punctilio 2.1.1 → 2.2.0

package/README.md

@@ -149,3 +149,4 @@ transform(text, {
   - Spaced en-dashes between words (word – word)
 - Setting either style to `none` skips the entire transform category: `punctuationStyle: 'none'` preserves straight quotes, apostrophes, and prime marks; `dashStyle: 'none'` preserves all hyphens, number ranges, date ranges, and minus signs.
 - `punctilio` is idempotent by design: `transform(transform(text))` always equals `transform(text)`. If performance is critical, set `checkIdempotency: false` to skip the verification pass.
+- When `useModifierLetterApostrophe` is enabled, apostrophes use Modifier Letter Apostrophe (U+02BC) while closing single quotes use Right Single Quotation Mark (U+2019), producing semantically distinct codepoints in most cases. Contractions (don't), possessives (dog's), and leading abbreviations ('twas, '99) all output U+02BC. Bare trailing possessives like `dogs'` remain ambiguous. This option is off by default since U+02BC may not be matched by downstream regex patterns that expect standard quote characters.

package/dist/constants.d.ts

@@ -49,6 +49,7 @@ export declare const UNICODE_SYMBOLS: {
     readonly RIGHT_DOUBLE_QUOTE: "”";
     readonly LEFT_SINGLE_QUOTE: "‘";
     readonly RIGHT_SINGLE_QUOTE: "’";
+    readonly MODIFIER_LETTER_APOSTROPHE: "ʼ";
     readonly NBSP: " ";
     readonly SUPERSCRIPT_ST: "ˢᵗ";
     readonly SUPERSCRIPT_ND: "ⁿᵈ";

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;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;CAmDlB,CAAA;AAEV;;;;;;;;;;;GAWG;AACH,eAAO,MAAM,aAAa,sFAAsF,CAAA;AAEhH;;;GAGG;AACH,eAAO,MAAM,iBAAiB,WAAW,CAAA;AACzC,eAAO,MAAM,yBAAyB,QAAwC,CAAA;AAE9E;;;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;;;;;;GAMG;AACH,wBAAgB,kBAAkB,CAAC,gBAAgB,EAAE,MAAM,GAAG,MAAM,CAEnE;AAED;;;;;;GAMG;AACH,wBAAgB,gBAAgB,CAAC,gBAAgB,EAAE,MAAM,GAAG,MAAM,CAEjE"}

package/dist/constants.js

@@ -50,6 +50,7 @@ export const UNICODE_SYMBOLS = {
     RIGHT_DOUBLE_QUOTE: "\u201D",
     LEFT_SINGLE_QUOTE: "\u2018",
     RIGHT_SINGLE_QUOTE: "\u2019",
+    MODIFIER_LETTER_APOSTROPHE: "\u02BC",
     NBSP: "\u00A0",
     // Superscript ordinal suffixes
     SUPERSCRIPT_ST: "\u02E2\u1D57", // ˢᵗ

package/dist/constants.js.map

@@ -1 +1 @@
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+{"version":3,"file":"constants.js","sourceRoot":"","sources":["../src/constants.ts"],"names":[],"mappings":"AAAA;;;;;;;;GAQG;AAEH,OAAO,kBAAkB,MAAM,sBAAsB,CAAA;AAErD;;GAEG;AACH,MAAM,CAAC,MAAM,eAAe,GAAG;IAC7B,QAAQ,EAAE,QAAQ;IAClB,cAAc,EAAE,QAAQ;IACxB,SAAS,EAAE,QAAQ;IACnB,UAAU,EAAE,QAAQ;IACpB,SAAS,EAAE,QAAQ;IACnB,UAAU,EAAE,QAAQ;IACpB,SAAS,EAAE,QAAQ;IACnB,MAAM,EAAE,QAAQ;IAChB,WAAW,EAAE,QAAQ;IACrB,UAAU,EAAE,QAAQ;IACpB,gBAAgB,EAAE,QAAQ;IAC1B,WAAW,EAAE,QAAQ;IACrB,UAAU,EAAE,QAAQ;IACpB,aAAa,EAAE,QAAQ;IACvB,KAAK,EAAE,QAAQ;IACf,YAAY,EAAE,QAAQ;IACtB,YAAY,EAAE,QAAQ;IACtB,YAAY,EAAE,QAAQ;IACtB,YAAY,EAAE,QAAQ;IACtB,YAAY,EAAE,QAAQ;IACtB,YAAY,EAAE,QAAQ;IACtB,YAAY,EAAE,QAAQ;IACtB,YAAY,EAAE,QAAQ;IACtB,YAAY,EAAE,QAAQ;IACtB,YAAY,EAAE,QAAQ;IACtB,YAAY,EAAE,QAAQ;IACtB,YAAY,EAAE,QAAQ;IACtB,YAAY,EAAE,QAAQ;IACtB,YAAY,EAAE,QAAQ;IACtB,YAAY,EAAE,QAAQ;IACtB,YAAY,EAAE,QAAQ;IACtB,OAAO,EAAE,QAAQ;IACjB,OAAO,EAAE,QAAQ;IACjB,KAAK,EAAE,QAAQ;IACf,iBAAiB,EAAE,QAAQ;IAC3B,kBAAkB,EAAE,QAAQ;IAC5B,iBAAiB,EAAE,QAAQ;IAC3B,kBAAkB,EAAE,QAAQ;IAC5B,0BAA0B,EAAE,QAAQ;IACpC,IAAI,EAAE,QAAQ;IACd,+BAA+B;IAC/B,cAAc,EAAE,cAAc,EAAE,KAAK;IACrC,cAAc,EAAE,cAAc,EAAE,KAAK;IACrC,cAAc,EAAE,cAAc,EAAE,KAAK;IACrC,cAAc,EAAE,cAAc,EAAE,KAAK;IACrC,wBAAwB;IACxB,eAAe,EAAE,QAAQ,EAAE,IAAI;IAC/B,oBAAoB,EAAE,QAAQ,EAAE,IAAI;IACpC,oBAAoB,EAAE,QAAQ,EAAE,IAAI;IACpC,kBAAkB,EAAE,QAAQ,EAAE,IAAI;CAC1B,CAAA;AAEV;;;;;;;;;;;GAWG;AACH,MAAM,CAAC,MAAM,aAAa,GAAG,mFAAmF,CAAA;AAEhH;;;GAGG;AACH,MAAM,CAAC,MAAM,iBAAiB,GAAG,QAAQ,CAAA;AACzC,MAAM,CAAC,MAAM,yBAAyB,GAAG,kBAAkB,CAAC,iBAAiB,CAAC,CAAA;AAE9E;;;GAGG;AACH,MAAM,CAAC,MAAM,mBAAmB,GAAG,CAAC,GAAG,EAAE,GAAG,EAAE,GAAG,EAAE,GAAG,EAAE,GAAG,EAAE,GAAG,EAAE,GAAG,EAAE,GAAG,EAAE,IAAI,EAAE,GAAG,EAAE,GAAG,EAAE,GAAG,CAAU,CAAA;AAEzG;;;;;;;;;;;;;;;GAeG;AACH,MAAM,UAAU,iBAAiB,CAAC,gBAAwB;IACxD,OAAO,UAAU,gBAAgB,OAAO,CAAA;AAC1C,CAAC;AAED;;;;;;;;;;;;;;;GAeG;AACH,MAAM,UAAU,eAAe,CAAC,gBAAwB;IACtD,OAAO,SAAS,gBAAgB,OAAO,CAAA;AACzC,CAAC;AAED;;;GAGG;AACH,MAAM,CAAC,MAAM,WAAW,GAAG,IAAI,eAAe,CAAC,IAAI,EAAE,CAAA;AAErD;;;;;;GAMG;AACH,MAAM,UAAU,kBAAkB,CAAC,gBAAwB;IACzD,OAAO,WAAW,gBAAgB,MAAM,CAAA;AAC1C,CAAC;AAED;;;;;;GAMG;AACH,MAAM,UAAU,gBAAgB,CAAC,gBAAwB;IACvD,OAAO,UAAU,gBAAgB,MAAM,CAAA;AACzC,CAAC"}

package/dist/dashes.js

@@ -148,11 +148,11 @@ export function hyphenReplace(text, options = {}) {
     if (style === "none")
         return text;
     text = minusReplace(text, options);
+    text = enDashDateRange(text, options);
     text = convertParentheticalDashes(text, sep, style);
     if (style === "american")
         text = normalizeEmDashSpacing(text, sep);
     text = enDashNumberRange(text, options);
-    text = enDashDateRange(text, options);
     return text;
 }
 //# sourceMappingURL=dashes.js.map

package/dist/dashes.js.map

@@ -1 +1 @@
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package/dist/index.d.ts

@@ -105,8 +105,20 @@ export interface TransformOptions {
      * Default: true
      */
     checkIdempotency?: boolean;
+    /**
+     * Use modifier letter apostrophe (U+02BC) instead of right single quote
+     * (U+2019) for contractions and possessives. This distinguishes apostrophes
+     * from closing quotes in most cases, though some ambiguous patterns (e.g.,
+     * `dogs'` vs a closing single quote) cannot be resolved without semantic
+     * understanding. May also break downstream regex patterns that expect
+     * standard quote characters like /don\u2019t/ or /O\u2019Brien/.
+     *
+     * Default: false
+     */
+    useModifierLetterApostrophe?: boolean;
 }
 export { assertSeparatorCountPreserved, countSeparators } from "./utils.js";
-export { DEFAULT_SEPARATOR } from "./constants.js";
+export { DEFAULT_SEPARATOR, UNICODE_SYMBOLS } from "./constants.js";
+export declare const MODIFIER_LETTER_APOSTROPHE: "ʼ";
 export declare function transform(text: string, options?: TransformOptions): string;
 //# sourceMappingURL=index.d.ts.map

package/dist/index.d.ts.map

@@ -1 +1 @@
-{"version":3,"file":"index.d.ts","sourceRoot":"","sources":["../src/index.ts"],"names":[],"mappings":"AAAA;;;;;;;;GAQG;AAEH,OAAO,EAAE,UAAU,EAAE,KAAK,YAAY,EAAE,KAAK,gBAAgB,EAAE,MAAM,aAAa,CAAA;AAClF,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;;;;;;;;;;;;;OAaG;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;CAC3B;AASD,OAAO,EAAE,6BAA6B,EAAE,eAAe,EAAE,MAAM,YAAY,CAAA;AAC3E,OAAO,EAAE,iBAAiB,EAAE,MAAM,gBAAgB,CAAA;AAiDlD,wBAAgB,SAAS,CAAC,IAAI,EAAE,MAAM,EAAE,OAAO,GAAE,gBAAqB,GAAG,MAAM,CAmE9E"}
+{"version":3,"file":"index.d.ts","sourceRoot":"","sources":["../src/index.ts"],"names":[],"mappings":"AAAA;;;;;;;;GAQG;AAEH,OAAO,EAAE,UAAU,EAAE,KAAK,YAAY,EAAE,KAAK,gBAAgB,EAAE,MAAM,aAAa,CAAA;AAClF,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;;;;;;;;;;;;;OAaG;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;IAE1B;;;;;;;;;OASG;IACH,2BAA2B,CAAC,EAAE,OAAO,CAAA;CACtC;AASD,OAAO,EAAE,6BAA6B,EAAE,eAAe,EAAE,MAAM,YAAY,CAAA;AAC3E,OAAO,EAAE,iBAAiB,EAAE,eAAe,EAAE,MAAM,gBAAgB,CAAA;AACnE,eAAO,MAAM,0BAA0B,KAA6C,CAAA;AAkDpF,wBAAgB,SAAS,CAAC,IAAI,EAAE,MAAM,EAAE,OAAO,GAAE,gBAAqB,GAAG,MAAM,CA8E9E"}

package/dist/index.js

@@ -16,9 +16,10 @@ import { hyphenReplace } from "./dashes.js";
 import { symbolTransform, fractions as fractionsTransform, degrees as degreesTransform, superscriptOrdinal as superscriptTransform, primeMarks, collapseSpaces as collapseSpacesTransform, punctuationLigatures as ligaturesTransform } from "./symbols.js";
 import { nbspTransform as nbspTransformFn } from "./nbsp.js";
 import { assertSeparatorCountPreserved, formatErrorString } from "./utils.js";
-import { DEFAULT_SEPARATOR } from "./constants.js";
+import { DEFAULT_SEPARATOR, UNICODE_SYMBOLS } from "./constants.js";
 export { assertSeparatorCountPreserved, countSeparators } from "./utils.js";
-export { DEFAULT_SEPARATOR } from "./constants.js";
+export { DEFAULT_SEPARATOR, UNICODE_SYMBOLS } from "./constants.js";
+export const MODIFIER_LETTER_APOSTROPHE = UNICODE_SYMBOLS.MODIFIER_LETTER_APOSTROPHE;
 /**
  * Applies all typography transformations: smart quotes, proper dashes,
  * and symbol improvements.
@@ -64,6 +65,7 @@ const defaultOpts = {
     checkIdempotency: true,
     punctuationStyle: "american",
     dashStyle: "american",
+    useModifierLetterApostrophe: false,
 };
 export function transform(text, options = {}) {
     const separator = options.separator ?? DEFAULT_SEPARATOR;
@@ -75,12 +77,17 @@ export function transform(text, options = {}) {
             `Use a single-codepoint character like the default "\\uE000".`);
     }
     const original = text;
-    const { symbols, fractions, degrees, superscript, ligatures, nbsp, collapseSpaces, checkIdempotency, ...separatorOpts } = { ...defaultOpts, ...options };
+    const { symbols, fractions, degrees, superscript, ligatures, nbsp, collapseSpaces, checkIdempotency, useModifierLetterApostrophe, ...separatorOpts } = { ...defaultOpts, ...options };
     text = hyphenReplace(text, separatorOpts);
     if (separatorOpts.punctuationStyle !== "none") {
         text = primeMarks(text, separatorOpts);
     }
-    text = niceQuotes(text, separatorOpts);
+    // niceQuotes must output MLA here regardless of the user's option,
+    // because NBSP's PUNCTUATION_OR_QUOTE class includes RSQ but not MLA.
+    // Without this, apostrophes in "don't" would act as word boundaries
+    // during NBSP insertion. The final MLA→RSQ conversion at line 286
+    // runs after all transforms complete.
+    text = niceQuotes(text, { ...separatorOpts, useModifierLetterApostrophe: true });
     if (symbols) {
         text = symbolTransform(text, separatorOpts);
     }
@@ -103,6 +110,11 @@ export function transform(text, options = {}) {
         text = nbspTransformFn(text, separatorOpts);
     }
     assertSeparatorCountPreserved(original, text, separator, "transform");
+    // Convert MLA→RSQ for regex-friendly output, after all transforms
+    // (especially NBSP which relies on MLA being letter-like).
+    if (!useModifierLetterApostrophe) {
+        text = text.replaceAll(UNICODE_SYMBOLS.MODIFIER_LETTER_APOSTROPHE, UNICODE_SYMBOLS.RIGHT_SINGLE_QUOTE);
+    }
     if (checkIdempotency) {
         const secondPass = transform(text, { ...options, checkIdempotency: false });
         /* istanbul ignore if -- defensive check that should never trigger */

package/dist/index.js.map

@@ -1 +1 @@
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+{"version":3,"file":"index.js","sourceRoot":"","sources":["../src/index.ts"],"names":[],"mappings":"AAAA;;;;;;;;GAQG;AAEH,OAAO,EAAE,UAAU,EAA4C,MAAM,aAAa,CAAA;AAElF,OAAO,EACL,aAAa,EACb,iBAAiB,EACjB,eAAe,EACf,YAAY,EACZ,MAAM,EACN,6BAA6B,GAG9B,MAAM,aAAa,CAAA;AAEpB,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,GAEhB,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,GAExB,MAAM,WAAW,CAAA;AAsHlB,OAAO,EAAE,UAAU,EAAE,MAAM,aAAa,CAAA;AACxC,OAAO,EAAE,aAAa,EAAE,MAAM,aAAa,CAAA;AAC3C,OAAO,EAAE,eAAe,EAAE,SAAS,IAAI,kBAAkB,EAAE,OAAO,IAAI,gBAAgB,EAAE,kBAAkB,IAAI,oBAAoB,EAAE,UAAU,EAAE,cAAc,IAAI,uBAAuB,EAAE,oBAAoB,IAAI,kBAAkB,EAAE,MAAM,cAAc,CAAA;AAC3P,OAAO,EAAE,aAAa,IAAI,eAAe,EAAE,MAAM,WAAW,CAAA;AAC5D,OAAO,EAAE,6BAA6B,EAAE,iBAAiB,EAAE,MAAM,YAAY,CAAA;AAC7E,OAAO,EAAE,iBAAiB,EAAE,eAAe,EAAE,MAAM,gBAAgB,CAAA;AAEnE,OAAO,EAAE,6BAA6B,EAAE,eAAe,EAAE,MAAM,YAAY,CAAA;AAC3E,OAAO,EAAE,iBAAiB,EAAE,eAAe,EAAE,MAAM,gBAAgB,CAAA;AACnE,MAAM,CAAC,MAAM,0BAA0B,GAAG,eAAe,CAAC,0BAA0B,CAAA;AAEpF;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;GAiCG;AACH,MAAM,WAAW,GAAkD;IACjE,OAAO,EAAE,IAAI;IACb,SAAS,EAAE,KAAK;IAChB,OAAO,EAAE,KAAK;IACd,WAAW,EAAE,KAAK;IAClB,SAAS,EAAE,KAAK;IAChB,IAAI,EAAE,IAAI;IACV,cAAc,EAAE,IAAI;IACpB,gBAAgB,EAAE,IAAI;IACtB,gBAAgB,EAAE,UAAU;IAC5B,SAAS,EAAE,UAAU;IACrB,2BAA2B,EAAE,KAAK;CACnC,CAAA;AAED,MAAM,UAAU,SAAS,CAAC,IAAY,EAAE,UAA4B,EAAE;IACpE,MAAM,SAAS,GAAG,OAAO,CAAC,SAAS,IAAI,iBAAiB,CAAA;IAExD,wEAAwE;IACxE,2FAA2F;IAC3F,IAAI,SAAS,CAAC,MAAM,KAAK,CAAC,EAAE,CAAC;QAC3B,MAAM,IAAI,KAAK,CACb,iDAAiD;YACjD,aAAa,SAAS,cAAc,SAAS,CAAC,MAAM,KAAK;YACzD,8DAA8D,CAC/D,CAAA;IACH,CAAC;IAED,MAAM,QAAQ,GAAG,IAAI,CAAA;IACrB,MAAM,EAAE,OAAO,EAAE,SAAS,EAAE,OAAO,EAAE,WAAW,EAAE,SAAS,EAAE,IAAI,EAAE,cAAc,EAAE,gBAAgB,EAAE,2BAA2B,EAAE,GAAG,aAAa,EAAE,GAAG,EAAE,GAAG,WAAW,EAAE,GAAG,OAAO,EAAE,CAAA;IAErL,IAAI,GAAG,aAAa,CAAC,IAAI,EAAE,aAAa,CAAC,CAAA;IACzC,IAAI,aAAa,CAAC,gBAAgB,KAAK,MAAM,EAAE,CAAC;QAC9C,IAAI,GAAG,UAAU,CAAC,IAAI,EAAE,aAAa,CAAC,CAAA;IACxC,CAAC;IACD,mEAAmE;IACnE,sEAAsE;IACtE,oEAAoE;IACpE,kEAAkE;IAClE,sCAAsC;IACtC,IAAI,GAAG,UAAU,CAAC,IAAI,EAAE,EAAE,GAAG,aAAa,EAAE,2BAA2B,EAAE,IAAI,EAAE,CAAC,CAAA;IAEhF,IAAI,OAAO,EAAE,CAAC;QACZ,IAAI,GAAG,eAAe,CAAC,IAAI,EAAE,aAAa,CAAC,CAAA;IAC7C,CAAC;IAED,IAAI,SAAS,EAAE,CAAC;QACd,IAAI,GAAG,kBAAkB,CAAC,IAAI,CAAC,CAAA;IACjC,CAAC;IAED,IAAI,OAAO,EAAE,CAAC;QACZ,IAAI,GAAG,gBAAgB,CAAC,IAAI,CAAC,CAAA;IAC/B,CAAC;IAED,IAAI,WAAW,EAAE,CAAC;QAChB,IAAI,GAAG,oBAAoB,CAAC,IAAI,EAAE,aAAa,CAAC,CAAA;IAClD,CAAC;IAED,IAAI,SAAS,EAAE,CAAC;QACd,IAAI,GAAG,kBAAkB,CAAC,IAAI,EAAE,aAAa,CAAC,CAAA;IAChD,CAAC;IAED,IAAI,cAAc,EAAE,CAAC;QACnB,IAAI,GAAG,uBAAuB,CAAC,IAAI,CAAC,CAAA;IACtC,CAAC;IAED,IAAI,IAAI,EAAE,CAAC;QACT,IAAI,GAAG,eAAe,CAAC,IAAI,EAAE,aAAa,CAAC,CAAA;IAC7C,CAAC;IAED,6BAA6B,CAAC,QAAQ,EAAE,IAAI,EAAE,SAAS,EAAE,WAAW,CAAC,CAAA;IAErE,kEAAkE;IAClE,2DAA2D;IAC3D,IAAI,CAAC,2BAA2B,EAAE,CAAC;QACjC,IAAI,GAAG,IAAI,CAAC,UAAU,CAAC,eAAe,CAAC,0BAA0B,EAAE,eAAe,CAAC,kBAAkB,CAAC,CAAA;IACxG,CAAC;IAED,IAAI,gBAAgB,EAAE,CAAC;QACrB,MAAM,UAAU,GAAG,SAAS,CAAC,IAAI,EAAE,EAAE,GAAG,OAAO,EAAE,gBAAgB,EAAE,KAAK,EAAE,CAAC,CAAA;QAC3E,qEAAqE;QACrE,IAAI,IAAI,KAAK,UAAU,EAAE,CAAC;YACxB,MAAM,IAAI,KAAK,CACb,gCAAgC;gBAChC,gBAAgB,iBAAiB,CAAC,IAAI,EAAE,YAAY,CAAC,IAAI;gBACzD,gBAAgB,iBAAiB,CAAC,UAAU,EAAE,aAAa,CAAC,IAAI;gBAChE,4GAA4G;gBAC5G,gDAAgD,CACjD,CAAA;QACH,CAAC;IACH,CAAC;IAED,OAAO,IAAI,CAAA;AACb,CAAC"}

package/dist/quotes.d.ts

@@ -7,6 +7,17 @@ export interface QuoteOptions {
     separator?: string;
     /** "american" (inside), "british" (outside), "none". Default: "american" */
     punctuationStyle?: PunctuationStyle;
+    /**
+     * Use modifier letter apostrophe (U+02BC) instead of right single quote
+     * (U+2019) for contractions and possessives. This distinguishes apostrophes
+     * from closing quotes in most cases, though some ambiguous patterns (e.g.,
+     * `dogs'` vs a closing single quote) cannot be resolved without semantic
+     * understanding. May also break downstream regex patterns that expect
+     * standard quote characters like /don\u2019t/ or /O\u2019Brien/.
+     *
+     * Default: false
+     */
+    useModifierLetterApostrophe?: boolean;
 }
 /** Convert straight quotes to smart quotes. */
 export declare function niceQuotes(text: string, options?: QuoteOptions): string;

package/dist/quotes.d.ts.map

@@ -1 +1 @@
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+{"version":3,"file":"quotes.d.ts","sourceRoot":"","sources":["../src/quotes.ts"],"names":[],"mappings":"AAAA;;GAEG;AAeH,MAAM,MAAM,gBAAgB,GAAG,UAAU,GAAG,SAAS,GAAG,MAAM,CAAA;AAE9D,MAAM,WAAW,YAAY;IAC3B,qEAAqE;IACrE,SAAS,CAAC,EAAE,MAAM,CAAA;IAClB,4EAA4E;IAC5E,gBAAgB,CAAC,EAAE,gBAAgB,CAAA;IACnC;;;;;;;;;OASG;IACH,2BAA2B,CAAC,EAAE,OAAO,CAAA;CACtC;AAiHD,+CAA+C;AAC/C,wBAAgB,UAAU,CAAC,IAAI,EAAE,MAAM,EAAE,OAAO,GAAE,YAAiB,GAAG,MAAM,CAiB3E"}

package/dist/quotes.js

@@ -3,26 +3,38 @@
  */
 import escapeStringRegexp from "escape-string-regexp";
 import { UNICODE_SYMBOLS, DEFAULT_SEPARATOR, LATIN_LETTERS } from "./constants.js";
-const { EM_DASH, LEFT_DOUBLE_QUOTE, RIGHT_DOUBLE_QUOTE, LEFT_SINGLE_QUOTE, RIGHT_SINGLE_QUOTE, ELLIPSIS, } = UNICODE_SYMBOLS;
+const { EM_DASH, LEFT_DOUBLE_QUOTE, RIGHT_DOUBLE_QUOTE, LEFT_SINGLE_QUOTE, RIGHT_SINGLE_QUOTE, MODIFIER_LETTER_APOSTROPHE, ELLIPSIS, } = UNICODE_SYMBOLS;
 /** Convert straight single quotes to curly quotes and apostrophes */
 function convertSingleQuotes(text, sep) {
     const escapedSep = escapeStringRegexp(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}`;
+    const singleQuoteChars = `'${LEFT_SINGLE_QUOTE}${RIGHT_SINGLE_QUOTE}${MODIFIER_LETTER_APOSTROPHE}`;
     text = text.replace(new RegExp(`(?<![${singleQuoteChars}])''(?![${singleQuoteChars}])`, "g"), `${LEFT_SINGLE_QUOTE}${RIGHT_SINGLE_QUOTE}`);
     text = text.replace(new RegExp(`(?<![${singleQuoteChars}])'(\\s+)'(?![${singleQuoteChars}])`, "g"), `${LEFT_SINGLE_QUOTE}$1${RIGHT_SINGLE_QUOTE}`);
     const afterEndingSinglePatterns = `\\s\\.!?;,\\)${EM_DASH}\\-\\]"`;
+    // Full pattern with optional 's' for lookahead detection in apostropheRegex
     const afterEndingSingle = `(?=${escapedSep}?(?:s${escapedSep}?)?(?:[${afterEndingSinglePatterns}]|$))`;
-    const endingSingle = `(?<=[^\\s${LEFT_DOUBLE_QUOTE}'])[']${afterEndingSingle}`;
-    text = text.replace(new RegExp(endingSingle, "gm"), RIGHT_SINGLE_QUOTE);
-    const contraction = `(?<=[${LATIN_LETTERS}])['${RIGHT_SINGLE_QUOTE}](?=${escapedSep}?[${LATIN_LETTERS}])`;
-    text = text.replace(new RegExp(contraction, "gm"), RIGHT_SINGLE_QUOTE);
-    const apostropheWhitelist = `(?=n${RIGHT_SINGLE_QUOTE} )`;
-    const endQuoteNotContraction = `(?!${contraction})${RIGHT_SINGLE_QUOTE}${afterEndingSingle}`;
+    // Handle 'n' abbreviation (Rock 'n' Roll). Before MLA this wasn't needed —
+    // the general rules produced LSQ+n+RSQ which was fine. But MLA requires both
+    // quotes to be MLA (semantic apostrophes), and the general rules can't achieve
+    // that: neither quote is in a contraction context (no Latin letter on both sides).
+    text = text.replace(new RegExp(`(?<=\\w${escapedSep}? )[']n['](?= ${escapedSep}?\\w)`, "gm"), `${MODIFIER_LETTER_APOSTROPHE}n${MODIFIER_LETTER_APOSTROPHE}`);
+    // Possessive: 's followed by ending context (e.g., dog's) → U+02BC
+    const afterPossessive = `(?=${escapedSep}?s${escapedSep}?(?:[${afterEndingSinglePatterns}]|$))`;
+    const possessiveSingle = `(?<=[^\\s${LEFT_DOUBLE_QUOTE}'])[']${afterPossessive}`;
+    text = text.replace(new RegExp(possessiveSingle, "gm"), MODIFIER_LETTER_APOSTROPHE);
+    // Closing single quote: ending context without 's' → U+2019
+    const afterClosingSingle = `(?=${escapedSep}?(?:[${afterEndingSinglePatterns}]|$))`;
+    const closingSingle = `(?<=[^\\s${LEFT_DOUBLE_QUOTE}'])[']${afterClosingSingle}`;
+    text = text.replace(new RegExp(closingSingle, "gm"), RIGHT_SINGLE_QUOTE);
+    const contraction = `(?<=[${LATIN_LETTERS}])['${RIGHT_SINGLE_QUOTE}${MODIFIER_LETTER_APOSTROPHE}](?=${escapedSep}?[${LATIN_LETTERS}])`;
+    text = text.replace(new RegExp(contraction, "gm"), MODIFIER_LETTER_APOSTROPHE);
+    const apostropheWhitelist = `(?=n${MODIFIER_LETTER_APOSTROPHE} )`;
+    const endQuoteNotContraction = `(?!${contraction})[${RIGHT_SINGLE_QUOTE}${MODIFIER_LETTER_APOSTROPHE}]${afterEndingSingle}`;
     // Limit lookahead scan to 1000 chars to prevent catastrophic backtracking on pathological inputs
     const apostropheRegex = new RegExp(`(?<=^|[^\\w])'(${apostropheWhitelist}|(?![^${LEFT_SINGLE_QUOTE}'\\n]{0,1000}${endQuoteNotContraction}))`, "gm");
-    text = text.replace(apostropheRegex, RIGHT_SINGLE_QUOTE);
+    text = text.replace(apostropheRegex, MODIFIER_LETTER_APOSTROPHE);
     const beginningSingle = `(?<beforeContext>(?:^|[\\s${LEFT_DOUBLE_QUOTE}${RIGHT_DOUBLE_QUOTE}${EM_DASH}\\-\\(])${escapedSep}?)['](?=${escapedSep}?\\S)`;
     text = text.replace(new RegExp(beginningSingle, "gm"), `$<beforeContext>${LEFT_SINGLE_QUOTE}`);
     return text;
@@ -74,6 +86,12 @@ export function niceQuotes(text, options = {}) {
     text = convertSingleQuotes(text, sep);
     text = convertDoubleQuotes(text, sep);
     text = applyPunctuationStyle(text, sep, punctuationStyle);
+    // MLA is used internally so applyPunctuationStyle can distinguish
+    // apostrophes (MLA, don't move) from closing quotes (RSQ, do move).
+    // Convert back to RSQ unless the caller opts into the distinction.
+    if (!options.useModifierLetterApostrophe) {
+        text = text.replaceAll(MODIFIER_LETTER_APOSTROPHE, RIGHT_SINGLE_QUOTE);
+    }
     return text;
 }
 //# sourceMappingURL=quotes.js.map

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package/package.json

@@ -1,6 +1,6 @@
 {
   "name": "punctilio",
-  "version": "2.1.1",
+  "version": "2.2.0",
   "description": "Smart typography transformations: curly quotes, em-dashes, en-dashes, and more",
   "type": "module",
   "main": "./dist/index.js",

package/src/constants.ts

@@ -52,6 +52,7 @@ export const UNICODE_SYMBOLS = {
   RIGHT_DOUBLE_QUOTE: "\u201D",
   LEFT_SINGLE_QUOTE: "\u2018",
   RIGHT_SINGLE_QUOTE: "\u2019",
+  MODIFIER_LETTER_APOSTROPHE: "\u02BC",
   NBSP: "\u00A0",
   // Superscript ordinal suffixes
   SUPERSCRIPT_ST: "\u02E2\u1D57", // ˢᵗ

package/src/dashes.ts

@@ -218,9 +218,9 @@ export function hyphenReplace(text: string, options: DashOptions = {}): string {
   const style = options.dashStyle ?? "american"
   if (style === "none") return text
   text = minusReplace(text, options)
+  text = enDashDateRange(text, options)
   text = convertParentheticalDashes(text, sep, style)
   if (style === "american") text = normalizeEmDashSpacing(text, sep)
   text = enDashNumberRange(text, options)
-  text = enDashDateRange(text, options)
   return text
 }

package/src/index.ts

@@ -154,6 +154,18 @@ export interface TransformOptions {
    * Default: true
    */
   checkIdempotency?: boolean
+
+  /**
+   * Use modifier letter apostrophe (U+02BC) instead of right single quote
+   * (U+2019) for contractions and possessives. This distinguishes apostrophes
+   * from closing quotes in most cases, though some ambiguous patterns (e.g.,
+   * `dogs'` vs a closing single quote) cannot be resolved without semantic
+   * understanding. May also break downstream regex patterns that expect
+   * standard quote characters like /don\u2019t/ or /O\u2019Brien/.
+   *
+   * Default: false
+   */
+  useModifierLetterApostrophe?: boolean
 }
 
 import { niceQuotes } from "./quotes.js"
@@ -161,10 +173,11 @@ import { hyphenReplace } from "./dashes.js"
 import { symbolTransform, fractions as fractionsTransform, degrees as degreesTransform, superscriptOrdinal as superscriptTransform, primeMarks, collapseSpaces as collapseSpacesTransform, punctuationLigatures as ligaturesTransform } from "./symbols.js"
 import { nbspTransform as nbspTransformFn } from "./nbsp.js"
 import { assertSeparatorCountPreserved, formatErrorString } from "./utils.js"
-import { DEFAULT_SEPARATOR } from "./constants.js"
+import { DEFAULT_SEPARATOR, UNICODE_SYMBOLS } from "./constants.js"
 
 export { assertSeparatorCountPreserved, countSeparators } from "./utils.js"
-export { DEFAULT_SEPARATOR } from "./constants.js"
+export { DEFAULT_SEPARATOR, UNICODE_SYMBOLS } from "./constants.js"
+export const MODIFIER_LETTER_APOSTROPHE = UNICODE_SYMBOLS.MODIFIER_LETTER_APOSTROPHE
 
 /**
  * Applies all typography transformations: smart quotes, proper dashes,
@@ -211,6 +224,7 @@ const defaultOpts: Required<Omit<TransformOptions, "separator">> = {
   checkIdempotency: true,
   punctuationStyle: "american",
   dashStyle: "american",
+  useModifierLetterApostrophe: false,
 }
 
 export function transform(text: string, options: TransformOptions = {}): string {
@@ -227,13 +241,18 @@ export function transform(text: string, options: TransformOptions = {}): string
   }
 
   const original = text
-  const { symbols, fractions, degrees, superscript, ligatures, nbsp, collapseSpaces, checkIdempotency, ...separatorOpts } = { ...defaultOpts, ...options }
+  const { symbols, fractions, degrees, superscript, ligatures, nbsp, collapseSpaces, checkIdempotency, useModifierLetterApostrophe, ...separatorOpts } = { ...defaultOpts, ...options }
 
   text = hyphenReplace(text, separatorOpts)
   if (separatorOpts.punctuationStyle !== "none") {
     text = primeMarks(text, separatorOpts)
   }
-  text = niceQuotes(text, separatorOpts)
+  // niceQuotes must output MLA here regardless of the user's option,
+  // because NBSP's PUNCTUATION_OR_QUOTE class includes RSQ but not MLA.
+  // Without this, apostrophes in "don't" would act as word boundaries
+  // during NBSP insertion. The final MLA→RSQ conversion at line 286
+  // runs after all transforms complete.
+  text = niceQuotes(text, { ...separatorOpts, useModifierLetterApostrophe: true })
 
   if (symbols) {
     text = symbolTransform(text, separatorOpts)
@@ -265,6 +284,12 @@ export function transform(text: string, options: TransformOptions = {}): string
 
   assertSeparatorCountPreserved(original, text, separator, "transform")
 
+  // Convert MLA→RSQ for regex-friendly output, after all transforms
+  // (especially NBSP which relies on MLA being letter-like).
+  if (!useModifierLetterApostrophe) {
+    text = text.replaceAll(UNICODE_SYMBOLS.MODIFIER_LETTER_APOSTROPHE, UNICODE_SYMBOLS.RIGHT_SINGLE_QUOTE)
+  }
+
   if (checkIdempotency) {
     const secondPass = transform(text, { ...options, checkIdempotency: false })
     /* istanbul ignore if -- defensive check that should never trigger */

package/src/quotes.ts

@@ -11,6 +11,7 @@ const {
   RIGHT_DOUBLE_QUOTE,
   LEFT_SINGLE_QUOTE,
   RIGHT_SINGLE_QUOTE,
+  MODIFIER_LETTER_APOSTROPHE,
   ELLIPSIS,
 } = UNICODE_SYMBOLS
 
@@ -21,6 +22,17 @@ export interface QuoteOptions {
   separator?: string
   /** "american" (inside), "british" (outside), "none". Default: "american" */
   punctuationStyle?: PunctuationStyle
+  /**
+   * Use modifier letter apostrophe (U+02BC) instead of right single quote
+   * (U+2019) for contractions and possessives. This distinguishes apostrophes
+   * from closing quotes in most cases, though some ambiguous patterns (e.g.,
+   * `dogs'` vs a closing single quote) cannot be resolved without semantic
+   * understanding. May also break downstream regex patterns that expect
+   * standard quote characters like /don\u2019t/ or /O\u2019Brien/.
+   *
+   * Default: false
+   */
+  useModifierLetterApostrophe?: boolean
 }
 
 /** Convert straight single quotes to curly quotes and apostrophes */
@@ -29,26 +41,41 @@ function convertSingleQuotes(text: string, sep: string): string {
 
   // 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}`
+  const singleQuoteChars = `'${LEFT_SINGLE_QUOTE}${RIGHT_SINGLE_QUOTE}${MODIFIER_LETTER_APOSTROPHE}`
   text = text.replace(new RegExp(`(?<![${singleQuoteChars}])''(?![${singleQuoteChars}])`, "g"), `${LEFT_SINGLE_QUOTE}${RIGHT_SINGLE_QUOTE}`)
   text = text.replace(new RegExp(`(?<![${singleQuoteChars}])'(\\s+)'(?![${singleQuoteChars}])`, "g"), `${LEFT_SINGLE_QUOTE}$1${RIGHT_SINGLE_QUOTE}`)
 
   const afterEndingSinglePatterns = `\\s\\.!?;,\\)${EM_DASH}\\-\\]"`
+  // Full pattern with optional 's' for lookahead detection in apostropheRegex
   const afterEndingSingle = `(?=${escapedSep}?(?:s${escapedSep}?)?(?:[${afterEndingSinglePatterns}]|$))`
-  const endingSingle = `(?<=[^\\s${LEFT_DOUBLE_QUOTE}'])[']${afterEndingSingle}`
-  text = text.replace(new RegExp(endingSingle, "gm"), RIGHT_SINGLE_QUOTE)
 
-  const contraction = `(?<=[${LATIN_LETTERS}])['${RIGHT_SINGLE_QUOTE}](?=${escapedSep}?[${LATIN_LETTERS}])`
-  text = text.replace(new RegExp(contraction, "gm"), RIGHT_SINGLE_QUOTE)
+  // Handle 'n' abbreviation (Rock 'n' Roll). Before MLA this wasn't needed —
+  // the general rules produced LSQ+n+RSQ which was fine. But MLA requires both
+  // quotes to be MLA (semantic apostrophes), and the general rules can't achieve
+  // that: neither quote is in a contraction context (no Latin letter on both sides).
+  text = text.replace(new RegExp(`(?<=\\w${escapedSep}? )[']n['](?= ${escapedSep}?\\w)`, "gm"), `${MODIFIER_LETTER_APOSTROPHE}n${MODIFIER_LETTER_APOSTROPHE}`)
 
-  const apostropheWhitelist = `(?=n${RIGHT_SINGLE_QUOTE} )`
-  const endQuoteNotContraction = `(?!${contraction})${RIGHT_SINGLE_QUOTE}${afterEndingSingle}`
+  // Possessive: 's followed by ending context (e.g., dog's) → U+02BC
+  const afterPossessive = `(?=${escapedSep}?s${escapedSep}?(?:[${afterEndingSinglePatterns}]|$))`
+  const possessiveSingle = `(?<=[^\\s${LEFT_DOUBLE_QUOTE}'])[']${afterPossessive}`
+  text = text.replace(new RegExp(possessiveSingle, "gm"), MODIFIER_LETTER_APOSTROPHE)
+
+  // Closing single quote: ending context without 's' → U+2019
+  const afterClosingSingle = `(?=${escapedSep}?(?:[${afterEndingSinglePatterns}]|$))`
+  const closingSingle = `(?<=[^\\s${LEFT_DOUBLE_QUOTE}'])[']${afterClosingSingle}`
+  text = text.replace(new RegExp(closingSingle, "gm"), RIGHT_SINGLE_QUOTE)
+
+  const contraction = `(?<=[${LATIN_LETTERS}])['${RIGHT_SINGLE_QUOTE}${MODIFIER_LETTER_APOSTROPHE}](?=${escapedSep}?[${LATIN_LETTERS}])`
+  text = text.replace(new RegExp(contraction, "gm"), MODIFIER_LETTER_APOSTROPHE)
+
+  const apostropheWhitelist = `(?=n${MODIFIER_LETTER_APOSTROPHE} )`
+  const endQuoteNotContraction = `(?!${contraction})[${RIGHT_SINGLE_QUOTE}${MODIFIER_LETTER_APOSTROPHE}]${afterEndingSingle}`
   // Limit lookahead scan to 1000 chars to prevent catastrophic backtracking on pathological inputs
   const apostropheRegex = new RegExp(
     `(?<=^|[^\\w])'(${apostropheWhitelist}|(?![^${LEFT_SINGLE_QUOTE}'\\n]{0,1000}${endQuoteNotContraction}))`,
     "gm"
   )
-  text = text.replace(apostropheRegex, RIGHT_SINGLE_QUOTE)
+  text = text.replace(apostropheRegex, MODIFIER_LETTER_APOSTROPHE)
 
   const beginningSingle = `(?<beforeContext>(?:^|[\\s${LEFT_DOUBLE_QUOTE}${RIGHT_DOUBLE_QUOTE}${EM_DASH}\\-\\(])${escapedSep}?)['](?=${escapedSep}?\\S)`
   text = text.replace(new RegExp(beginningSingle, "gm"), `$<beforeContext>${LEFT_SINGLE_QUOTE}`)
@@ -129,5 +156,12 @@ export function niceQuotes(text: string, options: QuoteOptions = {}): string {
   text = convertDoubleQuotes(text, sep)
   text = applyPunctuationStyle(text, sep, punctuationStyle)
 
+  // MLA is used internally so applyPunctuationStyle can distinguish
+  // apostrophes (MLA, don't move) from closing quotes (RSQ, do move).
+  // Convert back to RSQ unless the caller opts into the distinction.
+  if (!options.useModifierLetterApostrophe) {
+    text = text.replaceAll(MODIFIER_LETTER_APOSTROPHE, RIGHT_SINGLE_QUOTE)
+  }
+
   return text
 }

package/src/tests/dashes.test.ts

@@ -111,6 +111,19 @@ describe("hyphenReplace", () => {
     })
   })
 
+  describe("month ranges to en dashes", () => {
+    it.each([
+      ["Jan-Mar", `Jan${EN_DASH}Mar`],
+      ["Mar - Nov", `Mar${EN_DASH}Nov`],
+      ["January - March", `January${EN_DASH}March`],
+      ["October 2012 - December 2014", `October 2012${EN_DASH}December 2014`],
+      ["Jan 2000 - Feb", `Jan 2000${EN_DASH}Feb`],
+      ["March - April 2025", `March${EN_DASH}April 2025`],
+    ])('converts "%s"', (input, expected) => {
+      expect(hyphenReplace(input)).toBe(expected)
+    })
+  })
+
   describe("with separator character", () => {
     const sep = "\uE000"
     it.each([

package/src/tests/index.test.ts

@@ -233,6 +233,7 @@ describe("transform", () => {
       expect(transform(input, { nbsp: false })).toBe(expected)
     })
 
+
     it("handles measurement text", () => {
       const input = 'He is 6\'2" tall.'
       const expected = `He is 6${PRIME}2${DOUBLE_PRIME} tall.`

package/src/tests/quotes.test.ts

@@ -1,15 +1,19 @@
 import { niceQuotes } from "../quotes.js"
-import { UNICODE_SYMBOLS } from "../constants.js"
+import { UNICODE_SYMBOLS, DEFAULT_SEPARATOR } from "../constants.js"
 
 const {
   LEFT_DOUBLE_QUOTE,
   RIGHT_DOUBLE_QUOTE,
   LEFT_SINGLE_QUOTE,
   RIGHT_SINGLE_QUOTE,
+  MODIFIER_LETTER_APOSTROPHE,
   EM_DASH,
   ELLIPSIS,
 } = UNICODE_SYMBOLS
 
+/** Enable MLA output for tests that assert the apostrophe codepoint. */
+const MLA = { useModifierLetterApostrophe: true } as const
+
 describe("niceQuotes", () => {
   describe("double quotes", () => {
     it.each([
@@ -27,14 +31,14 @@ describe("niceQuotes", () => {
       ],
       ['"world model";', `${LEFT_DOUBLE_QUOTE}world model${RIGHT_DOUBLE_QUOTE};`],
       ['"party"/"wedding."', `${LEFT_DOUBLE_QUOTE}party${RIGHT_DOUBLE_QUOTE}/${LEFT_DOUBLE_QUOTE}wedding.${RIGHT_DOUBLE_QUOTE}`],
-      ['"Hi \'Trout!"', `${LEFT_DOUBLE_QUOTE}Hi ${RIGHT_SINGLE_QUOTE}Trout!${RIGHT_DOUBLE_QUOTE}`],
+      ['"Hi \'Trout!"', `${LEFT_DOUBLE_QUOTE}Hi ${MODIFIER_LETTER_APOSTROPHE}Trout!${RIGHT_DOUBLE_QUOTE}`],
       [`${LEFT_DOUBLE_QUOTE}scope insensitivity${RIGHT_DOUBLE_QUOTE}`, `${LEFT_DOUBLE_QUOTE}scope insensitivity${RIGHT_DOUBLE_QUOTE}`],
       [
         '"how many ways can this function be implemented?".',
         `${LEFT_DOUBLE_QUOTE}how many ways can this function be implemented?${RIGHT_DOUBLE_QUOTE}.`,
       ],
       ['SSL.")', `SSL.${RIGHT_DOUBLE_QUOTE})`],
-      ["can't multiply\"?", `can${RIGHT_SINGLE_QUOTE}t multiply${RIGHT_DOUBLE_QUOTE}?`],
+      ["can't multiply\"?", `can${MODIFIER_LETTER_APOSTROPHE}t multiply${RIGHT_DOUBLE_QUOTE}?`],
       ['with "scope insensitivity":', `with ${LEFT_DOUBLE_QUOTE}scope insensitivity${RIGHT_DOUBLE_QUOTE}:`],
       ['("the best")', `(${LEFT_DOUBLE_QUOTE}the best${RIGHT_DOUBLE_QUOTE})`],
       ['"This is a quote"...', `${LEFT_DOUBLE_QUOTE}This is a quote${RIGHT_DOUBLE_QUOTE}...`],
@@ -49,7 +53,7 @@ describe("niceQuotes", () => {
       // End-of-line quote becomes RIGHT quote
       ['not confident in that plan - "', `not confident in that plan - ${RIGHT_DOUBLE_QUOTE}`],
     ])('should convert double quotes in "%s"', (input, expected) => {
-      expect(niceQuotes(input)).toBe(expected)
+      expect(niceQuotes(input, MLA)).toBe(expected)
     })
   })
 
@@ -57,16 +61,16 @@ describe("niceQuotes", () => {
     it.each([
       ["He said, 'Hi'", `He said, ${LEFT_SINGLE_QUOTE}Hi${RIGHT_SINGLE_QUOTE}`],
       ["He wanted 'power.'", `He wanted ${LEFT_SINGLE_QUOTE}power.${RIGHT_SINGLE_QUOTE}`],
-      ["I'd", `I${RIGHT_SINGLE_QUOTE}d`],
-      ["I don't'nt want to go", `I don${RIGHT_SINGLE_QUOTE}t${RIGHT_SINGLE_QUOTE}nt want to go`],
-      ['"\'sup"', `${LEFT_DOUBLE_QUOTE}${RIGHT_SINGLE_QUOTE}sup${RIGHT_DOUBLE_QUOTE}`],
-      ["'SUP", `${RIGHT_SINGLE_QUOTE}SUP`],
-      ["Rock 'n' Roll", `Rock ${RIGHT_SINGLE_QUOTE}n${RIGHT_SINGLE_QUOTE} Roll`],
-      ["I was born in '99", `I was born in ${RIGHT_SINGLE_QUOTE}99`],
-      ["'99 tigers weren't a match", `${RIGHT_SINGLE_QUOTE}99 tigers weren${RIGHT_SINGLE_QUOTE}t a match`],
+      ["I'd", `I${MODIFIER_LETTER_APOSTROPHE}d`],
+      ["I don't'nt want to go", `I don${MODIFIER_LETTER_APOSTROPHE}t${MODIFIER_LETTER_APOSTROPHE}nt want to go`],
+      ['"\'sup"', `${LEFT_DOUBLE_QUOTE}${MODIFIER_LETTER_APOSTROPHE}sup${RIGHT_DOUBLE_QUOTE}`],
+      ["'SUP", `${MODIFIER_LETTER_APOSTROPHE}SUP`],
+      ["Rock 'n' Roll", `Rock ${MODIFIER_LETTER_APOSTROPHE}n${MODIFIER_LETTER_APOSTROPHE} Roll`],
+      ["I was born in '99", `I was born in ${MODIFIER_LETTER_APOSTROPHE}99`],
+      ["'99 tigers weren't a match", `${MODIFIER_LETTER_APOSTROPHE}99 tigers weren${MODIFIER_LETTER_APOSTROPHE}t a match`],
       [
         "I'm not the best, haven't you heard?",
-        `I${RIGHT_SINGLE_QUOTE}m not the best, haven${RIGHT_SINGLE_QUOTE}t you heard?`,
+        `I${MODIFIER_LETTER_APOSTROPHE}m not the best, haven${MODIFIER_LETTER_APOSTROPHE}t you heard?`,
       ],
       // Skipped: Complex edge case with 'sup and quoted phrase
       // ["Hey, 'sup 'this is a single quote'", `Hey, ${RIGHT_SINGLE_QUOTE}sup ${LEFT_SINGLE_QUOTE}this is a single quote${RIGHT_SINGLE_QUOTE}`],
@@ -79,24 +83,92 @@ describe("niceQuotes", () => {
       ["('survival incentive')", `(${LEFT_SINGLE_QUOTE}survival incentive${RIGHT_SINGLE_QUOTE})`],
       [
         "strategy s's return is good, even as d's return is bad",
-        `strategy s${RIGHT_SINGLE_QUOTE}s return is good, even as d${RIGHT_SINGLE_QUOTE}s return is bad`,
+        `strategy s${MODIFIER_LETTER_APOSTROPHE}s return is good, even as d${MODIFIER_LETTER_APOSTROPHE}s return is bad`,
       ],
+      // Possessive plural (trailing apostrophe → closing RSQ)
+      ["the dogs' owner", `the dogs${RIGHT_SINGLE_QUOTE} owner`],
+      ["the bosses' meeting", `the bosses${RIGHT_SINGLE_QUOTE} meeting`],
+      // Chained possessives
+      ["the dog's owner's car", `the dog${MODIFIER_LETTER_APOSTROPHE}s owner${MODIFIER_LETTER_APOSTROPHE}s car`],
+      // Hyphenated possessive
+      ["mother-in-law's house", `mother-in-law${MODIFIER_LETTER_APOSTROPHE}s house`],
+      // Accented character before possessive
+      ["café's menu", `café${MODIFIER_LETTER_APOSTROPHE}s menu`],
+      // Digit before possessive
+      ["the 747's engine", `the 747${MODIFIER_LETTER_APOSTROPHE}s engine`],
+      // Compound contraction + possessive
+      ["shouldn't's", `shouldn${MODIFIER_LETTER_APOSTROPHE}t${MODIFIER_LETTER_APOSTROPHE}s`],
+      // Contraction before em-dash
+      [`don't${EM_DASH}stop`, `don${MODIFIER_LETTER_APOSTROPHE}t${EM_DASH}stop`],
+      // Contraction + digit context
+      ["it's 5 o'clock", `it${MODIFIER_LETTER_APOSTROPHE}s 5 o${MODIFIER_LETTER_APOSTROPHE}clock`],
+      // French contractions (single-letter prefix + accented Latin)
+      ["l'homme", `l${MODIFIER_LETTER_APOSTROPHE}homme`],
+      ["l'école", `l${MODIFIER_LETTER_APOSTROPHE}école`],
+      // Uppercase contractions and names
+      ["O'NEILL", `O${MODIFIER_LETTER_APOSTROPHE}NEILL`],
+      ["CAN'T", `CAN${MODIFIER_LETTER_APOSTROPHE}T`],
+      // Possessive in parenthetical
+      ["(Brien's)", `(Brien${MODIFIER_LETTER_APOSTROPHE}s)`],
+      // Possessive inside single-quoted phrase
+      ["'the dog's bowl'", `${LEFT_SINGLE_QUOTE}the dog${MODIFIER_LETTER_APOSTROPHE}s bowl${RIGHT_SINGLE_QUOTE}`],
+      // Straight apostrophe inside pre-converted double quotes
+      [`${LEFT_DOUBLE_QUOTE}the dog's${RIGHT_DOUBLE_QUOTE}`, `${LEFT_DOUBLE_QUOTE}the dog${MODIFIER_LETTER_APOSTROPHE}s${RIGHT_DOUBLE_QUOTE}`],
+      // Decade in double quotes
+      [`"the '90s"`, `${LEFT_DOUBLE_QUOTE}the ${MODIFIER_LETTER_APOSTROPHE}90s${RIGHT_DOUBLE_QUOTE}`],
+      // 'n' + possessive combination
+      ["Rock 'n' Roll's greatest hits", `Rock ${MODIFIER_LETTER_APOSTROPHE}n${MODIFIER_LETTER_APOSTROPHE} Roll${MODIFIER_LETTER_APOSTROPHE}s greatest hits`],
+      // Non-Latin character before possessive
+      ["Привет's", `Привет${MODIFIER_LETTER_APOSTROPHE}s`],
+      // Closing RSQ then opening LDQ
+      [`'hello' "world"`, `${LEFT_SINGLE_QUOTE}hello${RIGHT_SINGLE_QUOTE} ${LEFT_DOUBLE_QUOTE}world${RIGHT_DOUBLE_QUOTE}`],
     ])('should handle single quotes/apostrophes in "%s"', (input, expected) => {
-      expect(niceQuotes(input)).toBe(expected)
+      expect(niceQuotes(input, MLA)).toBe(expected)
     })
   })
 
   describe("leading apostrophe contractions", () => {
     it.each([
-      ["'twas the night", `${RIGHT_SINGLE_QUOTE}twas the night`],
-      ["'tis the season", `${RIGHT_SINGLE_QUOTE}tis the season`],
-      ["'Twas brillig", `${RIGHT_SINGLE_QUOTE}Twas brillig`],
-      ["'Tis but a scratch", `${RIGHT_SINGLE_QUOTE}Tis but a scratch`],
+      ["'twas the night", `${MODIFIER_LETTER_APOSTROPHE}twas the night`],
+      ["'tis the season", `${MODIFIER_LETTER_APOSTROPHE}tis the season`],
+      ["'Twas brillig", `${MODIFIER_LETTER_APOSTROPHE}Twas brillig`],
+      ["'Tis but a scratch", `${MODIFIER_LETTER_APOSTROPHE}Tis but a scratch`],
       // Decade abbreviations
-      ["the '90s", `the ${RIGHT_SINGLE_QUOTE}90s`],
-      ["in '99", `in ${RIGHT_SINGLE_QUOTE}99`],
+      ["the '90s", `the ${MODIFIER_LETTER_APOSTROPHE}90s`],
+      ["in '99", `in ${MODIFIER_LETTER_APOSTROPHE}99`],
+      ["the '00s", `the ${MODIFIER_LETTER_APOSTROPHE}00s`],
+      // Additional leading contractions
+      ["'cause", `${MODIFIER_LETTER_APOSTROPHE}cause`],
+      ["'twas the night, 'twas indeed", `${MODIFIER_LETTER_APOSTROPHE}twas the night, ${MODIFIER_LETTER_APOSTROPHE}twas indeed`],
+      [`"'twas the night"`, `${LEFT_DOUBLE_QUOTE}${MODIFIER_LETTER_APOSTROPHE}twas the night${RIGHT_DOUBLE_QUOTE}`],
     ])('handles leading apostrophe in "%s"', (input, expected) => {
-      expect(niceQuotes(input)).toBe(expected)
+      expect(niceQuotes(input, MLA)).toBe(expected)
+    })
+
+    it("multiple decades in one sentence", () => {
+      expect(niceQuotes("The '60s, '70s, and '80s were different.", MLA)).toBe(
+        `The ${MODIFIER_LETTER_APOSTROPHE}60s, ${MODIFIER_LETTER_APOSTROPHE}70s, and ${MODIFIER_LETTER_APOSTROPHE}80s were different.`
+      )
+    })
+  })
+
+  describe("'n' abbreviation edge cases", () => {
+    it.each([
+      ["uppercase 'N' is not abbreviated", "Rock 'N' Roll", `Rock ${LEFT_SINGLE_QUOTE}N${RIGHT_SINGLE_QUOTE} Roll`],
+      ["multiple 'n' abbreviations", "Rock 'n' Roll and fish 'n' chips", `Rock ${MODIFIER_LETTER_APOSTROPHE}n${MODIFIER_LETTER_APOSTROPHE} Roll and fish ${MODIFIER_LETTER_APOSTROPHE}n${MODIFIER_LETTER_APOSTROPHE} chips`],
+      ["digit neighbors (\\w includes digits)", "1 'n' 2", `1 ${MODIFIER_LETTER_APOSTROPHE}n${MODIFIER_LETTER_APOSTROPHE} 2`],
+      ["known false positive: quoted letter", "the letter 'n' is common", `the letter ${MODIFIER_LETTER_APOSTROPHE}n${MODIFIER_LETTER_APOSTROPHE} is common`],
+    ])('%s', (_label, input, expected) => {
+      expect(niceQuotes(input, MLA)).toBe(expected)
+    })
+
+    it.each([
+      ["start of string (no preceding word)", "'n' Roll", `${LEFT_SINGLE_QUOTE}n${RIGHT_SINGLE_QUOTE} Roll`],
+      ["end of string (no following word)", "Rock 'n'", `Rock ${LEFT_SINGLE_QUOTE}n${RIGHT_SINGLE_QUOTE}`],
+      ["punctuation precedes first apostrophe", "said, 'n' is good", `said, ${LEFT_SINGLE_QUOTE}n${RIGHT_SINGLE_QUOTE} is good`],
+      ["newline replaces space", "Rock 'n'\nRoll", `Rock ${LEFT_SINGLE_QUOTE}n${RIGHT_SINGLE_QUOTE}\nRoll`],
+    ])('does not produce MLA-n-MLA: %s', (_label, input, expected) => {
+      expect(niceQuotes(input, MLA)).toBe(expected)
     })
   })
 
@@ -137,11 +209,11 @@ describe("niceQuotes", () => {
 
     // From Standard Ebooks: M'Donald-style names (archaic patterns)
     it.each([
-      [`"M'Lord"`, `${LEFT_DOUBLE_QUOTE}M${RIGHT_SINGLE_QUOTE}Lord${RIGHT_DOUBLE_QUOTE}`],
-      [`O'Brien's idea`, `O${RIGHT_SINGLE_QUOTE}Brien${RIGHT_SINGLE_QUOTE}s idea`],
-      [`The O'Connors`, `The O${RIGHT_SINGLE_QUOTE}Connors`],
+      [`"M'Lord"`, `${LEFT_DOUBLE_QUOTE}M${MODIFIER_LETTER_APOSTROPHE}Lord${RIGHT_DOUBLE_QUOTE}`],
+      [`O'Brien's idea`, `O${MODIFIER_LETTER_APOSTROPHE}Brien${MODIFIER_LETTER_APOSTROPHE}s idea`],
+      [`The O'Connors`, `The O${MODIFIER_LETTER_APOSTROPHE}Connors`],
     ])('handles Irish/Scottish name apostrophes: "%s"', (input, expected) => {
-      expect(niceQuotes(input)).toBe(expected)
+      expect(niceQuotes(input, MLA)).toBe(expected)
     })
 
     // From smartquotes.js: complex nested quotes
@@ -165,17 +237,17 @@ describe("niceQuotes", () => {
   describe("complex real-world patterns", () => {
     it.each([
       // Dialogue with attribution
-      ['"I can\'t," she said.', `${LEFT_DOUBLE_QUOTE}I can${RIGHT_SINGLE_QUOTE}t,${RIGHT_DOUBLE_QUOTE} she said.`],
+      ['"I can\'t," she said.', `${LEFT_DOUBLE_QUOTE}I can${MODIFIER_LETTER_APOSTROPHE}t,${RIGHT_DOUBLE_QUOTE} she said.`],
       ['"Why not?" he asked.', `${LEFT_DOUBLE_QUOTE}Why not?${RIGHT_DOUBLE_QUOTE} he asked.`],
       // Multiple contractions
-      ["I'm can't won't don't", `I${RIGHT_SINGLE_QUOTE}m can${RIGHT_SINGLE_QUOTE}t won${RIGHT_SINGLE_QUOTE}t don${RIGHT_SINGLE_QUOTE}t`],
+      ["I'm can't won't don't", `I${MODIFIER_LETTER_APOSTROPHE}m can${MODIFIER_LETTER_APOSTROPHE}t won${MODIFIER_LETTER_APOSTROPHE}t don${MODIFIER_LETTER_APOSTROPHE}t`],
       // Quote within parentheses
       ['("test")', `(${LEFT_DOUBLE_QUOTE}test${RIGHT_DOUBLE_QUOTE})`],
       ["('test')", `(${LEFT_SINGLE_QUOTE}test${RIGHT_SINGLE_QUOTE})`],
       // Quote with slash separator
       ['"option1"/"option2"', `${LEFT_DOUBLE_QUOTE}option1${RIGHT_DOUBLE_QUOTE}/${LEFT_DOUBLE_QUOTE}option2${RIGHT_DOUBLE_QUOTE}`],
     ])('handles complex pattern: "%s"', (input, expected) => {
-      expect(niceQuotes(input)).toBe(expected)
+      expect(niceQuotes(input, MLA)).toBe(expected)
     })
 
     it("handles multi-line dialogue", () => {
@@ -189,22 +261,46 @@ describe("niceQuotes", () => {
     it.each([
       `${LEFT_DOUBLE_QUOTE}already curly${RIGHT_DOUBLE_QUOTE}`,
       `${LEFT_SINGLE_QUOTE}single curly${RIGHT_SINGLE_QUOTE}`,
-      `I${RIGHT_SINGLE_QUOTE}m already converted`,
+      `I${MODIFIER_LETTER_APOSTROPHE}m already converted`,
       `${LEFT_DOUBLE_QUOTE}nested ${LEFT_SINGLE_QUOTE}quotes${RIGHT_SINGLE_QUOTE}${RIGHT_DOUBLE_QUOTE}`,
+      // French contractions
+      `l${MODIFIER_LETTER_APOSTROPHE}homme d${MODIFIER_LETTER_APOSTROPHE}accord`,
+      // Uppercase
+      `O${MODIFIER_LETTER_APOSTROPHE}NEILL`,
+      `CAN${MODIFIER_LETTER_APOSTROPHE}T`,
+      // Plural possessive
+      `the dogs${RIGHT_SINGLE_QUOTE} owner`,
+      // Mixed quote types
+      `${LEFT_SINGLE_QUOTE}hello${RIGHT_SINGLE_QUOTE} ${LEFT_DOUBLE_QUOTE}world${RIGHT_DOUBLE_QUOTE}`,
     ])('is idempotent for: "%s"', (input) => {
-      expect(niceQuotes(input)).toBe(input)
-      expect(niceQuotes(niceQuotes(input))).toBe(input)
+      expect(niceQuotes(input, MLA)).toBe(input)
+      expect(niceQuotes(niceQuotes(input, MLA), MLA)).toBe(input)
     })
   })
 
   describe("with separator character", () => {
-    const sep = "\uE000"
+    const sep = DEFAULT_SEPARATOR
     it.each([
       [`"Hello${sep} world"`, `${LEFT_DOUBLE_QUOTE}Hello${sep} world${RIGHT_DOUBLE_QUOTE}`, "preserves separator positions"],
-      [`don${sep}'t`, `don${sep}${RIGHT_SINGLE_QUOTE}t`, "contractions across separator"],
+      [`don${sep}'t`, `don${sep}${MODIFIER_LETTER_APOSTROPHE}t`, "contractions across separator"],
       [`"test${sep}"`, `${LEFT_DOUBLE_QUOTE}test${sep}${RIGHT_DOUBLE_QUOTE}`, "quotes at separator boundaries"],
+      // Possessive across separator
+      [`dog${sep}'s bone`, `dog${sep}${MODIFIER_LETTER_APOSTROPHE}s bone`, "possessive across separator"],
+      // Separator between apostrophe and s
+      [`the dog'${sep}s bone`, `the dog${MODIFIER_LETTER_APOSTROPHE}${sep}s bone`, "separator between apostrophe and s"],
+      // Opening after separator
+      [`${sep}'hello'`, `${sep}${LEFT_SINGLE_QUOTE}hello${RIGHT_SINGLE_QUOTE}`, "opening quote after separator"],
+      // Closing after separator
+      [`'hello${sep}'`, `${LEFT_SINGLE_QUOTE}hello${sep}${RIGHT_SINGLE_QUOTE}`, "closing quote after separator"],
     ])("%s → %s (%s)", (input, expected) => {
-      expect(niceQuotes(input, { separator: sep })).toBe(expected)
+      expect(niceQuotes(input, { separator: sep, ...MLA })).toBe(expected)
+    })
+
+    it("'n' with separators around word boundaries", () => {
+      const input = `Rock${sep} 'n' ${sep}Roll`
+      const expected = `Rock${sep} ${MODIFIER_LETTER_APOSTROPHE}n${MODIFIER_LETTER_APOSTROPHE} ${sep}Roll`
+      expect(niceQuotes(input, { separator: sep, ...MLA })).toBe(expected)
+      expect(niceQuotes(expected, { separator: sep, ...MLA })).toBe(expected)
     })
   })
 
@@ -213,8 +309,14 @@ describe("niceQuotes", () => {
       ['"unclosed', `${LEFT_DOUBLE_QUOTE}unclosed`],
       ["unclosed'", `unclosed${RIGHT_SINGLE_QUOTE}`],
       ['""', `${LEFT_DOUBLE_QUOTE}${RIGHT_DOUBLE_QUOTE}`],
+      // Minimal inputs
+      ["", ""],
+      [" ", " "],
+      ["'", `${MODIFIER_LETTER_APOSTROPHE}`],
+      ["'a", `${MODIFIER_LETTER_APOSTROPHE}a`],
+      ["a'", `a${RIGHT_SINGLE_QUOTE}`],
     ])('handles edge quote pattern: "%s"', (input, expected) => {
-      expect(niceQuotes(input)).toBe(expected)
+      expect(niceQuotes(input, MLA)).toBe(expected)
     })
   })
 
@@ -233,12 +335,12 @@ describe("niceQuotes", () => {
 
   describe("consecutive contractions", () => {
     it.each([
-      ["I'd've", `I${RIGHT_SINGLE_QUOTE}d${RIGHT_SINGLE_QUOTE}ve`],
-      ["y'all'd've", `y${RIGHT_SINGLE_QUOTE}all${RIGHT_SINGLE_QUOTE}d${RIGHT_SINGLE_QUOTE}ve`],
-      ["wouldn't've", `wouldn${RIGHT_SINGLE_QUOTE}t${RIGHT_SINGLE_QUOTE}ve`],
-      ["couldn't've", `couldn${RIGHT_SINGLE_QUOTE}t${RIGHT_SINGLE_QUOTE}ve`],
+      ["I'd've", `I${MODIFIER_LETTER_APOSTROPHE}d${MODIFIER_LETTER_APOSTROPHE}ve`],
+      ["y'all'd've", `y${MODIFIER_LETTER_APOSTROPHE}all${MODIFIER_LETTER_APOSTROPHE}d${MODIFIER_LETTER_APOSTROPHE}ve`],
+      ["wouldn't've", `wouldn${MODIFIER_LETTER_APOSTROPHE}t${MODIFIER_LETTER_APOSTROPHE}ve`],
+      ["couldn't've", `couldn${MODIFIER_LETTER_APOSTROPHE}t${MODIFIER_LETTER_APOSTROPHE}ve`],
     ])('handles double contraction: "%s"', (input, expected) => {
-      expect(niceQuotes(input)).toBe(expected)
+      expect(niceQuotes(input, MLA)).toBe(expected)
     })
   })
 
@@ -258,8 +360,12 @@ describe("niceQuotes", () => {
     it.each([
       ['"Hello\nWorld"', `${LEFT_DOUBLE_QUOTE}Hello\nWorld${RIGHT_DOUBLE_QUOTE}`],
       ['"A"\n"B"', `${LEFT_DOUBLE_QUOTE}A${RIGHT_DOUBLE_QUOTE}\n${LEFT_DOUBLE_QUOTE}B${RIGHT_DOUBLE_QUOTE}`],
+      // Contractions across lines
+      ["I can't\nbelieve it's\nnot butter", `I can${MODIFIER_LETTER_APOSTROPHE}t\nbelieve it${MODIFIER_LETTER_APOSTROPHE}s\nnot butter`],
+      // Newline stops lookahead → MLA (not LSQ) since no closing quote visible
+      ["'hello\nworld'", `${MODIFIER_LETTER_APOSTROPHE}hello\nworld${RIGHT_SINGLE_QUOTE}`],
     ])('handles multiline: "%s"', (input, expected) => {
-      expect(niceQuotes(input)).toBe(expected)
+      expect(niceQuotes(input, MLA)).toBe(expected)
     })
   })
 
@@ -315,6 +421,20 @@ describe("niceQuotes", () => {
       })
     })
 
+    describe("MLA excluded from punctuation movement", () => {
+      it.each([
+        // American: MLA period/comma stay put (MLA is not a quote character)
+        [`the dog${MODIFIER_LETTER_APOSTROPHE}s.`, `the dog${MODIFIER_LETTER_APOSTROPHE}s.`, "american"],
+        [`Brien${MODIFIER_LETTER_APOSTROPHE}s,`, `Brien${MODIFIER_LETTER_APOSTROPHE}s,`, "american"],
+        // American: RSQ period/comma move inside (contrast)
+        [`${LEFT_SINGLE_QUOTE}hello${RIGHT_SINGLE_QUOTE}.`, `${LEFT_SINGLE_QUOTE}hello.${RIGHT_SINGLE_QUOTE}`, "american"],
+        // British: RSQ period moves outside (contrast)
+        [`${LEFT_SINGLE_QUOTE}hello.${RIGHT_SINGLE_QUOTE}`, `${LEFT_SINGLE_QUOTE}hello${RIGHT_SINGLE_QUOTE}.`, "british"],
+      ])('%s → %s (%s)', (input, expected, style) => {
+        expect(niceQuotes(input, { punctuationStyle: style as "american" | "british", ...MLA })).toBe(expected)
+      })
+    })
+
     describe('when "none"', () => {
       it.each([
         [periodOutsideDouble],
@@ -339,4 +459,88 @@ describe("niceQuotes", () => {
     })
   })
 
+  describe("useModifierLetterApostrophe option", () => {
+    const RSQ = RIGHT_SINGLE_QUOTE
+
+    it.each([
+      ["contractions", "don't", `don${RSQ}t`],
+      ["possessives", "the dog's bone", `the dog${RSQ}s bone`],
+      ["O'Brien-style names", "O'Brien's idea", `O${RSQ}Brien${RSQ}s idea`],
+      ["'n' abbreviation", "Rock 'n' Roll", `Rock ${RSQ}n${RSQ} Roll`],
+      ["decades", "the '90s", `the ${RSQ}90s`],
+      ["leading apostrophes", "'twas", `${RSQ}twas`],
+    ])('defaults to RSQ for %s', (_label, input, expected) => {
+      expect(niceQuotes(input)).toBe(expected)
+    })
+
+    it("uses MLA when option is true", () => {
+      expect(niceQuotes("don't", MLA)).toBe(`don${MODIFIER_LETTER_APOSTROPHE}t`)
+    })
+
+    it("RSQ output is idempotent", () => {
+      const inputs = ["don't", "the dog's", "O'Brien", "Rock 'n' Roll", "'90s"]
+      for (const input of inputs) {
+        const first = niceQuotes(input)
+        expect(niceQuotes(first)).toBe(first)
+      }
+    })
+
+    it("MLA output is idempotent", () => {
+      const inputs = ["don't", "the dog's", "O'Brien", "Rock 'n' Roll", "'90s"]
+      for (const input of inputs) {
+        const first = niceQuotes(input, MLA)
+        expect(niceQuotes(first, MLA)).toBe(first)
+      }
+    })
+
+    describe("RSQ→MLA normalization (external system input)", () => {
+      it.each([
+        [`don${RIGHT_SINGLE_QUOTE}t`, `don${MODIFIER_LETTER_APOSTROPHE}t`],
+        [`I${RIGHT_SINGLE_QUOTE}m`, `I${MODIFIER_LETTER_APOSTROPHE}m`],
+        [`they${RIGHT_SINGLE_QUOTE}re`, `they${MODIFIER_LETTER_APOSTROPHE}re`],
+        [`O${RIGHT_SINGLE_QUOTE}Brien`, `O${MODIFIER_LETTER_APOSTROPHE}Brien`],
+        [`the dog${RIGHT_SINGLE_QUOTE}s bone`, `the dog${MODIFIER_LETTER_APOSTROPHE}s bone`],
+        // Mixed MLA + RSQ in same text
+        [`I${MODIFIER_LETTER_APOSTROPHE}m fine and you${RIGHT_SINGLE_QUOTE}re great`, `I${MODIFIER_LETTER_APOSTROPHE}m fine and you${MODIFIER_LETTER_APOSTROPHE}re great`],
+      ])('normalizes RSQ contraction "%s"', (input, expected) => {
+        expect(niceQuotes(input, MLA)).toBe(expected)
+      })
+
+      it("does NOT normalize RSQ when it is a closing quote", () => {
+        const input = `${LEFT_SINGLE_QUOTE}hello${RIGHT_SINGLE_QUOTE} world`
+        expect(niceQuotes(input, MLA)).toBe(input)
+      })
+
+      it("does not convert RSQ after non-Latin character", () => {
+        const input = `[test]${RIGHT_SINGLE_QUOTE}`
+        expect(niceQuotes(input, MLA)).toBe(input)
+      })
+    })
+  })
+
+  describe("pathological inputs", () => {
+    it("handles 1500-char input without closing quote", () => {
+      const input = `'${"a".repeat(1500)}`
+      const start = performance.now()
+      const result = niceQuotes(input, MLA)
+      expect(performance.now() - start).toBeLessThan(1000)
+      expect(niceQuotes(result, MLA)).toBe(result)
+    })
+
+    it("handles 16 rapid apostrophes", () => {
+      const input = "a'b'c'd'e'f'g'h'i'j'k'l'm'n'o'p"
+      const expected = `a${MODIFIER_LETTER_APOSTROPHE}b${MODIFIER_LETTER_APOSTROPHE}c${MODIFIER_LETTER_APOSTROPHE}d${MODIFIER_LETTER_APOSTROPHE}e${MODIFIER_LETTER_APOSTROPHE}f${MODIFIER_LETTER_APOSTROPHE}g${MODIFIER_LETTER_APOSTROPHE}h${MODIFIER_LETTER_APOSTROPHE}i${MODIFIER_LETTER_APOSTROPHE}j${MODIFIER_LETTER_APOSTROPHE}k${MODIFIER_LETTER_APOSTROPHE}l${MODIFIER_LETTER_APOSTROPHE}m${MODIFIER_LETTER_APOSTROPHE}n${MODIFIER_LETTER_APOSTROPHE}o${MODIFIER_LETTER_APOSTROPHE}p`
+      const start = performance.now()
+      const result = niceQuotes(input, MLA)
+      expect(performance.now() - start).toBeLessThan(1000)
+      expect(result).toBe(expected)
+      expect(niceQuotes(result, MLA)).toBe(result)
+    })
+
+    it("handles 500-char word + possessive", () => {
+      const input = `${"a".repeat(500)}'s thing`
+      expect(niceQuotes(input, MLA)).toBe(`${"a".repeat(500)}${MODIFIER_LETTER_APOSTROPHE}s thing`)
+    })
+  })
+
 })

package/src/tests/remark.test.ts

@@ -48,7 +48,7 @@ describe("remarkPunctilio", () => {
   describe("basic transformations (nbsp enabled)", () => {
     it.each([
       ["quotes", '"Hello," she said.', `${LDQ}Hello,${RDQ} she${NBSP}said.`],
-      ["apostrophes", "It's a test.", `It${RSQ}s${NBSP}a${NBSP}test.`],
+      ["apostrophes", "It's a test.", `It${RSQ}s a${NBSP}test.`],
       ["em dashes", "Wait -- here it comes.", `Wait${EM_DASH}here it${NBSP}comes.`],
       ["en dashes (number range)", "Pages 1-5", `Pages${NBSP}1${EN_DASH}5`],
       ["ellipses", "Wait...", `Wait${ELLIPSIS}`],