From 4ac8d0886167a9e6bf0770addb11e97eb620eca8 Mon Sep 17 00:00:00 2001
From: Alex Southwell <4596216+saphid@users.noreply.github.com>
Date: Tue, 3 Nov 2026 12:01:05 +1100
Subject: [PATCH] fix(web): PDF find matches curly quotes when you type
 straight ones

Co-Authored-By: Claude Opus 5.5 <noreply@anthropic.com>
---
 apps/web/src/components/files/pdfLayout.test.ts | 13 +++++++++++++
 apps/web/src/components/files/pdfLayout.ts      | 14 +++++++++-----
 2 files changed, 22 insertions(+), 5 deletions(-)

diff --git a/apps/web/src/components/files/pdfLayout.test.ts b/apps/web/src/components/files/pdfLayout.test.ts
index 5a57be1de95c0..9aff44bede12c 100644
--- a/apps/web/src/components/files/pdfLayout.test.ts
+++ b/apps/web/src/components/files/pdfLayout.test.ts
@@ -136,6 +136,19 @@ describe("pdfFindMatchRuns", () => {
     expect(pdfFindIncludes(page, " ")).toBe(false);
   });
 
+  it("matches straight quotes typed for typeset curly ones", () => {
+    expect(pdfFindMatchRuns(["We don\u2019t ", "ship \u201cbeta\u201d"], "don't")).toEqual([
+      true,
+      false,
+    ]);
+    expect(pdfFindMatchRuns(["We don\u2019t ", "ship \u201cbeta\u201d"], '"beta"')).toEqual([
+      false,
+      true,
+    ]);
+    expect(pdfFindIncludes("We don\u2019t ship \u201cbeta\u201d", 'don\'t ship "beta"')).toBe(true);
+    expect(pdfFindIncludes("We don't ship", "don\u2019t")).toBe(true);
+  });
+
   it("highlights nothing for a blank or missing query", () => {
     expect(pdfFindMatchRuns(["a b", "c"], " ")).toEqual([false, false]);
     expect(pdfFindMatchRuns(["a b", "c"], "")).toEqual([false, false]);
diff --git a/apps/web/src/components/files/pdfLayout.ts b/apps/web/src/components/files/pdfLayout.ts
index 451af886fb67b..eb32d982e89d0 100644
--- a/apps/web/src/components/files/pdfLayout.ts
+++ b/apps/web/src/components/files/pdfLayout.ts
@@ -56,6 +56,11 @@ export function pdfPageText(
   return items.map((item) => ("str" in item ? item.str + (item.hasEOL ? "\n" : "") : "")).join("");
 }
 
+// A typed straight quote finds a typeset curly one, as pdf.js's own find does.
+function foldQuotes(text: string) {
+  return text.replace(/[\u2018-\u201b]/g, "'").replace(/[\u201c-\u201f]/g, '"');
+}
+
 /**
  * Lowercased search text with each whitespace run, line ends included, read as one space, and a
  * hyphen that ends a line between letters dropped, as pdf.js's own find does. `owner` maps each
@@ -63,7 +68,7 @@ export function pdfPageText(
  */
 function pdfFindText(runs: readonly string[]) {
   const chars = runs.flatMap((run, index) =>
-    Array.from(run.toLowerCase(), (char) => ({ char, run: index })),
+    Array.from(foldQuotes(run.toLowerCase()), (char) => ({ char, run: index })),
   );
   let text = "";
   let last = "";
@@ -95,10 +100,9 @@ function pdfFindText(runs: readonly string[]) {
 /** Whether a page's text holds the query, under the same rules as `pdfFindMatchRuns`, without
  * mapping characters back to runs: the page scan checks every page on each query. */
 export function pdfFindIncludes(text: string, query: string) {
-  const needle = query.toLowerCase().replace(/\s+/g, " ");
+  const needle = foldQuotes(query.toLowerCase()).replace(/\s+/g, " ");
   if (!needle.trim()) return false;
-  return text
-    .toLowerCase()
+  return foldQuotes(text.toLowerCase())
     .replace(/(\p{L})-\n(?=\p{L})/gu, "$1")
     .replace(/\s+/g, " ")
     .includes(needle);
@@ -107,7 +111,7 @@ export function pdfFindIncludes(text: string, query: string) {
 /** Which text runs hold part of a case-insensitive match, when pdf.js splits words across spans. */
 export function pdfFindMatchRuns(runs: readonly string[], query: string) {
   const { text, owner } = pdfFindText(runs);
-  const needle = query.toLowerCase().replace(/\s+/g, " ");
+  const needle = foldQuotes(query.toLowerCase()).replace(/\s+/g, " ");
   const hits = runs.map(() => false);
   if (!needle.trim()) return hits;
   for (