\n            };\n          }\n          return tool as unknown as GenerativeAIFunctionDeclaration;\n        }\n      ),\n    },\n  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+{"version":3,"file":"common.mjs","names":["uuidv4"],"sources":["../../../../../src/llm/google/utils/common.ts"],"sourcesContent":["import { v4 as uuidv4 } from 'uuid';\nimport { ChatGenerationChunk } from '@langchain/core/outputs';\nimport { ToolCallChunk } from '@langchain/core/messages/tool';\nimport { isOpenAITool } from '@langchain/core/language_models/base';\nimport { isLangChainTool } from '@langchain/core/utils/function_calling';\nimport {\n  AIMessage,\n  AIMessageChunk,\n  BaseMessage,\n  ChatMessage,\n  ToolMessage,\n  ToolMessageChunk,\n  MessageContent,\n  MessageContentComplex,\n  UsageMetadata,\n  isAIMessage,\n  isBaseMessage,\n  isToolMessage,\n  StandardContentBlockConverter,\n  parseBase64DataUrl,\n  convertToProviderContentBlock,\n  isDataContentBlock,\n} from '@langchain/core/messages';\nimport {\n  POSSIBLE_ROLES,\n  type Part,\n  type Content,\n  type TextPart,\n  type FileDataPart,\n  type InlineDataPart,\n  type FunctionCallPart,\n  type GenerateContentCandidate,\n  type EnhancedGenerateContentResponse,\n  type FunctionDeclaration as GenerativeAIFunctionDeclaration,\n  type FunctionDeclarationsTool as GoogleGenerativeAIFunctionDeclarationsTool,\n} from '@google/generative-ai';\nimport type { ChatGeneration, ChatResult } from '@langchain/core/outputs';\nimport {\n  STREAMED_TOOL_CALL_SEAL_METADATA_KEY,\n  STREAMED_TOOL_CALL_ADAPTER_METADATA_KEY,\n  GOOGLE_STREAMED_TOOL_CALL_ADAPTER,\n} from '@/tools/streamedToolCallSeals';\nimport {\n  jsonSchemaToGeminiParameters,\n  schemaToGenerativeAIParameters,\n} from './zod_to_genai_parameters';\nimport { toLangChainContent } from '@/messages/langchain';\nimport { GoogleGenerativeAIToolType } from '../types';\n\nexport const _FUNCTION_CALL_THOUGHT_SIGNATURES_MAP_KEY =\n  '__gemini_function_call_thought_signatures__';\n\nconst DUMMY_SIGNATURE =\n  'ErYCCrMCAdHtim9kOoOkrPiCNVsmlpMIKd7ZMxgiFbVQOkgp7nlLcDMzVsZwIzvuT7nQROivoXA72ccC2lSDvR0Gh7dkWaGuj7ctv6t7ZceHnecx0QYa+ix8tYpRfjhyWozQ49lWiws6+YGjCt10KRTyWsZ2h6O7iHTYJwKIRwGUHRKy/qK/6kFxJm5ML00gLq4D8s5Z6DBpp2ZlR+uF4G8jJgeWQgyHWVdx2wGYElaceVAc66tZdPQRdOHpWtgYSI1YdaXgVI8KHY3/EfNc2YqqMIulvkDBAnuMhkAjV9xmBa54Tq+ih3Im4+r3DzqhGqYdsSkhS0kZMwte4Hjs65dZzCw9lANxIqYi1DJ639WNPYihp/DCJCos7o+/EeSPJaio5sgWDyUnMGkY1atsJZ+m7pj7DD5tvQ==';\n\ntype GoogleServerSideToolPart = Part & {\n  type?: 'toolCall' | 'toolResponse';\n  toolCall?: object;\n  toolResponse?: object;\n};\n\ntype GoogleServerSideToolPartMetadata = {\n  thought?: boolean;\n  thoughtSignature?: string;\n};\n\ntype GoogleFunctionCallWithId = FunctionCallPart['functionCall'] & {\n  id?: string;\n};\n\ntype GoogleFunctionResponseWithId = {\n  name: string;\n  response: object;\n  id?: string;\n};\n\nfunction getGoogleFunctionId(id?: string): string | undefined {\n  return id != null && id !== '' ? id : undefined;\n}\n\nfunction createGoogleFunctionResponsePart({\n  name,\n  response,\n  id,\n}: {\n  name: string;\n  response: object;\n  id?: string;\n}): Part {\n  const functionId = getGoogleFunctionId(id);\n  const functionResponse: GoogleFunctionResponseWithId = {\n    name,\n    response,\n    ...(functionId != null ? { id: functionId } : {}),\n  };\n  return { functionResponse };\n}\n\n/**\n * Executes a function immediately and returns its result.\n * Functional utility similar to an Immediately Invoked Function Expression (IIFE).\n * @param fn The function to execute.\n * @returns The result of invoking fn.\n */\nexport const iife = <T>(fn: () => T): T => fn();\n\nexport function getMessageAuthor(message: BaseMessage): string {\n  const type = message._getType();\n  if (ChatMessage.isInstance(message)) {\n    return message.role;\n  }\n  if (type === 'tool') {\n    return type;\n  }\n  return message.name ?? type;\n}\n\n/**\n * Maps a message type to a Google Generative AI chat author.\n * @param message The message to map.\n * @param model The model to use for mapping.\n * @returns The message type mapped to a Google Generative AI chat author.\n */\nexport function convertAuthorToRole(\n  author: string\n): (typeof POSSIBLE_ROLES)[number] {\n  switch (author) {\n  /**\n     *  Note: Gemini currently is not supporting system messages\n     *  we will convert them to human messages and merge with following\n     * */\n  case 'supervisor':\n  case 'ai':\n  case 'model': // getMessageAuthor returns message.name. code ex.: return message.name ?? type;\n    return 'model';\n  case 'system':\n    return 'system';\n  case 'human':\n    return 'user';\n  case 'tool':\n  case 'function':\n    return 'function';\n  default:\n    throw new Error(`Unknown / unsupported author: ${author}`);\n  }\n}\n\nfunction messageContentMedia(content: MessageContentComplex): Part {\n  if ('mimeType' in content && 'data' in content) {\n    return {\n      inlineData: {\n        mimeType: content.mimeType,\n        data: content.data,\n      },\n    };\n  }\n  if ('mimeType' in content && 'fileUri' in content) {\n    return {\n      fileData: {\n        mimeType: content.mimeType,\n        fileUri: content.fileUri,\n      },\n    };\n  }\n\n  throw new Error('Invalid media content');\n}\n\nfunction isGoogleServerSideToolPart(\n  content: MessageContentComplex\n): content is MessageContentComplex & GoogleServerSideToolPart {\n  return (\n    'toolCall' in content ||\n    'toolResponse' in content ||\n    content.type === 'toolCall' ||\n    content.type === 'toolResponse'\n  );\n}\n\nfunction convertGoogleServerSideToolPart(\n  content: MessageContentComplex & GoogleServerSideToolPart\n): Part {\n  const metadata: GoogleServerSideToolPartMetadata = {};\n  if ('thought' in content && typeof content.thought === 'boolean') {\n    metadata.thought = content.thought;\n  }\n  if (\n    'thoughtSignature' in content &&\n    typeof content.thoughtSignature === 'string'\n  ) {\n    metadata.thoughtSignature = content.thoughtSignature;\n  }\n  if ('toolCall' in content && content.toolCall != null) {\n    return { toolCall: content.toolCall, ...metadata } as unknown as Part;\n  }\n  if ('toolResponse' in content && content.toolResponse != null) {\n    return {\n      toolResponse: content.toolResponse,\n      ...metadata,\n    } as unknown as Part;\n  }\n\n  return content as Part;\n}\n\nfunction convertGoogleServerSideToolResponsePart(\n  part: Part\n): GoogleServerSideToolPart | undefined {\n  if (\n    'toolCall' in part &&\n    typeof part.toolCall === 'object' &&\n    part.toolCall != null\n  ) {\n    return { ...part, type: 'toolCall', toolCall: part.toolCall };\n  }\n  if (\n    'toolResponse' in part &&\n    typeof part.toolResponse === 'object' &&\n    part.toolResponse != null\n  ) {\n    return { ...part, type: 'toolResponse', toolResponse: part.toolResponse };\n  }\n  return undefined;\n}\n\nfunction inferToolNameFromPreviousMessages(\n  message: ToolMessage | ToolMessageChunk,\n  previousMessages: BaseMessage[]\n): string | undefined {\n  return previousMessages\n    .map((msg) => {\n      if (isAIMessage(msg)) {\n        return msg.tool_calls ?? 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'',\n            data: block.data,\n          },\n        };\n      }\n\n      throw new Error(`Unsupported source type: ${block.source_type}`);\n    },\n\n    fromStandardFileBlock(block): FileDataPart | InlineDataPart | TextPart {\n      if (!isMultimodalModel) {\n        throw new Error('This model does not support files');\n      }\n      if (block.source_type === 'text') {\n        return {\n          text: block.text,\n        };\n      }\n      if (block.source_type === 'url') {\n        const data = parseBase64DataUrl({ dataUrl: block.url });\n        if (data) {\n          return {\n            inlineData: {\n              mimeType: data.mime_type,\n              data: data.data,\n            },\n          };\n        } else {\n          return {\n            fileData: {\n              mimeType: block.mime_type ?? '',\n              fileUri: block.url,\n            },\n          };\n        }\n      }\n\n      if (block.source_type === 'base64') {\n        return {\n          inlineData: {\n            mimeType: block.mime_type ?? '',\n            data: block.data,\n          },\n        };\n      }\n      throw new Error(`Unsupported source type: ${block.source_type}`);\n    },\n  };\n  return standardContentBlockConverter;\n}\n\nfunction _convertLangChainContentToPart(\n  content: MessageContentComplex,\n  isMultimodalModel: boolean\n): Part | undefined {\n  if (isDataContentBlock(content)) {\n    return convertToProviderContentBlock(\n      content,\n      _getStandardContentBlockConverter(isMultimodalModel)\n    );\n  }\n\n  if (isGoogleServerSideToolPart(content)) {\n    return convertGoogleServerSideToolPart(content);\n  }\n\n  if (content.type === 'text') {\n    return { text: content.text };\n  } else if (content.type === 'executableCode') {\n    return { executableCode: content.executableCode };\n  } else if (content.type === 'codeExecutionResult') {\n    return { codeExecutionResult: content.codeExecutionResult };\n  } else if (content.type === 'image_url') {\n    if (!isMultimodalModel) {\n      throw new Error('This model does not support images');\n    }\n    let source: string;\n    if (typeof content.image_url === 'string') {\n      source = content.image_url;\n    } else if (\n      typeof content.image_url === 'object' &&\n      'url' in content.image_url\n    ) {\n      source = content.image_url.url;\n    } else {\n      throw new Error('Please provide image as base64 encoded data URL');\n    }\n    const [dm, data] = source.split(',');\n    if (!dm.startsWith('data:')) {\n      throw new Error('Please provide image as base64 encoded data URL');\n    }\n\n    const [mimeType, encoding] = dm.replace(/^data:/, '').split(';');\n    if (encoding !== 'base64') {\n      throw new Error('Please provide image as base64 encoded data URL');\n    }\n\n    return {\n      inlineData: {\n        data,\n        mimeType,\n      },\n    };\n  } else if (content.type === 'media') {\n    return messageContentMedia(content);\n  } else if (content.type === 'tool_use') {\n    return {\n      functionCall: {\n        name: content.name,\n        args: content.input,\n      },\n    };\n  } else if (\n    content.type?.includes('/') === true &&\n    // Ensure it's a single slash.\n    content.type.split('/').length === 2 &&\n    'data' in content &&\n    typeof content.data === 'string'\n  ) {\n    return {\n      inlineData: {\n        mimeType: content.type,\n        data: content.data,\n      },\n    };\n  } else if ('functionCall' in content) {\n    // No action needed here — function calls will be added later from message.tool_calls\n    return undefined;\n  } else {\n    if ('type' in content) {\n      throw new Error(`Unknown content type ${content.type}`);\n    } else {\n      throw new Error(`Unknown content ${JSON.stringify(content)}`);\n    }\n  }\n}\n\nexport function convertMessageContentToParts(\n  message: BaseMessage,\n  isMultimodalModel: boolean,\n  previousMessages: BaseMessage[],\n  model?: string\n): Part[] {\n  if (isToolMessage(message)) {\n    const messageName =\n      message.name ??\n      inferToolNameFromPreviousMessages(message, previousMessages);\n    if (messageName === undefined) {\n      throw new Error(\n        `Google requires a tool name for each tool call response, and we could not infer a called tool name for ToolMessage \"${message.id}\" from your passed messages. Please populate a \"name\" field on that ToolMessage explicitly.`\n      );\n    }\n\n    const result = Array.isArray(message.content)\n      ? (message.content\n        .map((c) => _convertLangChainContentToPart(c, isMultimodalModel))\n        .filter((p) => p !== undefined) as Part[])\n      : message.content;\n\n    if (message.status === 'error') {\n      return [\n        createGoogleFunctionResponsePart({\n          name: messageName,\n          // The API expects an object with an `error` field if the function call fails.\n          // `error` must be a valid object (not a string or array), so we wrap `message.content` here\n          response: { error: { details: result } },\n          id: message.tool_call_id,\n        }),\n      ];\n    }\n\n    return [\n      createGoogleFunctionResponsePart({\n        name: messageName,\n        // again, can't have a string or array value for `response`, so we wrap it as an object here\n        response: { result },\n        id: message.tool_call_id,\n      }),\n    ];\n  }\n\n  let functionCalls: FunctionCallPart[] = [];\n  const messageParts: Part[] = [];\n\n  if (typeof message.content === 'string' && message.content) {\n    messageParts.push({ text: message.content });\n  }\n\n  if (Array.isArray(message.content)) {\n    messageParts.push(\n      ...(message.content\n        .map((c) => _convertLangChainContentToPart(c, isMultimodalModel))\n        .filter((p) => p !== undefined) as Part[])\n    );\n  }\n\n  const functionThoughtSignatures = (\n    message.additional_kwargs as BaseMessage['additional_kwargs'] | undefined\n  )?.[_FUNCTION_CALL_THOUGHT_SIGNATURES_MAP_KEY] as\n    | Record<string, string>\n    | undefined;\n\n  if (isAIMessage(message) && (message.tool_calls?.length ?? 0) > 0) {\n    functionCalls = (message.tool_calls ?? []).map((tc) => {\n      const thoughtSignature = iife(() => {\n        if (tc.id != null && tc.id !== '') {\n          const signature = functionThoughtSignatures?.[tc.id];\n          if (signature != null && signature !== '') {\n            return signature;\n          }\n        }\n        if (model?.includes('gemini-3') === true) {\n          return DUMMY_SIGNATURE;\n        }\n        return '';\n      });\n      const functionId = getGoogleFunctionId(tc.id);\n      const functionCall: GoogleFunctionCallWithId = {\n        name: tc.name,\n        args: tc.args,\n        ...(functionId != null ? { id: functionId } : {}),\n      };\n\n      return {\n        functionCall,\n        ...(thoughtSignature ? { thoughtSignature } : {}),\n      };\n    });\n  }\n\n  return [...messageParts, ...functionCalls];\n}\n\nexport function convertBaseMessagesToContent(\n  messages: BaseMessage[],\n  isMultimodalModel: boolean,\n  convertSystemMessageToHumanContent: boolean = false,\n\n  model?: string\n): Content[] | undefined {\n  return messages.reduce<{\n    content: Content[] | undefined;\n    mergeWithPreviousContent: boolean;\n  }>(\n    (acc, message, index) => {\n      if (!isBaseMessage(message)) {\n        throw new Error('Unsupported message input');\n      }\n      const author = getMessageAuthor(message);\n      if (author === 'system' && index !== 0) {\n        throw new Error('System message should be the first one');\n      }\n      const role = convertAuthorToRole(author);\n\n      const prevContent = acc.content?.[acc.content.length];\n      if (\n        !acc.mergeWithPreviousContent &&\n        prevContent &&\n        prevContent.role === role\n      ) {\n        throw new Error(\n          'Google Generative AI requires alternate messages between authors'\n        );\n      }\n\n      const parts = convertMessageContentToParts(\n        message,\n        isMultimodalModel,\n        messages.slice(0, index),\n        model\n      );\n\n      if (acc.mergeWithPreviousContent) {\n        const prevContent = acc.content?.[acc.content.length - 1];\n        if (!prevContent) {\n          throw new Error(\n            'There was a problem parsing your system message. Please try a prompt without one.'\n          );\n        }\n        prevContent.parts.push(...parts);\n\n        return {\n          mergeWithPreviousContent: false,\n          content: acc.content,\n        };\n      }\n      let actualRole = role;\n      if (\n        actualRole === 'function' ||\n        (actualRole === 'system' && !convertSystemMessageToHumanContent)\n      ) {\n        // GenerativeAI API will throw an error if the role is not \"user\" or \"model.\"\n        actualRole = 'user';\n      }\n      const content: Content = {\n        role: actualRole,\n        parts,\n      };\n      return {\n        mergeWithPreviousContent:\n          author === 'system' && !convertSystemMessageToHumanContent,\n        content: [...(acc.content ?? []), content],\n      };\n    },\n    { content: [], mergeWithPreviousContent: false }\n  ).content;\n}\n\n/**\n * Gemini models that reject a request whose `contents` end with a `model`-role\n * turn (a \"prefill\"). Google enforces this on newer generations (Gemini 3.6\n * Flash, Gemini 3.5 Flash-Lite) while older/sibling models still accept a\n * trailing model turn, so the rule is model-scoped rather than version-wide.\n * Extend this list as Google applies the restriction to further models.\n * @see https://ai.google.dev/gemini-api/docs/latest-model#api-changes-and-parameter-updates\n */\nconst NO_PREFILL_GEMINI_MODELS = [\n  'gemini-3.6-flash',\n  'gemini-3.5-flash-lite',\n] as const;\n\nexport function rejectsModelTurnPrefill(model?: string): boolean {\n  if (model == null || model === '') {\n    return false;\n  }\n  const modelId = model.toLowerCase().split('/').pop() ?? '';\n  return NO_PREFILL_GEMINI_MODELS.some(\n    (id) => modelId === id || modelId.startsWith(`${id}-`)\n  );\n}\n\n/**\n * Drops trailing `model`-role turns for models that reject prefill (see\n * {@link rejectsModelTurnPrefill}). Such a turn is only produced by prefill\n * flows (e.g. editing an assistant reply and resubmitting); these models return\n * HTTP 400 for it, so we drop it and let the model generate fresh from the\n * preceding user turn. No-op for every other model, preserving working prefill.\n */\nexport function dropUnsupportedModelTurnPrefill(\n  contents: Content[] | undefined,\n  model?: string\n): Content[] | undefined {\n  if (contents == null || contents.length === 0 || !rejectsModelTurnPrefill(model)) {\n    return contents;\n  }\n  let end = contents.length;\n  while (end > 1 && contents[end - 1]?.role === 'model') {\n    end -= 1;\n  }\n  return end === contents.length ? contents : contents.slice(0, end);\n}\n\nexport function convertResponseContentToChatGenerationChunk(\n  response: EnhancedGenerateContentResponse,\n  extra: {\n    usageMetadata?: UsageMetadata | undefined;\n    index: number;\n  }\n): ChatGenerationChunk | null {\n  if (!response.candidates || response.candidates.length === 0) {\n    return null;\n  }\n  const [candidate] = response.candidates as [\n    Partial<GenerateContentCandidate> | undefined,\n  ];\n  const { content: candidateContent, ...generationInfo } = candidate ?? {};\n\n  // Extract function calls directly from parts to preserve thoughtSignature\n  const functionCalls =\n    (candidateContent?.parts as Part[] | undefined)?.reduce(\n      (acc, p) => {\n        if ('functionCall' in p && p.functionCall) {\n          acc.push({\n            ...p,\n            id:\n              'id' in p.functionCall && typeof p.functionCall.id === 'string'\n                ? p.functionCall.id\n                : uuidv4(),\n          });\n        }\n        return acc;\n      },\n      [] as (\n        | undefined\n        | (FunctionCallPart & { id: string; thoughtSignature?: string })\n      )[]\n    ) ?? [];\n\n  let content: MessageContent | undefined;\n  // Checks if some parts do not have text. If false, it means that the content is a string.\n  const reasoningParts: string[] = [];\n  if (\n    candidateContent != null &&\n    Array.isArray(candidateContent.parts) &&\n    candidateContent.parts.every((p) => 'text' in p)\n  ) {\n    // content = candidateContent.parts.map((p) => p.text).join('');\n    const textParts: string[] = [];\n    for (const part of candidateContent.parts) {\n      if ('thought' in part && part.thought === true) {\n        reasoningParts.push(part.text ?? '');\n        continue;\n      }\n      textParts.push(part.text ?? '');\n    }\n    content = textParts.join('');\n  } else if (candidateContent && Array.isArray(candidateContent.parts)) {\n    content = toLangChainContent(\n      candidateContent.parts\n        .map((p) => {\n          if ('text' in p && 'thought' in p && p.thought === true) {\n            reasoningParts.push(p.text ?? '');\n            return undefined;\n          } else if ('text' in p) {\n            return {\n              type: 'text',\n              text: p.text,\n            };\n          } else if ('executableCode' in p) {\n            return {\n              type: 'executableCode',\n              executableCode: p.executableCode,\n            };\n          } else if ('codeExecutionResult' in p) {\n            return {\n              type: 'codeExecutionResult',\n              codeExecutionResult: p.codeExecutionResult,\n            };\n          }\n          const serverSideToolPart = convertGoogleServerSideToolResponsePart(p);\n          if (serverSideToolPart !== undefined) {\n            return serverSideToolPart;\n          }\n          return p;\n        })\n        .filter((p) => p !== undefined)\n    );\n  } else {\n    // no content returned - likely due to abnormal stop reason, e.g. malformed function call\n    content = [];\n  }\n\n  let text = '';\n  if (typeof content === 'string' && content) {\n    text = content;\n  } else if (Array.isArray(content)) {\n    const block = content.find((b) => 'text' in b) as\n      | { text: string }\n      | undefined;\n    text = block?.text ?? '';\n  }\n\n  const toolCallChunks: ToolCallChunk[] = [];\n  if (functionCalls.length > 0) {\n    toolCallChunks.push(\n      ...functionCalls.map((fc) => ({\n        type: 'tool_call_chunk' as const,\n        id: fc?.id,\n        name: fc?.functionCall.name,\n        args: JSON.stringify(fc?.functionCall.args),\n      }))\n    );\n  }\n\n  // Extract thought signatures from function calls for Gemini 3+\n  const functionThoughtSignatures = functionCalls.reduce(\n    (acc, fc) => {\n      if (\n        fc &&\n        'thoughtSignature' in fc &&\n        typeof fc.thoughtSignature === 'string'\n      ) {\n        acc[fc.id] = fc.thoughtSignature;\n      }\n      return acc;\n    },\n    {} as Record<string, string>\n  );\n\n  const additional_kwargs: ChatGeneration['message']['additional_kwargs'] = {\n    [_FUNCTION_CALL_THOUGHT_SIGNATURES_MAP_KEY]: functionThoughtSignatures,\n  };\n\n  if (reasoningParts.length > 0) {\n    additional_kwargs.reasoning = reasoningParts.join('');\n  }\n\n  if (candidate?.groundingMetadata) {\n    additional_kwargs.groundingMetadata = candidate.groundingMetadata;\n  }\n\n  const isFinalChunk =\n    response.candidates[0]?.finishReason === 'STOP' ||\n    response.candidates[0]?.finishReason === 'MAX_TOKENS' ||\n    response.candidates[0]?.finishReason === 'SAFETY';\n\n  // The GenAI API delivers function calls as complete objects (never partial\n  // arg deltas), so every call on this chunk is sealed on arrival for eager\n  // tool execution.\n  const response_metadata: Record<string, unknown> | undefined =\n    toolCallChunks.length > 0\n      ? {\n        [STREAMED_TOOL_CALL_ADAPTER_METADATA_KEY]:\n            GOOGLE_STREAMED_TOOL_CALL_ADAPTER,\n        [STREAMED_TOOL_CALL_SEAL_METADATA_KEY]: { kind: 'all' },\n      }\n      : undefined;\n\n  return new ChatGenerationChunk({\n    text,\n    message: new AIMessageChunk({\n      content: content,\n      name: !candidateContent ? undefined : candidateContent.role,\n      tool_call_chunks: toolCallChunks,\n      // Each chunk can have unique \"generationInfo\", and merging strategy is unclear,\n      // so leave blank for now.\n      additional_kwargs,\n      response_metadata,\n      usage_metadata: isFinalChunk ? extra.usageMetadata : undefined,\n    }),\n    generationInfo,\n  });\n}\n\n/**\n * Maps a Google GenerateContentResult to a LangChain ChatResult\n */\nexport function mapGenerateContentResultToChatResult(\n  response: EnhancedGenerateContentResponse,\n  extra?: {\n    usageMetadata: UsageMetadata | undefined;\n  }\n): ChatResult {\n  if (!response.candidates || response.candidates.length === 0) {\n    return {\n      generations: [],\n      llmOutput: {\n        filters: response.promptFeedback,\n      },\n    };\n  }\n  const [candidate] = response.candidates as [\n    Partial<GenerateContentCandidate> | undefined,\n  ];\n  const { content: candidateContent, ...generationInfo } = candidate ?? {};\n\n  // Extract function calls directly from parts to preserve thoughtSignature\n  const functionCalls =\n    candidateContent?.parts.reduce(\n      (acc, p) => {\n        if ('functionCall' in p && p.functionCall) {\n          acc.push({\n            ...p,\n            id:\n              'id' in p.functionCall && typeof p.functionCall.id === 'string'\n                ? p.functionCall.id\n                : uuidv4(),\n          });\n        }\n        return acc;\n      },\n      [] as (FunctionCallPart & { id: string; thoughtSignature?: string })[]\n    ) ?? [];\n\n  let content: MessageContent | undefined;\n  const reasoningParts: string[] = [];\n  if (\n    Array.isArray(candidateContent?.parts) &&\n    candidateContent.parts.length === 1 &&\n    (candidateContent.parts[0].text ?? '') !== '' &&\n    !(\n      'thought' in candidateContent.parts[0] &&\n      candidateContent.parts[0].thought === true\n    )\n  ) {\n    content = candidateContent.parts[0].text;\n  } else if (\n    Array.isArray(candidateContent?.parts) &&\n    candidateContent.parts.length > 0\n  ) {\n    content = toLangChainContent(\n      candidateContent.parts\n        .map((p) => {\n          if ('text' in p && 'thought' in p && p.thought === true) {\n            reasoningParts.push(p.text ?? '');\n            return undefined;\n          } else if ('text' in p) {\n            return {\n              type: 'text',\n              text: p.text,\n            };\n          } else if ('executableCode' in p) {\n            return {\n              type: 'executableCode',\n              executableCode: p.executableCode,\n            };\n          } else if ('codeExecutionResult' in p) {\n            return {\n              type: 'codeExecutionResult',\n              codeExecutionResult: p.codeExecutionResult,\n            };\n          }\n          const serverSideToolPart = convertGoogleServerSideToolResponsePart(p);\n          if (serverSideToolPart !== undefined) {\n            return serverSideToolPart;\n          }\n          return p;\n        })\n        .filter((p) => p !== undefined)\n    );\n  } else {\n    content = [];\n  }\n  let text = '';\n  if (typeof content === 'string') {\n    text = content;\n  } else if (Array.isArray(content) && content.length > 0) {\n    const block = content.find((b) => 'text' in b) as\n      | { text: string }\n      | undefined;\n    text = block?.text ?? text;\n  }\n\n  const additional_kwargs: ChatGeneration['message']['additional_kwargs'] = {\n    ...generationInfo,\n  };\n  if (reasoningParts.length > 0) {\n    additional_kwargs.reasoning = reasoningParts.join('');\n  }\n\n  // Extract thought signatures from function calls for Gemini 3+\n  const functionThoughtSignatures = functionCalls.reduce(\n    (acc, fc) => {\n      if ('thoughtSignature' in fc && typeof fc.thoughtSignature === 'string') {\n        acc[fc.id] = fc.thoughtSignature;\n      }\n      return acc;\n    },\n    {} as Record<string, string>\n  );\n\n  const tool_calls = functionCalls.map((fc) => ({\n    type: 'tool_call' as const,\n    id: fc.id,\n    name: fc.functionCall.name,\n    args: fc.functionCall.args,\n  }));\n\n  // Store thought signatures map for later retrieval\n  additional_kwargs[_FUNCTION_CALL_THOUGHT_SIGNATURES_MAP_KEY] =\n    functionThoughtSignatures;\n\n  const generation: ChatGeneration = {\n    text,\n    message: new AIMessage({\n      content,\n      tool_calls,\n      additional_kwargs,\n      usage_metadata: extra?.usageMetadata,\n    }),\n    generationInfo,\n  };\n  return {\n    generations: [generation],\n    llmOutput: {\n      tokenUsage: {\n        promptTokens: extra?.usageMetadata?.input_tokens,\n        completionTokens: extra?.usageMetadata?.output_tokens,\n        totalTokens: extra?.usageMetadata?.total_tokens,\n      },\n    },\n  };\n}\n\nexport function convertToGenerativeAITools(\n  tools: GoogleGenerativeAIToolType[]\n): GoogleGenerativeAIFunctionDeclarationsTool[] {\n  if (\n    tools.every(\n      (tool) =>\n        'functionDeclarations' in tool &&\n        Array.isArray(tool.functionDeclarations)\n    )\n  ) {\n    return tools as GoogleGenerativeAIFunctionDeclarationsTool[];\n  }\n  return [\n    {\n      functionDeclarations: tools.map(\n        (tool): GenerativeAIFunctionDeclaration => {\n          if (isLangChainTool(tool)) {\n            const jsonSchema = schemaToGenerativeAIParameters(tool.schema);\n            if (\n              jsonSchema.type === 'object' &&\n              'properties' in jsonSchema &&\n              Object.keys(jsonSchema.properties).length === 0\n            ) {\n              return {\n                name: tool.name,\n                description: tool.description,\n              };\n            }\n            return {\n              name: tool.name,\n              description: tool.description,\n              parameters: jsonSchema,\n            };\n          }\n          if (isOpenAITool(tool)) {\n            return {\n              name: tool.function.name,\n              description:\n                tool.function.description ?? 'A function available to call.',\n              parameters: jsonSchemaToGeminiParameters(\n                tool.function.parameters\n              ),\n            };\n          }\n          return tool as unknown as GenerativeAIFunctionDeclaration;\n        }\n      ),\n    },\n  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package/dist/types/llm/google/utils/common.d.ts

@@ -21,6 +21,15 @@ export declare function getMessageAuthor(message: BaseMessage): string;
 export declare function convertAuthorToRole(author: string): (typeof POSSIBLE_ROLES)[number];
 export declare function convertMessageContentToParts(message: BaseMessage, isMultimodalModel: boolean, previousMessages: BaseMessage[], model?: string): Part[];
 export declare function convertBaseMessagesToContent(messages: BaseMessage[], isMultimodalModel: boolean, convertSystemMessageToHumanContent?: boolean, model?: string): Content[] | undefined;
+export declare function rejectsModelTurnPrefill(model?: string): boolean;
+/**
+ * Drops trailing `model`-role turns for models that reject prefill (see
+ * {@link rejectsModelTurnPrefill}). Such a turn is only produced by prefill
+ * flows (e.g. editing an assistant reply and resubmitting); these models return
+ * HTTP 400 for it, so we drop it and let the model generate fresh from the
+ * preceding user turn. No-op for every other model, preserving working prefill.
+ */
+export declare function dropUnsupportedModelTurnPrefill(contents: Content[] | undefined, model?: string): Content[] | undefined;
 export declare function convertResponseContentToChatGenerationChunk(response: EnhancedGenerateContentResponse, extra: {
     usageMetadata?: UsageMetadata | undefined;
     index: number;

package/package.json

@@ -1,6 +1,6 @@
 {
   "name": "@librechat/agents",
-  "version": "3.2.67",
+  "version": "3.2.68",
   "main": "./dist/cjs/main.cjs",
   "module": "./dist/esm/main.mjs",
   "types": "./dist/types/index.d.ts",

package/src/llm/google/index.ts

@@ -19,6 +19,7 @@ import type { GoogleClientOptions, GoogleThinkingConfig } from '@/types';
 import {
   convertResponseContentToChatGenerationChunk,
   convertBaseMessagesToContent,
+  dropUnsupportedModelTurnPrefill,
   mapGenerateContentResultToChatResult,
 } from './utils/common';
 
@@ -254,6 +255,7 @@ export class CustomChatGoogleGenerativeAI extends ChatGoogleGenerativeAI {
       this.client.systemInstruction = systemInstruction;
       actualPrompt = prompt.slice(1);
     }
+    actualPrompt = dropUnsupportedModelTurnPrefill(actualPrompt, this.model);
     const parameters = this.invocationParams(options);
     const request = {
       ...parameters,
@@ -308,6 +310,7 @@ export class CustomChatGoogleGenerativeAI extends ChatGoogleGenerativeAI {
       this.client.systemInstruction = systemInstruction;
       actualPrompt = prompt.slice(1);
     }
+    actualPrompt = dropUnsupportedModelTurnPrefill(actualPrompt, this.model);
     const parameters = this.invocationParams(options);
     const request = {
       ...parameters,

package/src/llm/google/utils/common.test.ts

@@ -1,12 +1,16 @@
 import { expect, test, describe } from '@jest/globals';
 import { AIMessageChunk } from '@langchain/core/messages';
-import type { EnhancedGenerateContentResponse } from '@google/generative-ai';
+import type { Content, EnhancedGenerateContentResponse } from '@google/generative-ai';
 import {
   STREAMED_TOOL_CALL_SEAL_METADATA_KEY,
   STREAMED_TOOL_CALL_ADAPTER_METADATA_KEY,
   GOOGLE_STREAMED_TOOL_CALL_ADAPTER,
 } from '@/tools/streamedToolCallSeals';
-import { convertResponseContentToChatGenerationChunk } from './common';
+import {
+  convertResponseContentToChatGenerationChunk,
+  dropUnsupportedModelTurnPrefill,
+  rejectsModelTurnPrefill,
+} from './common';
 
 function buildResponse(
   parts: Array<Record<string, unknown>>
@@ -62,3 +66,54 @@ describe('convertResponseContentToChatGenerationChunk seal metadata', () => {
     expect(metadata[STREAMED_TOOL_CALL_SEAL_METADATA_KEY]).toBeUndefined();
   });
 });
+
+describe('rejectsModelTurnPrefill', () => {
+  test('is true for models that reject a trailing model turn', () => {
+    expect(rejectsModelTurnPrefill('gemini-3.6-flash')).toBe(true);
+    expect(rejectsModelTurnPrefill('gemini-3.5-flash-lite')).toBe(true);
+    expect(rejectsModelTurnPrefill('models/gemini-3.6-flash')).toBe(true);
+    expect(rejectsModelTurnPrefill('google/gemini-3.5-flash-lite-latest')).toBe(true);
+  });
+
+  test('is false for models that still accept prefill and for empty input', () => {
+    expect(rejectsModelTurnPrefill('gemini-3.5-flash')).toBe(false);
+    expect(rejectsModelTurnPrefill('gemini-2.5-flash')).toBe(false);
+    expect(rejectsModelTurnPrefill('gemini-3-pro-preview')).toBe(false);
+    expect(rejectsModelTurnPrefill(undefined)).toBe(false);
+    expect(rejectsModelTurnPrefill('')).toBe(false);
+  });
+});
+
+describe('dropUnsupportedModelTurnPrefill', () => {
+  const userTurn: Content = { role: 'user', parts: [{ text: 'Hi' }] };
+  const modelTurn: Content = { role: 'model', parts: [{ text: 'Hello, I am' }] };
+
+  test('drops a trailing model turn for no-prefill models', () => {
+    const contents: Content[] = [userTurn, modelTurn];
+    const result = dropUnsupportedModelTurnPrefill(contents, 'gemini-3.6-flash');
+    expect(result).toEqual([userTurn]);
+  });
+
+  test('drops multiple consecutive trailing model turns but keeps one turn', () => {
+    const contents: Content[] = [userTurn, modelTurn, modelTurn];
+    const result = dropUnsupportedModelTurnPrefill(contents, 'gemini-3.5-flash-lite');
+    expect(result).toEqual([userTurn]);
+  });
+
+  test('leaves a trailing model turn for models that accept prefill', () => {
+    const contents: Content[] = [userTurn, modelTurn];
+    const result = dropUnsupportedModelTurnPrefill(contents, 'gemini-3.5-flash');
+    expect(result).toBe(contents);
+  });
+
+  test('is a no-op when the request already ends with a user turn', () => {
+    const contents: Content[] = [modelTurn, userTurn];
+    const result = dropUnsupportedModelTurnPrefill(contents, 'gemini-3.6-flash');
+    expect(result).toBe(contents);
+  });
+
+  test('is a no-op for empty or undefined contents', () => {
+    expect(dropUnsupportedModelTurnPrefill([], 'gemini-3.6-flash')).toEqual([]);
+    expect(dropUnsupportedModelTurnPrefill(undefined, 'gemini-3.6-flash')).toBeUndefined();
+  });
+});

package/src/llm/google/utils/common.ts

@@ -631,6 +631,50 @@ export function convertBaseMessagesToContent(
   ).content;
 }
 
+/**
+ * Gemini models that reject a request whose `contents` end with a `model`-role
+ * turn (a "prefill"). Google enforces this on newer generations (Gemini 3.6
+ * Flash, Gemini 3.5 Flash-Lite) while older/sibling models still accept a
+ * trailing model turn, so the rule is model-scoped rather than version-wide.
+ * Extend this list as Google applies the restriction to further models.
+ * @see https://ai.google.dev/gemini-api/docs/latest-model#api-changes-and-parameter-updates
+ */
+const NO_PREFILL_GEMINI_MODELS = [
+  'gemini-3.6-flash',
+  'gemini-3.5-flash-lite',
+] as const;
+
+export function rejectsModelTurnPrefill(model?: string): boolean {
+  if (model == null || model === '') {
+    return false;
+  }
+  const modelId = model.toLowerCase().split('/').pop() ?? '';
+  return NO_PREFILL_GEMINI_MODELS.some(
+    (id) => modelId === id || modelId.startsWith(`${id}-`)
+  );
+}
+
+/**
+ * Drops trailing `model`-role turns for models that reject prefill (see
+ * {@link rejectsModelTurnPrefill}). Such a turn is only produced by prefill
+ * flows (e.g. editing an assistant reply and resubmitting); these models return
+ * HTTP 400 for it, so we drop it and let the model generate fresh from the
+ * preceding user turn. No-op for every other model, preserving working prefill.
+ */
+export function dropUnsupportedModelTurnPrefill(
+  contents: Content[] | undefined,
+  model?: string
+): Content[] | undefined {
+  if (contents == null || contents.length === 0 || !rejectsModelTurnPrefill(model)) {
+    return contents;
+  }
+  let end = contents.length;
+  while (end > 1 && contents[end - 1]?.role === 'model') {
+    end -= 1;
+  }
+  return end === contents.length ? contents : contents.slice(0, end);
+}
+
 export function convertResponseContentToChatGenerationChunk(
   response: EnhancedGenerateContentResponse,
   extra: {