punctilio 3.1.0 → 3.1.2

package/dist/constants.d.ts

@@ -98,17 +98,21 @@ export declare const TERMINAL_PUNCTUATION: readonly ["!", "?", ".", ",", ";", ":
  */
 export declare const LATIN_LETTERS = "A-Za-z\\u00C0-\\u00D6\\u00D8-\\u00F6\\u00F8-\\u00FF\\u0100-\\u017F\\u0180-\\u024F";
 /**
- * Default separator character for text spanning HTML elements.
- * Uses Unicode Private Use Area character U+E000.
+ * Default separator for text spanning HTML elements.
+ * Uses a two-character sentinel from the Unicode Private Use Area
+ * (U+E000 U+E001) to avoid collisions with CJK fonts, Apple emoji
+ * internals, PDF-to-text output, and icon fonts that repurpose U+E000.
  */
-export declare const DEFAULT_SEPARATOR = "\uE000";
+export declare const DEFAULT_SEPARATOR = "\uE000\uE001";
 export declare const ESCAPED_DEFAULT_SEPARATOR: string;
 /**
- * Returns the regex-escaped separator string for the given options.
- * Centralizes the common pattern of falling back to the pre-escaped default.
+ * Returns the regex-escaped separator string for the given options,
+ * wrapped in a non-capturing group so that quantifiers like `?` and `*`
+ * apply to the entire separator sequence (critical for multi-character
+ * separators like the default U+E000 U+E001).
  *
  * @param options - Object with an optional `separator` field
- * @returns Regex-escaped separator string
+ * @returns Regex-escaped separator string wrapped in `(?:...)`
  */
 export declare function getEscapedSeparator(options: {
     separator?: string;
@@ -161,16 +165,22 @@ export declare const SPACE_CHARS: string;
  * Creates a lookbehind pattern that matches after whitespace, separator, or start of string.
  * Used for arrow patterns and other constructs that should appear at word boundaries.
  *
- * @param escapedSeparator - Regex-escaped separator string
- * @returns Pattern string: `(?<=[\\s${sep}]|^)`
+ * Uses alternation instead of a character class so that multi-character
+ * separators are matched as a sequence, not as individual characters.
+ *
+ * @param escapedSeparator - Regex-escaped separator string (may be grouped)
+ * @returns Pattern string: `(?<=\\s|${sep}|^)`
  */
 export declare function spaceBoundaryStart(escapedSeparator: string): string;
 /**
  * Creates a lookahead pattern that matches before whitespace, separator, or end of string.
  * Used for arrow patterns and other constructs that should appear at word boundaries.
  *
- * @param escapedSeparator - Regex-escaped separator string
- * @returns Pattern string: `(?=[\\s${sep}]|$)`
+ * Uses alternation instead of a character class so that multi-character
+ * separators are matched as a sequence, not as individual characters.
+ *
+ * @param escapedSeparator - Regex-escaped separator string (may be grouped)
+ * @returns Pattern string: `(?=\\s|${sep}|$)`
  */
 export declare function spaceBoundaryEnd(escapedSeparator: string): string;
 /**

package/dist/constants.d.ts.map

@@ -1 +1 @@
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+{"version":3,"file":"constants.d.ts","sourceRoot":"","sources":["../src/constants.ts"],"names":[],"mappings":"AAAA;;;;;;;;GAQG;AAIH;;GAEG;AACH,eAAO,MAAM,eAAe;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;CAuElB,CAAA;AAEV;;;;;;GAMG;AACH,eAAO,MAAM,oBAAoB,8HAYvB,CAAA;AAEV;;;;;;;;;;;GAWG;AACH,eAAO,MAAM,aAAa,sFAAsF,CAAA;AAEhH;;;;;GAKG;AACH,eAAO,MAAM,iBAAiB,iBAAiB,CAAA;AAC/C,eAAO,MAAM,yBAAyB,QAAwC,CAAA;AAE9E;;;;;;;;GAQG;AACH,wBAAgB,mBAAmB,CAAC,OAAO,EAAE;IAAE,SAAS,CAAC,EAAE,MAAM,CAAA;CAAE,GAAG,MAAM,CAK3E;AAED;;;GAGG;AACH,eAAO,MAAM,mBAAmB,wEAAyE,CAAA;AAEzG;;;;;;;;;;;;;;;GAeG;AACH,wBAAgB,iBAAiB,CAAC,gBAAgB,EAAE,MAAM,GAAG,MAAM,CAElE;AAED;;;;;;;;;;;;;;;GAeG;AACH,wBAAgB,eAAe,CAAC,gBAAgB,EAAE,MAAM,GAAG,MAAM,CAEhE;AAED;;;GAGG;AACH,eAAO,MAAM,WAAW,QAA6B,CAAA;AAErD;;;;;;;;;GASG;AACH,wBAAgB,kBAAkB,CAAC,gBAAgB,EAAE,MAAM,GAAG,MAAM,CAEnE;AAED;;;;;;;;;GASG;AACH,wBAAgB,gBAAgB,CAAC,gBAAgB,EAAE,MAAM,GAAG,MAAM,CAEjE;AAUD;;;;GAIG;AACH,wBAAgB,YAAY,CAAC,OAAO,EAAE,MAAM,EAAE,KAAK,EAAE,MAAM,GAAG,MAAM,CAcnE"}

package/dist/constants.js

@@ -117,22 +117,27 @@ export const TERMINAL_PUNCTUATION = [
  */
 export const LATIN_LETTERS = "A-Za-z\\u00C0-\\u00D6\\u00D8-\\u00F6\\u00F8-\\u00FF\\u0100-\\u017F\\u0180-\\u024F";
 /**
- * Default separator character for text spanning HTML elements.
- * Uses Unicode Private Use Area character U+E000.
+ * Default separator for text spanning HTML elements.
+ * Uses a two-character sentinel from the Unicode Private Use Area
+ * (U+E000 U+E001) to avoid collisions with CJK fonts, Apple emoji
+ * internals, PDF-to-text output, and icon fonts that repurpose U+E000.
  */
-export const DEFAULT_SEPARATOR = "\uE000";
+export const DEFAULT_SEPARATOR = "\uE000\uE001";
 export const ESCAPED_DEFAULT_SEPARATOR = escapeStringRegexp(DEFAULT_SEPARATOR);
 /**
- * Returns the regex-escaped separator string for the given options.
- * Centralizes the common pattern of falling back to the pre-escaped default.
+ * Returns the regex-escaped separator string for the given options,
+ * wrapped in a non-capturing group so that quantifiers like `?` and `*`
+ * apply to the entire separator sequence (critical for multi-character
+ * separators like the default U+E000 U+E001).
  *
  * @param options - Object with an optional `separator` field
- * @returns Regex-escaped separator string
+ * @returns Regex-escaped separator string wrapped in `(?:...)`
  */
 export function getEscapedSeparator(options) {
-    return options.separator
+    const escaped = options.separator
         ? escapeStringRegexp(options.separator)
         : ESCAPED_DEFAULT_SEPARATOR;
+    return `(?:${escaped})`;
 }
 /**
  * Characters that have special meaning in regular expressions.
@@ -186,21 +191,27 @@ export const SPACE_CHARS = ` ${UNICODE_SYMBOLS.NBSP}`;
  * Creates a lookbehind pattern that matches after whitespace, separator, or start of string.
  * Used for arrow patterns and other constructs that should appear at word boundaries.
  *
- * @param escapedSeparator - Regex-escaped separator string
- * @returns Pattern string: `(?<=[\\s${sep}]|^)`
+ * Uses alternation instead of a character class so that multi-character
+ * separators are matched as a sequence, not as individual characters.
+ *
+ * @param escapedSeparator - Regex-escaped separator string (may be grouped)
+ * @returns Pattern string: `(?<=\\s|${sep}|^)`
  */
 export function spaceBoundaryStart(escapedSeparator) {
-    return `(?<=[\\s${escapedSeparator}]|^)`;
+    return `(?<=\\s|${escapedSeparator}|^)`;
 }
 /**
  * Creates a lookahead pattern that matches before whitespace, separator, or end of string.
  * Used for arrow patterns and other constructs that should appear at word boundaries.
  *
- * @param escapedSeparator - Regex-escaped separator string
- * @returns Pattern string: `(?=[\\s${sep}]|$)`
+ * Uses alternation instead of a character class so that multi-character
+ * separators are matched as a sequence, not as individual characters.
+ *
+ * @param escapedSeparator - Regex-escaped separator string (may be grouped)
+ * @returns Pattern string: `(?=\\s|${sep}|$)`
  */
 export function spaceBoundaryEnd(escapedSeparator) {
-    return `(?=[\\s${escapedSeparator}]|$)`;
+    return `(?=\\s|${escapedSeparator}|$)`;
 }
 /**
  * Cache for compiled RegExp objects keyed by `pattern + '\0' + flags`.

package/dist/constants.js.map

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package/dist/dashes.d.ts.map

@@ -1 +1 @@
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package/dist/dashes.js

@@ -1,7 +1,6 @@
 /**
  * Dash transformation: hyphens → em-dashes, en-dashes, minus signs.
  */
-import escapeStringRegexp from "escape-string-regexp";
 import { UNICODE_SYMBOLS, DEFAULT_SEPARATOR, LATIN_LETTERS, wordBoundaryStart, wordBoundaryEnd, getEscapedSeparator, cachedRegExp } from "./constants.js";
 const { EN_DASH, EM_DASH, MINUS, LEFT_DOUBLE_QUOTE, RIGHT_DOUBLE_QUOTE, LEFT_SINGLE_QUOTE, RIGHT_SINGLE_QUOTE } = UNICODE_SYMBOLS;
 /**
@@ -102,7 +101,7 @@ export function minusReplace(text, options = {}) {
 function convertParentheticalDashes(text, sep, style) {
     const localizedDash = style === "british" ? EN_DASH : EM_DASH;
     const maybeSpace = style === "british" ? " " : "";
-    const escapedSep = escapeStringRegexp(sep);
+    const escapedSep = getEscapedSeparator({ separator: sep });
     // Convert spaced dashes: "word - word" or "word — word"
     // When a separator follows the dash, preserve trailing spaces (they belong to the next text segment).
     // A single plain hyphen directly before a word character (through optional separators) is a
@@ -137,7 +136,7 @@ function convertParentheticalDashes(text, sep, style) {
  * allows a space after the dash: "Don't inter— Hey! Who threw that?"
  */
 function normalizeEmDashSpacing(text, sep) {
-    const escapedSep = escapeStringRegexp(sep);
+    const escapedSep = getEscapedSeparator({ separator: sep });
     // Remove all spaces around em-dashes
     text = text.replace(cachedRegExp(`(?<before>${escapedSep}?)[ ]*${EM_DASH}[ ]*(?<after>${escapedSep}?)`, "g"), `$<before>${EM_DASH}$<after>`);
     // Preserve space after em-dash at start of line (e.g., attribution)

package/dist/dashes.js.map

@@ -1 +1 @@
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+{"version":3,"file":"index.d.ts","sourceRoot":"","sources":["../src/index.ts"],"names":[],"mappings":"AAAA;;;;;;;;GAQG;AAEH,OAAO,EAAE,UAAU,EAAE,mBAAmB,EAAE,KAAK,YAAY,EAAE,KAAK,gBAAgB,EAAE,MAAM,aAAa,CAAA;AACvG,OAAO,KAAK,EAAE,gBAAgB,EAAE,MAAM,aAAa,CAAA;AACnD,OAAO,EACL,aAAa,EACb,iBAAiB,EACjB,eAAe,EACf,YAAY,EACZ,MAAM,EACN,6BAA6B,EAC7B,KAAK,WAAW,EAChB,KAAK,SAAS,GACf,MAAM,aAAa,CAAA;AACpB,OAAO,KAAK,EAAE,SAAS,EAAE,MAAM,aAAa,CAAA;AAC5C,OAAO,EACL,QAAQ,EACR,cAAc,EACd,WAAW,EACX,YAAY,EACZ,MAAM,EACN,OAAO,EACP,SAAS,EACT,UAAU,EACV,cAAc,EACd,kBAAkB,EAClB,oBAAoB,EACpB,eAAe,EACf,KAAK,aAAa,GACnB,MAAM,cAAc,CAAA;AACrB,OAAO,EACL,mBAAmB,EACnB,wBAAwB,EACxB,kBAAkB,EAClB,+BAA+B,EAC/B,uBAAuB,EACvB,mBAAmB,EACnB,yBAAyB,EACzB,mBAAmB,EACnB,aAAa,EACb,KAAK,EACL,UAAU,EACV,uBAAuB,EACvB,KAAK,WAAW,GACjB,MAAM,WAAW,CAAA;AAElB,MAAM,WAAW,gBAAgB;IAC/B;;;;;;;OAOG;IACH,SAAS,CAAC,EAAE,MAAM,CAAA;IAElB;;;OAGG;IACH,OAAO,CAAC,EAAE,OAAO,CAAA;IAEjB;;;;;;;;OAQG;IACH,cAAc,CAAC,EAAE,OAAO,CAAA;IAExB;;;;;;;;;;;;;;;;;OAiBG;IACH,gBAAgB,CAAC,EAAE,gBAAgB,CAAA;IAEnC;;;;;;;;;;;;;OAaG;IACH,SAAS,CAAC,EAAE,SAAS,CAAA;IAErB;;;OAGG;IACH,SAAS,CAAC,EAAE,OAAO,CAAA;IAEnB;;;OAGG;IACH,OAAO,CAAC,EAAE,OAAO,CAAA;IAEjB;;;;OAIG;IACH,WAAW,CAAC,EAAE,OAAO,CAAA;IAErB;;;;OAIG;IACH,SAAS,CAAC,EAAE,OAAO,CAAA;IAEnB;;;;;OAKG;IACH,IAAI,CAAC,EAAE,OAAO,CAAA;IAEd;;;;;;OAMG;IACH,gBAAgB,CAAC,EAAE,OAAO,CAAA;CAE3B;AASD,OAAO,EAAE,qBAAqB,EAAE,6BAA6B,EAAE,eAAe,EAAE,MAAM,YAAY,CAAA;AAClG,OAAO,EAAE,iBAAiB,EAAE,eAAe,EAAE,MAAM,gBAAgB,CAAA;AACnE,eAAO,MAAM,0BAA0B,KAA6C,CAAA;AAiDpF,wBAAgB,SAAS,CAAC,IAAI,EAAE,MAAM,EAAE,OAAO,GAAE,gBAAqB,GAAG,MAAM,CAwE9E"}

package/dist/index.js

@@ -68,12 +68,17 @@ const defaultOpts = {
 };
 export function transform(text, options = {}) {
     const separator = options.separator ?? DEFAULT_SEPARATOR;
-    // Validate separator: must be a single UTF-16 code unit (BMP character)
-    // Multi-codepoint characters (surrogate pairs like emoji) cause issues with regex patterns
-    if (separator.length !== 1) {
-        throw new Error(`Invalid separator: must be a single character. ` +
-            `Received "${separator}" (length: ${separator.length}). ` +
-            `Use a single-codepoint character like the default "\\uE000".`);
+    // Validate separator: must be non-empty and contain only BMP characters.
+    // for...of iterates by code point; surrogate pairs (non-BMP) yield a
+    // two-UTF16-unit string, so ch.length > 1 detects them.
+    if (separator.length === 0) {
+        throw new Error("Invalid separator: must not be empty.");
+    }
+    for (const ch of separator) {
+        if (ch.length > 1) {
+            throw new Error(`Invalid separator: must contain only BMP characters (no characters outside the Basic Multilingual Plane). ` +
+                `Received "${separator}" which contains a non-BMP character.`);
+        }
     }
     const original = text;
     const { symbols, fractions, degrees, superscript, ligatures, nbsp, collapseSpaces, checkIdempotency, ...separatorOpts } = { ...defaultOpts, ...options };

package/dist/index.js.map

@@ -1 +1 @@
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package/dist/nbsp.d.ts.map

@@ -1 +1 @@
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+{"version":3,"file":"nbsp.d.ts","sourceRoot":"","sources":["../src/nbsp.ts"],"names":[],"mappings":"AAAA;;;;;;;;GAQG;AAGH,OAAO,KAAK,EAAE,aAAa,EAAE,MAAM,cAAc,CAAA;AAajD,MAAM,MAAM,WAAW,GAAG,IAAI,CAAC,aAAa,EAAE,WAAW,CAAC,CAAA;AAO1D;;;GAGG;AACH,eAAO,MAAM,KAAK,UA2BjB,CAAA;AAED,eAAO,MAAM,UAAU,UActB,CAAA;AAED,eAAO,MAAM,uBAAuB,UASnC,CAAA;AASD;;;;;GAKG;AACH,wBAAgB,mBAAmB,CAAC,IAAI,EAAE,MAAM,EAAE,OAAO,GAAE,WAAgB,GAAG,MAAM,CAOnF;AAED;;;;GAIG;AACH,wBAAgB,wBAAwB,CAAC,IAAI,EAAE,MAAM,EAAE,OAAO,GAAE,WAAgB,GAAG,MAAM,CAQxF;AAED;;;;;;GAMG;AACH,wBAAgB,kBAAkB,CAAC,IAAI,EAAE,MAAM,EAAE,OAAO,GAAE,WAAgB,GAAG,MAAM,CAQlF;AAED;;;;;GAKG;AACH,wBAAgB,+BAA+B,CAAC,IAAI,EAAE,MAAM,EAAE,OAAO,GAAE,WAAgB,GAAG,MAAM,CAO/F;AAED;;;;;GAKG;AACH,wBAAgB,uBAAuB,CAAC,IAAI,EAAE,MAAM,EAAE,OAAO,GAAE,WAAgB,GAAG,MAAM,CAOvF;AAED;;;;GAIG;AACH,wBAAgB,mBAAmB,CAAC,IAAI,EAAE,MAAM,EAAE,OAAO,GAAE,WAAgB,GAAG,MAAM,CAOnF;AAED;;;;;GAKG;AACH,wBAAgB,yBAAyB,CAAC,IAAI,EAAE,MAAM,EAAE,OAAO,GAAE,WAAgB,GAAG,MAAM,CAOzF;AAED;;;;GAIG;AACH,wBAAgB,mBAAmB,CAAC,IAAI,EAAE,MAAM,EAAE,OAAO,GAAE,WAAgB,GAAG,MAAM,CAOnF;AAsBD,gEAAgE;AAChE,wBAAgB,aAAa,CAAC,IAAI,EAAE,MAAM,EAAE,OAAO,GAAE,WAAgB,GAAG,MAAM,CAK7E"}

package/dist/nbsp.js

@@ -106,7 +106,8 @@ export function nbspBetweenNumberAndUnit(text, options = {}) {
  */
 export function nbspBeforeLastWord(text, options = {}) {
     const sep = getEscapedSeparator(options);
-    const pattern = cachedRegExp(`(?<=[\\w${sep}])${SPACE}(?<lastWord>[^\\s${sep}]{1,10})(?<ending>${sep}?(?:\\n\\n|$))`, "g");
+    // Use alternation instead of character classes for multi-char separator support
+    const pattern = cachedRegExp(`(?<=\\w|${sep})${SPACE}(?<lastWord>(?:(?!\\s)(?!${sep}).){1,10})(?<ending>${sep}?(?:\\n\\n|$))`, "g");
     return text.replace(pattern, `${NBSP}$<lastWord>$<ending>`);
 }
 /**

package/dist/nbsp.js.map

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+{"version":3,"file":"quotes.d.ts","sourceRoot":"","sources":["../src/quotes.ts"],"names":[],"mappings":"AAAA;;GAEG;AAiBH,MAAM,MAAM,gBAAgB,GAAG,UAAU,GAAG,SAAS,GAAG,QAAQ,GAAG,QAAQ,GAAG,MAAM,CAAA;AAEpF,MAAM,WAAW,YAAY;IAC3B,qEAAqE;IACrE,SAAS,CAAC,EAAE,MAAM,CAAA;IAClB,4EAA4E;IAC5E,gBAAgB,CAAC,EAAE,gBAAgB,CAAA;CACpC;AA+OD,+CAA+C;AAC/C,wBAAgB,UAAU,CAAC,IAAI,EAAE,MAAM,EAAE,OAAO,GAAE,YAAiB,GAAG,MAAM,CAK3E;AAED;;;;;;;;;GASG;AACH,wBAAgB,mBAAmB,CAAC,IAAI,EAAE,MAAM,EAAE,OAAO,GAAE,YAAiB,GAAG,MAAM,CAEpF"}

package/dist/quotes.js

@@ -2,13 +2,13 @@
  * Smart quote transformation: straight quotes → curly quotes.
  */
 import escapeStringRegexp from "escape-string-regexp";
-import { UNICODE_SYMBOLS, DEFAULT_SEPARATOR, LATIN_LETTERS, TERMINAL_PUNCTUATION, cachedRegExp } from "./constants.js";
+import { UNICODE_SYMBOLS, DEFAULT_SEPARATOR, LATIN_LETTERS, TERMINAL_PUNCTUATION, getEscapedSeparator, cachedRegExp } from "./constants.js";
 const { EM_DASH, LEFT_DOUBLE_QUOTE, RIGHT_DOUBLE_QUOTE, LEFT_SINGLE_QUOTE, RIGHT_SINGLE_QUOTE, MODIFIER_LETTER_APOSTROPHE, } = UNICODE_SYMBOLS;
 /** Joined string of all terminal punctuation characters for use in regex character classes. */
 const TERMINAL_PUNCTUATION_CLASS = TERMINAL_PUNCTUATION.join("");
 /** Convert straight single quotes to curly quotes and apostrophes */
 function convertSingleQuotes(text, sep) {
-    const escapedSep = escapeStringRegexp(sep);
+    const escapedSep = getEscapedSeparator({ separator: sep });
     // Handle empty single quotes '' and whitespace-only quotes ' ' first
     // Only match straight quotes, not already-converted curly quotes
     const singleQuoteChars = `'${LEFT_SINGLE_QUOTE}${RIGHT_SINGLE_QUOTE}${MODIFIER_LETTER_APOSTROPHE}`;
@@ -60,8 +60,9 @@ function convertUnmatchedPluralPossessives(text, sep) {
             return match;
         }
         let i = offset - 1;
-        while (i >= 0 && text[i] === sep)
-            i--;
+        while (i >= sep.length - 1 && text.startsWith(sep, i - sep.length + 1)) {
+            i -= sep.length;
+        }
         if (i >= 0 && (text[i] === "s" || text[i] === "S")) {
             return MODIFIER_LETTER_APOSTROPHE;
         }
@@ -70,13 +71,14 @@ function convertUnmatchedPluralPossessives(text, sep) {
 }
 /** Convert straight double quotes to curly quotes */
 function convertDoubleQuotes(text, sep) {
-    const escapedSep = escapeStringRegexp(sep);
+    const rawEscSep = escapeStringRegexp(sep);
+    const escapedSep = getEscapedSeparator({ separator: sep });
     // Handle empty quotes "" first - match only when not part of adjacent quotes
     // Require word boundary or start/end of string on at least one side
     text = text.replace(/(?<=^|[\s([{])""(?=$|[\s)\]}.!?,;:])/g, `${LEFT_DOUBLE_QUOTE}${RIGHT_DOUBLE_QUOTE}`);
     // Handle whitespace-only quotes " " - require non-quote chars on both sides
     text = text.replace(/(?<=^|[\s([{])"(?<whitespace>\s+)"(?=$|[\s)\]}.!?,;:])/g, `${LEFT_DOUBLE_QUOTE}$<whitespace>${RIGHT_DOUBLE_QUOTE}`);
-    const beginningDouble = cachedRegExp(`(?<=^|[\\s\\(\\/\\[\\{\\-${EM_DASH}${escapedSep}])(?<beforeChr>${escapedSep}?)["](?<afterChr>(?<sepWithPunct>${escapedSep}[ .,])|(?=${escapedSep}?\\.{3}|${escapedSep}?[^\\s\\)\\${EM_DASH},!?${escapedSep};:.\\}]))`, "gm");
+    const beginningDouble = cachedRegExp(`(?<=^|[\\s\\(\\/\\[\\{\\-${EM_DASH}]|${escapedSep})(?<beforeChr>${escapedSep}?)["](?<afterChr>(?<sepWithPunct>${escapedSep}[ .,])|(?=${escapedSep}?\\.{3}|${escapedSep}?[^\\s\\)${EM_DASH},!?;:.\\}${rawEscSep}]))`, "gm");
     text = text.replace(beginningDouble, `$<beforeChr>${LEFT_DOUBLE_QUOTE}$<afterChr>`);
     text = text.replace(cachedRegExp(`(?<=\\{)(?<sepSpace>${escapedSep}? )?["]`, "g"), `$<sepSpace>${LEFT_DOUBLE_QUOTE}`);
     const endingDouble = `(?<beforeQuote>[^\\s\\(])["]((?<sepAfter>${escapedSep})?)(?=${escapedSep}|[\\s/\\).,;${EM_DASH}:\\-\\}!?s]|$)`;
@@ -87,7 +89,7 @@ function convertDoubleQuotes(text, sep) {
 }
 /** Apply American or British punctuation style */
 function applyPunctuationStyle(text, sep, style) {
-    const escapedSep = escapeStringRegexp(sep);
+    const escapedSep = getEscapedSeparator({ separator: sep });
     if (style === "american") {
         // Period outside → inside: "Hello". → "Hello."
         const periodOutsideRegex = cachedRegExp(`(?<![${TERMINAL_PUNCTUATION_CLASS}])(?<sepBefore>${escapedSep}?)(?<quote>[${RIGHT_SINGLE_QUOTE}${RIGHT_DOUBLE_QUOTE}])(?<sepAfter>${escapedSep}?)(?!\\.\\.\\.)\\.`, "g");
@@ -99,11 +101,13 @@ function applyPunctuationStyle(text, sep, style) {
     else if (style === "british" || style === "german" || style === "french") {
         // Period inside → outside: "Hello." → "Hello".
         // No terminal punctuation guard — "Stop!." inside is always wrong; move the period out.
-        const periodInsideRegex = cachedRegExp(`(?<sepBefore>${escapedSep}?)\\.(?<sepMiddle>${escapedSep}?)(?<quote>[${RIGHT_SINGLE_QUOTE}${RIGHT_DOUBLE_QUOTE}])`, "g");
-        text = text.replace(periodInsideRegex, "$<sepBefore>$<sepMiddle>$<quote>.");
+        // Match ALL consecutive closing quotes so nested quotes like .'" become '". in one pass.
+        const periodInsideRegex = cachedRegExp(`(?<sepBefore>${escapedSep}?)\\.(?<quotes>(?:${escapedSep}?[${RIGHT_SINGLE_QUOTE}${RIGHT_DOUBLE_QUOTE}])+)`, "g");
+        text = text.replace(periodInsideRegex, "$<sepBefore>$<quotes>.");
         // Comma inside → outside: "Hello," → "Hello",
-        const commaInsideRegex = cachedRegExp(`,(?<sepAndQuote>${escapedSep}?[${RIGHT_DOUBLE_QUOTE}${RIGHT_SINGLE_QUOTE}])`, "g");
-        text = text.replace(commaInsideRegex, "$<sepAndQuote>,");
+        // Match ALL consecutive closing quotes so nested quotes like ,'" become '", in one pass.
+        const commaInsideRegex = cachedRegExp(`,(?<quotes>(?:${escapedSep}?[${RIGHT_DOUBLE_QUOTE}${RIGHT_SINGLE_QUOTE}])+)`, "g");
+        text = text.replace(commaInsideRegex, "$<quotes>,");
     }
     return text;
 }
@@ -135,6 +139,16 @@ function normalizeGermanQuotes(text) {
             result += RIGHT_SINGLE_QUOTE;
             singleDepth--;
         }
+        else if (ch === RIGHT_DOUBLE_QUOTE) {
+            // RDQ is not used in German typography — normalize to straight quote
+            // so the pipeline can re-classify it (e.g., from a previous American pass)
+            result += '"';
+        }
+        else if (ch === RIGHT_SINGLE_QUOTE) {
+            // RSQ is not used in German typography — normalize to straight quote
+            // so the pipeline can re-classify apostrophes vs closing quotes
+            result += "'";
+        }
         else {
             result += ch;
         }

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package/dist/utils.d.ts.map

@@ -1 +1 @@
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+{"version":3,"file":"utils.d.ts","sourceRoot":"","sources":["../src/utils.ts"],"names":[],"mappings":"AAAA;;;;GAIG;AAOH;;;;;;GAMG;AACH,wBAAgB,iBAAiB,CAAC,OAAO,EAAE,MAAM,EAAE,KAAK,EAAE,MAAM,GAAG,MAAM,CAkBxE;AAED;;;;;;;GAOG;AACH,wBAAgB,qBAAqB,CAAC,UAAU,EAAE,MAAM,EAAE,EAAE,SAAS,EAAE,MAAM,GAAG,IAAI,CAanF;AAED,wBAAgB,eAAe,CAAC,IAAI,EAAE,MAAM,EAAE,SAAS,GAAE,MAA0B,GAAG,MAAM,CAQ3F;AAED;;;;;;;;;GASG;AACH,wBAAgB,6BAA6B,CAC3C,QAAQ,EAAE,MAAM,EAChB,WAAW,EAAE,MAAM,EACnB,SAAS,GAAE,MAA0B,EACrC,aAAa,GAAE,MAAoB,GAClC,IAAI,CAUN"}

package/dist/utils.js

@@ -41,17 +41,20 @@ export function assertSeparatorAbsent(textValues, separator) {
     for (const value of textValues) {
         if (!value.includes(separator))
             continue;
-        const codePoint = `U+${separator.codePointAt(0).toString(16).toUpperCase().padStart(4, "0")}`;
-        throw new Error(`Text contains the separator character ${codePoint} which is used internally by punctilio ` +
-            `to track element boundaries. Pass a different character via the "separator" option.\n` +
+        const codePoints = [...separator]
+            .map(ch => `U+${ch.codePointAt(0).toString(16).toUpperCase().padStart(4, "0")}`)
+            .join(" ");
+        throw new Error(`Text contains the separator sequence ${codePoints} which is used internally by punctilio ` +
+            `to track element boundaries. Pass a different separator via the "separator" option.\n` +
             `Text: ${formatErrorString(value, "input")}`);
     }
 }
 export function countSeparators(text, separator = DEFAULT_SEPARATOR) {
     let count = 0;
-    for (const char of text) {
-        if (char === separator)
-            count++;
+    let index = 0;
+    while ((index = text.indexOf(separator, index)) !== -1) {
+        count++;
+        index += separator.length;
     }
     return count;
 }

package/dist/utils.js.map

@@ -1 +1 @@
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+{"version":3,"file":"utils.js","sourceRoot":"","sources":["../src/utils.ts"],"names":[],"mappings":"AAAA;;;;GAIG;AAEH,OAAO,EAAE,iBAAiB,EAAE,MAAM,gBAAgB,CAAA;AAElD,qEAAqE;AACrE,MAAM,sBAAsB,GAAG,IAAI,CAAA;AAEnC;;;;;;GAMG;AACH,MAAM,UAAU,iBAAiB,CAAC,OAAe,EAAE,KAAa;IAC9D,IAAI,OAAO,CAAC,MAAM,IAAI,sBAAsB,EAAE,CAAC;QAC7C,OAAO,IAAI,CAAC,SAAS,CAAC,OAAO,CAAC,CAAA;IAChC,CAAC;IAED,yDAAyD;IACzD,IAAI,CAAC;QACH,IAAI,OAAO,UAAU,CAAC,OAAO,EAAE,MAAM,EAAE,KAAK,KAAK,UAAU,EAAE,CAAC;YAC5D,UAAU,CAAC,OAAO,CAAC,MAAM,CAAC,KAAK,CAC7B,gBAAgB,KAAK,kBAAkB,OAAO,CAAC,MAAM,cAAc,OAAO,MAAM,CACjF,CAAA;QACH,CAAC;IACH,CAAC;IAAC,MAAM,CAAC;QACP,gDAAgD;IAClD,CAAC;IAED,MAAM,SAAS,GAAG,OAAO,CAAC,KAAK,CAAC,CAAC,EAAE,sBAAsB,CAAC,CAAA;IAC1D,OAAO,IAAI,KAAK,KAAK,IAAI,CAAC,SAAS,CAAC,SAAS,CAAC,QAAQ,OAAO,CAAC,MAAM,gBAAgB,CAAA;AACtF,CAAC;AAED;;;;;;;GAOG;AACH,MAAM,UAAU,qBAAqB,CAAC,UAAoB,EAAE,SAAiB;IAC3E,KAAK,MAAM,KAAK,IAAI,UAAU,EAAE,CAAC;QAC/B,IAAI,CAAC,KAAK,CAAC,QAAQ,CAAC,SAAS,CAAC;YAAE,SAAQ;QAExC,MAAM,UAAU,GAAG,CAAC,GAAG,SAAS,CAAC;aAC9B,GAAG,CAAC,EAAE,CAAC,EAAE,CAAC,KAAK,EAAE,CAAC,WAAW,CAAC,CAAC,CAAE,CAAC,QAAQ,CAAC,EAAE,CAAC,CAAC,WAAW,EAAE,CAAC,QAAQ,CAAC,CAAC,EAAE,GAAG,CAAC,EAAE,CAAC;aAChF,IAAI,CAAC,GAAG,CAAC,CAAA;QACZ,MAAM,IAAI,KAAK,CACb,wCAAwC,UAAU,yCAAyC;YAC3F,uFAAuF;YACvF,SAAS,iBAAiB,CAAC,KAAK,EAAE,OAAO,CAAC,EAAE,CAC7C,CAAA;IACH,CAAC;AACH,CAAC;AAED,MAAM,UAAU,eAAe,CAAC,IAAY,EAAE,YAAoB,iBAAiB;IACjF,IAAI,KAAK,GAAG,CAAC,CAAA;IACb,IAAI,KAAK,GAAG,CAAC,CAAA;IACb,OAAO,CAAC,KAAK,GAAG,IAAI,CAAC,OAAO,CAAC,SAAS,EAAE,KAAK,CAAC,CAAC,KAAK,CAAC,CAAC,EAAE,CAAC;QACvD,KAAK,EAAE,CAAA;QACP,KAAK,IAAI,SAAS,CAAC,MAAM,CAAA;IAC3B,CAAC;IACD,OAAO,KAAK,CAAA;AACd,CAAC;AAED;;;;;;;;;GASG;AACH,MAAM,UAAU,6BAA6B,CAC3C,QAAgB,EAChB,WAAmB,EACnB,YAAoB,iBAAiB,EACrC,gBAAwB,WAAW;IAEnC,MAAM,aAAa,GAAG,eAAe,CAAC,QAAQ,EAAE,SAAS,CAAC,CAAA;IAC1D,MAAM,gBAAgB,GAAG,eAAe,CAAC,WAAW,EAAE,SAAS,CAAC,CAAA;IAChE,IAAI,aAAa,KAAK,gBAAgB,EAAE,CAAC;QACvC,MAAM,IAAI,KAAK,CACb,GAAG,aAAa,sCAAsC,aAAa,SAAS,gBAAgB,KAAK;YACjG,4GAA4G;YAC5G,gDAAgD,CACjD,CAAA;IACH,CAAC;AACH,CAAC"}

package/package.json

@@ -1,6 +1,6 @@
 {
   "name": "punctilio",
-  "version": "3.1.0",
+  "version": "3.1.2",
   "description": "Smart typography transformations: curly quotes, em-dashes, en-dashes, and more",
   "type": "module",
   "main": "./dist/index.js",

package/src/constants.ts

@@ -122,23 +122,28 @@ export const TERMINAL_PUNCTUATION = [
 export const LATIN_LETTERS = "A-Za-z\\u00C0-\\u00D6\\u00D8-\\u00F6\\u00F8-\\u00FF\\u0100-\\u017F\\u0180-\\u024F"
 
 /**
- * Default separator character for text spanning HTML elements.
- * Uses Unicode Private Use Area character U+E000.
+ * Default separator for text spanning HTML elements.
+ * Uses a two-character sentinel from the Unicode Private Use Area
+ * (U+E000 U+E001) to avoid collisions with CJK fonts, Apple emoji
+ * internals, PDF-to-text output, and icon fonts that repurpose U+E000.
  */
-export const DEFAULT_SEPARATOR = "\uE000"
+export const DEFAULT_SEPARATOR = "\uE000\uE001"
 export const ESCAPED_DEFAULT_SEPARATOR = escapeStringRegexp(DEFAULT_SEPARATOR)
 
 /**
- * Returns the regex-escaped separator string for the given options.
- * Centralizes the common pattern of falling back to the pre-escaped default.
+ * Returns the regex-escaped separator string for the given options,
+ * wrapped in a non-capturing group so that quantifiers like `?` and `*`
+ * apply to the entire separator sequence (critical for multi-character
+ * separators like the default U+E000 U+E001).
  *
  * @param options - Object with an optional `separator` field
- * @returns Regex-escaped separator string
+ * @returns Regex-escaped separator string wrapped in `(?:...)`
  */
 export function getEscapedSeparator(options: { separator?: string }): string {
-  return options.separator
+  const escaped = options.separator
     ? escapeStringRegexp(options.separator)
     : ESCAPED_DEFAULT_SEPARATOR
+  return `(?:${escaped})`
 }
 
 /**
@@ -197,22 +202,28 @@ export const SPACE_CHARS = ` ${UNICODE_SYMBOLS.NBSP}`
  * Creates a lookbehind pattern that matches after whitespace, separator, or start of string.
  * Used for arrow patterns and other constructs that should appear at word boundaries.
  *
- * @param escapedSeparator - Regex-escaped separator string
- * @returns Pattern string: `(?<=[\\s${sep}]|^)`
+ * Uses alternation instead of a character class so that multi-character
+ * separators are matched as a sequence, not as individual characters.
+ *
+ * @param escapedSeparator - Regex-escaped separator string (may be grouped)
+ * @returns Pattern string: `(?<=\\s|${sep}|^)`
  */
 export function spaceBoundaryStart(escapedSeparator: string): string {
-  return `(?<=[\\s${escapedSeparator}]|^)`
+  return `(?<=\\s|${escapedSeparator}|^)`
 }
 
 /**
  * Creates a lookahead pattern that matches before whitespace, separator, or end of string.
  * Used for arrow patterns and other constructs that should appear at word boundaries.
  *
- * @param escapedSeparator - Regex-escaped separator string
- * @returns Pattern string: `(?=[\\s${sep}]|$)`
+ * Uses alternation instead of a character class so that multi-character
+ * separators are matched as a sequence, not as individual characters.
+ *
+ * @param escapedSeparator - Regex-escaped separator string (may be grouped)
+ * @returns Pattern string: `(?=\\s|${sep}|$)`
  */
 export function spaceBoundaryEnd(escapedSeparator: string): string {
-  return `(?=[\\s${escapedSeparator}]|$)`
+  return `(?=\\s|${escapedSeparator}|$)`
 }
 
 /**

package/src/dashes.ts

@@ -2,7 +2,6 @@
  * Dash transformation: hyphens → em-dashes, en-dashes, minus signs.
  */
 
-import escapeStringRegexp from "escape-string-regexp"
 import { UNICODE_SYMBOLS, DEFAULT_SEPARATOR, LATIN_LETTERS, wordBoundaryStart, wordBoundaryEnd, getEscapedSeparator, cachedRegExp } from "./constants.js"
 
 export type DashStyle = "american" | "british" | "none"
@@ -150,7 +149,7 @@ export function minusReplace(text: string, options: DashOptions = {}): string {
 function convertParentheticalDashes(text: string, sep: string, style: DashStyle): string {
   const localizedDash = style === "british" ? EN_DASH : EM_DASH
   const maybeSpace = style === "british" ? " " : ""
-  const escapedSep = escapeStringRegexp(sep)
+  const escapedSep = getEscapedSeparator({ separator: sep })
 
   // Convert spaced dashes: "word - word" or "word — word"
   // When a separator follows the dash, preserve trailing spaces (they belong to the next text segment).
@@ -198,7 +197,7 @@ function convertParentheticalDashes(text: string, sep: string, style: DashStyle)
  * allows a space after the dash: "Don't inter— Hey! Who threw that?"
  */
 function normalizeEmDashSpacing(text: string, sep: string): string {
-  const escapedSep = escapeStringRegexp(sep)
+  const escapedSep = getEscapedSeparator({ separator: sep })
 
   // Remove all spaces around em-dashes
   text = text.replace(

package/src/index.ts

@@ -222,14 +222,19 @@ const defaultOpts: Required<Omit<TransformOptions, "separator">> = {
 export function transform(text: string, options: TransformOptions = {}): string {
   const separator = options.separator ?? DEFAULT_SEPARATOR
 
-  // Validate separator: must be a single UTF-16 code unit (BMP character)
-  // Multi-codepoint characters (surrogate pairs like emoji) cause issues with regex patterns
-  if (separator.length !== 1) {
-    throw new Error(
-      `Invalid separator: must be a single character. ` +
-      `Received "${separator}" (length: ${separator.length}). ` +
-      `Use a single-codepoint character like the default "\\uE000".`
-    )
+  // Validate separator: must be non-empty and contain only BMP characters.
+  // for...of iterates by code point; surrogate pairs (non-BMP) yield a
+  // two-UTF16-unit string, so ch.length > 1 detects them.
+  if (separator.length === 0) {
+    throw new Error("Invalid separator: must not be empty.")
+  }
+  for (const ch of separator) {
+    if (ch.length > 1) {
+      throw new Error(
+        `Invalid separator: must contain only BMP characters (no characters outside the Basic Multilingual Plane). ` +
+        `Received "${separator}" which contains a non-BMP character.`
+      )
+    }
   }
 
   const original = text

package/src/nbsp.ts

@@ -135,8 +135,9 @@ export function nbspBetweenNumberAndUnit(text: string, options: NbspOptions = {}
  */
 export function nbspBeforeLastWord(text: string, options: NbspOptions = {}): string {
   const sep = getEscapedSeparator(options)
+  // Use alternation instead of character classes for multi-char separator support
   const pattern = cachedRegExp(
-    `(?<=[\\w${sep}])${SPACE}(?<lastWord>[^\\s${sep}]{1,10})(?<ending>${sep}?(?:\\n\\n|$))`,
+    `(?<=\\w|${sep})${SPACE}(?<lastWord>(?:(?!\\s)(?!${sep}).){1,10})(?<ending>${sep}?(?:\\n\\n|$))`,
     "g"
   )
   return text.replace(pattern, `${NBSP}$<lastWord>$<ending>`)

package/src/quotes.ts

@@ -3,7 +3,7 @@
  */
 
 import escapeStringRegexp from "escape-string-regexp"
-import { UNICODE_SYMBOLS, DEFAULT_SEPARATOR, LATIN_LETTERS, TERMINAL_PUNCTUATION, cachedRegExp } from "./constants.js"
+import { UNICODE_SYMBOLS, DEFAULT_SEPARATOR, LATIN_LETTERS, TERMINAL_PUNCTUATION, getEscapedSeparator, cachedRegExp } from "./constants.js"
 
 const {
   EM_DASH,
@@ -28,7 +28,7 @@ export interface QuoteOptions {
 
 /** Convert straight single quotes to curly quotes and apostrophes */
 function convertSingleQuotes(text: string, sep: string): string {
-  const escapedSep = escapeStringRegexp(sep)
+  const escapedSep = getEscapedSeparator({ separator: sep })
 
   // Handle empty single quotes '' and whitespace-only quotes ' ' first
   // Only match straight quotes, not already-converted curly quotes
@@ -96,7 +96,9 @@ function convertUnmatchedPluralPossessives(text: string, sep: string): string {
         return match
       }
       let i = offset - 1
-      while (i >= 0 && text[i] === sep) i--
+      while (i >= sep.length - 1 && text.startsWith(sep, i - sep.length + 1)) {
+        i -= sep.length
+      }
       if (i >= 0 && (text[i] === "s" || text[i] === "S")) {
         return MODIFIER_LETTER_APOSTROPHE
       }
@@ -107,7 +109,8 @@ function convertUnmatchedPluralPossessives(text: string, sep: string): string {
 
 /** Convert straight double quotes to curly quotes */
 function convertDoubleQuotes(text: string, sep: string): string {
-  const escapedSep = escapeStringRegexp(sep)
+  const rawEscSep = escapeStringRegexp(sep)
+  const escapedSep = getEscapedSeparator({ separator: sep })
 
   // Handle empty quotes "" first - match only when not part of adjacent quotes
   // Require word boundary or start/end of string on at least one side
@@ -116,7 +119,7 @@ function convertDoubleQuotes(text: string, sep: string): string {
   text = text.replace(/(?<=^|[\s([{])"(?<whitespace>\s+)"(?=$|[\s)\]}.!?,;:])/g, `${LEFT_DOUBLE_QUOTE}$<whitespace>${RIGHT_DOUBLE_QUOTE}`)
 
   const beginningDouble = cachedRegExp(
-    `(?<=^|[\\s\\(\\/\\[\\{\\-${EM_DASH}${escapedSep}])(?<beforeChr>${escapedSep}?)["](?<afterChr>(?<sepWithPunct>${escapedSep}[ .,])|(?=${escapedSep}?\\.{3}|${escapedSep}?[^\\s\\)\\${EM_DASH},!?${escapedSep};:.\\}]))`,
+    `(?<=^|[\\s\\(\\/\\[\\{\\-${EM_DASH}]|${escapedSep})(?<beforeChr>${escapedSep}?)["](?<afterChr>(?<sepWithPunct>${escapedSep}[ .,])|(?=${escapedSep}?\\.{3}|${escapedSep}?[^\\s\\)${EM_DASH},!?;:.\\}${rawEscSep}]))`,
     "gm"
   )
   text = text.replace(beginningDouble, `$<beforeChr>${LEFT_DOUBLE_QUOTE}$<afterChr>`)
@@ -134,7 +137,7 @@ function convertDoubleQuotes(text: string, sep: string): string {
 
 /** Apply American or British punctuation style */
 function applyPunctuationStyle(text: string, sep: string, style: PunctuationStyle): string {
-  const escapedSep = escapeStringRegexp(sep)
+  const escapedSep = getEscapedSeparator({ separator: sep })
 
   if (style === "american") {
     // Period outside → inside: "Hello". → "Hello."
@@ -153,18 +156,20 @@ function applyPunctuationStyle(text: string, sep: string, style: PunctuationStyl
   } else if (style === "british" || style === "german" || style === "french") {
     // Period inside → outside: "Hello." → "Hello".
     // No terminal punctuation guard — "Stop!." inside is always wrong; move the period out.
+    // Match ALL consecutive closing quotes so nested quotes like .'" become '". in one pass.
     const periodInsideRegex = cachedRegExp(
-      `(?<sepBefore>${escapedSep}?)\\.(?<sepMiddle>${escapedSep}?)(?<quote>[${RIGHT_SINGLE_QUOTE}${RIGHT_DOUBLE_QUOTE}])`,
+      `(?<sepBefore>${escapedSep}?)\\.(?<quotes>(?:${escapedSep}?[${RIGHT_SINGLE_QUOTE}${RIGHT_DOUBLE_QUOTE}])+)`,
       "g"
     )
-    text = text.replace(periodInsideRegex, "$<sepBefore>$<sepMiddle>$<quote>.")
+    text = text.replace(periodInsideRegex, "$<sepBefore>$<quotes>.")
 
     // Comma inside → outside: "Hello," → "Hello",
+    // Match ALL consecutive closing quotes so nested quotes like ,'" become '", in one pass.
     const commaInsideRegex = cachedRegExp(
-      `,(?<sepAndQuote>${escapedSep}?[${RIGHT_DOUBLE_QUOTE}${RIGHT_SINGLE_QUOTE}])`,
+      `,(?<quotes>(?:${escapedSep}?[${RIGHT_DOUBLE_QUOTE}${RIGHT_SINGLE_QUOTE}])+)`,
       "g"
     )
-    text = text.replace(commaInsideRegex, "$<sepAndQuote>,")
+    text = text.replace(commaInsideRegex, "$<quotes>,")
   }
   return text
 }
@@ -195,6 +200,14 @@ function normalizeGermanQuotes(text: string): string {
     } else if (ch === LEFT_SINGLE_QUOTE && singleDepth > 0) {
       result += RIGHT_SINGLE_QUOTE
       singleDepth--
+    } else if (ch === RIGHT_DOUBLE_QUOTE) {
+      // RDQ is not used in German typography — normalize to straight quote
+      // so the pipeline can re-classify it (e.g., from a previous American pass)
+      result += '"'
+    } else if (ch === RIGHT_SINGLE_QUOTE) {
+      // RSQ is not used in German typography — normalize to straight quote
+      // so the pipeline can re-classify apostrophes vs closing quotes
+      result += "'"
     } else {
       result += ch
     }

package/src/tests/index.test.ts

@@ -443,6 +443,19 @@ describe("transform", () => {
       expect(second).toBe(first)
     })
 
+    it.each([
+      // Nested quotes with period — tests the multi-quote-jump fix
+      [`"She said, 'Hello.'"`, "british" as const],
+      [`"She said, 'Hello.'"`, "german" as const],
+      [`"She said, 'Hello.'"`, "french" as const],
+      // Leading apostrophe — tests the German RSQ normalization fix
+      [`'Twas the night before Christmas.`, "german" as const],
+    ])('is idempotent across styles: "%s" [%s]', (input, style) => {
+      const first = transform(input, { punctuationStyle: style })
+      const second = transform(first, { punctuationStyle: style })
+      expect(second).toBe(first)
+    })
+
     it.each([
       `${LEFT_DOUBLE_QUOTE}Hello${RIGHT_DOUBLE_QUOTE}`,
       `word${EM_DASH}word`,
@@ -558,18 +571,17 @@ describe("transform", () => {
 
   describe("separator validation", () => {
     const invalidSeparators = [
-      ["🎉", "emoji (multi-codepoint)"],
-      ["ab", "multi-character"],
+      ["🎉", "emoji (non-BMP)"],
       ["", "empty string"],
     ] as const
 
     it.each(invalidSeparators)("rejects %s separator (%s)", (sep) => {
       expect(() => transform('"Hello"', { separator: sep, nbsp: false })).toThrow(
-        /Invalid separator.*must be a single character/
+        /Invalid separator/
       )
     })
 
-    const validSeparators = ["\uE000", "|", "\u2603"] // Default, pipe, snowman
+    const validSeparators = ["\uE000\uE001", "\uE000", "|", "\u2603", "ab"] // Default, single PUA, pipe, snowman, multi-char
 
     it.each(validSeparators)("accepts '%s' as separator", (sep) => {
       expect(() => transform('"Hello"', { separator: sep, nbsp: false })).not.toThrow()
@@ -584,6 +596,25 @@ describe("transform", () => {
     })
   })
 
+  describe("multi-character separator behavior", () => {
+    const sep = "\uE000\uE001"
+
+    it.each([
+      ["quotes with separator at boundary", `${sep}"Hello"`, `${sep}${LEFT_DOUBLE_QUOTE}Hello${RIGHT_DOUBLE_QUOTE}`],
+      ["em-dash with adjacent separators", `word${sep} - ${sep}word`, `word${sep}${EM_DASH}${sep}word`],
+      ["ellipsis with separator between dots", `a.${sep}.${sep}.`, `a\u2026${sep}${sep}`],
+      ["nbsp before last word with trailing separator", `Hello world${sep}`, `Hello${NBSP}world${sep}`],
+    ])("%s", (_desc, input, expected) => {
+      expect(transform(input, { separator: sep, nbsp: true })).toBe(expected)
+    })
+
+    it("preserves separator count through transform", () => {
+      const input = `${sep}"Hello"${sep} -- ${sep}world${sep}`
+      const result = transform(input, { separator: sep })
+      expect(countSeparators(result, sep)).toBe(countSeparators(input, sep))
+    })
+  })
+
   describe("Unicode preservation", () => {
     it.each([
       ["emoji", '"Hello 👋 World"', `${LEFT_DOUBLE_QUOTE}Hello 👋 World${RIGHT_DOUBLE_QUOTE}`],

package/src/tests/quotes.test.ts

@@ -653,6 +653,8 @@ describe("niceQuotes", () => {
       [`"She said 'hello'"`, `${DOUBLE_LOW_9_QUOTE}She said ${SINGLE_LOW_9_QUOTE}hello${LEFT_SINGLE_QUOTE}${LEFT_DOUBLE_QUOTE}`, { punctuationStyle: "german" as const }],
       // French punctuation placement
       ['"Bonjour," dit-il.', `${LEFT_GUILLEMET}${NBSP}Bonjour${NBSP}${RIGHT_GUILLEMET}, dit-il.`, { punctuationStyle: "french" as const }],
+      // German leading apostrophe ('Twas)
+      ["'Twas the night", `${RIGHT_SINGLE_QUOTE}Twas the night`, { punctuationStyle: "german" as const }],
     ])("locale quotes: %s → %s", (input, expected, options) => {
       it("transforms correctly", () => {
         expect(niceQuotes(input, options)).toBe(expected)
@@ -663,9 +665,39 @@ describe("niceQuotes", () => {
       [`${DOUBLE_LOW_9_QUOTE}Guten Tag${LEFT_DOUBLE_QUOTE}`, { punctuationStyle: "german" as const }],
       [`${SINGLE_LOW_9_QUOTE}Hallo${LEFT_SINGLE_QUOTE}`, { punctuationStyle: "german" as const }],
       [`${LEFT_GUILLEMET}${NBSP}Bonjour${NBSP}${RIGHT_GUILLEMET}`, { punctuationStyle: "french" as const }],
+      // German apostrophe idempotency — RSQ must not flip to LSQ on re-processing
+      [`${RIGHT_SINGLE_QUOTE}Twas the night`, { punctuationStyle: "german" as const }],
     ])("locale output is idempotent: %s", (input, options) => {
       expect(niceQuotes(input, options)).toBe(input)
     })
+
+    it("german normalizer re-classifies pre-existing RDQ", () => {
+      // RDQ is not used in German — should become German closing double
+      const input = `${LEFT_DOUBLE_QUOTE}Hello${RIGHT_DOUBLE_QUOTE}`
+      expect(niceQuotes(input, { punctuationStyle: "german" })).toBe(`${DOUBLE_LOW_9_QUOTE}Hello${LEFT_DOUBLE_QUOTE}`)
+    })
+  })
+
+  describe("nested quote punctuation placement", () => {
+    it.each([
+      // Period moves past all closing quotes in one pass
+      [
+        `${LEFT_DOUBLE_QUOTE}He said, ${LEFT_SINGLE_QUOTE}Hello.${RIGHT_SINGLE_QUOTE}${RIGHT_DOUBLE_QUOTE}`,
+        `${LEFT_DOUBLE_QUOTE}He said, ${LEFT_SINGLE_QUOTE}Hello${RIGHT_SINGLE_QUOTE}${RIGHT_DOUBLE_QUOTE}.`,
+      ],
+      // Comma moves past all closing quotes in one pass
+      [
+        `${LEFT_DOUBLE_QUOTE}He said, ${LEFT_SINGLE_QUOTE}Hello,${RIGHT_SINGLE_QUOTE}${RIGHT_DOUBLE_QUOTE} she replied.`,
+        `${LEFT_DOUBLE_QUOTE}He said, ${LEFT_SINGLE_QUOTE}Hello${RIGHT_SINGLE_QUOTE}${RIGHT_DOUBLE_QUOTE}, she replied.`,
+      ],
+    ])("british moves past all closing quotes: %s → %s", (input, expected) => {
+      expect(niceQuotes(input, { punctuationStyle: "british" })).toBe(expected)
+    })
+
+    it.each(["british", "german", "french"] as const)("%s nested quote period is idempotent", (style) => {
+      const first = niceQuotes(`"He said, 'Hello.'"`, { punctuationStyle: style })
+      expect(niceQuotes(first, { punctuationStyle: style })).toBe(first)
+    })
   })
 
   describe("pathological inputs", () => {

package/src/tests/utils.test.ts

@@ -10,9 +10,9 @@ describe("assertSeparatorAbsent", () => {
   })
 
   it.each([
-    ["default separator", [`hello${DEFAULT_SEPARATOR}world`], DEFAULT_SEPARATOR, /U\+E000/],
+    ["default separator", [`hello${DEFAULT_SEPARATOR}world`], DEFAULT_SEPARATOR, /U\+E000 U\+E001/],
     ["custom separator", ["hello|world"], "|", /U\+007C/],
-    ["separator in middle element", ["clean", `has${DEFAULT_SEPARATOR}sep`, "also clean"], DEFAULT_SEPARATOR, /separator character/],
+    ["separator in middle element", ["clean", `has${DEFAULT_SEPARATOR}sep`, "also clean"], DEFAULT_SEPARATOR, /separator sequence/],
   ])("throws: %s", (_desc, values, separator, expectedPattern) => {
     expect(() => assertSeparatorAbsent(values, separator)).toThrow(expectedPattern)
   })

package/src/utils.ts

@@ -48,10 +48,12 @@ export function assertSeparatorAbsent(textValues: string[], separator: string):
   for (const value of textValues) {
     if (!value.includes(separator)) continue
 
-    const codePoint = `U+${separator.codePointAt(0)!.toString(16).toUpperCase().padStart(4, "0")}`
+    const codePoints = [...separator]
+      .map(ch => `U+${ch.codePointAt(0)!.toString(16).toUpperCase().padStart(4, "0")}`)
+      .join(" ")
     throw new Error(
-      `Text contains the separator character ${codePoint} which is used internally by punctilio ` +
-      `to track element boundaries. Pass a different character via the "separator" option.\n` +
+      `Text contains the separator sequence ${codePoints} which is used internally by punctilio ` +
+      `to track element boundaries. Pass a different separator via the "separator" option.\n` +
       `Text: ${formatErrorString(value, "input")}`
     )
   }
@@ -59,8 +61,10 @@ export function assertSeparatorAbsent(textValues: string[], separator: string):
 
 export function countSeparators(text: string, separator: string = DEFAULT_SEPARATOR): number {
   let count = 0
-  for (const char of text) {
-    if (char === separator) count++
+  let index = 0
+  while ((index = text.indexOf(separator, index)) !== -1) {
+    count++
+    index += separator.length
   }
   return count
 }