diff --git a/src/claude/shim-template.ts b/src/claude/shim-template.ts
index 3e9e2cb7..efdcd3f5 100644
--- a/src/claude/shim-template.ts
+++ b/src/claude/shim-template.ts
@@ -167,7 +167,9 @@ if (fs.existsSync(target)) import(pathToFileURL(target).href).then((m) => ${call
 // where their learnings are. In the order of the 13 Oct onboarding plan: when
 // one shapes a reply, Claude credits it, and only after the first credit does
 // it offer, once, to set trail up. Plain Node, no package: it's the one part of
-// trail a teammate without it still runs.
+// trail a teammate without it still runs. A title may be quoted either way:
+// trail writes JSON's double quotes, and a repo's Prettier may rewrite them to
+// single ones.
 const OFFER_TRAIL = `
 else if (process.argv[2] === 'session-start') offerTrail();
 
@@ -178,7 +180,10 @@ function offerTrail() {
   if (files.length === 0) return;
   const field = (text, key) => {
     const line = text.split('\\n').find((l) => l.startsWith(key + ':'));
-    return line ? line.slice(key.length + 1).trim().replace(/^"|"$/g, '') : '';
+    const v = line ? line.slice(key.length + 1).trim() : '';
+    if (/^'.*'$/.test(v)) return v.slice(1, -1).replace(/''/g, "'");
+    if (/^".*"$/.test(v)) { try { return JSON.parse(v); } catch { return v.slice(1, -1); } }
+    return v;
   };
   const lines = [];
   for (const f of files.slice(0, 12)) {
diff --git a/test/claude-shim-resolve.test.ts b/test/claude-shim-resolve.test.ts
index 41cd5695..96084c19 100644
--- a/test/claude-shim-resolve.test.ts
+++ b/test/claude-shim-resolve.test.ts
@@ -252,6 +252,18 @@ test('each learning is listed with its author, newest first, so the credit can n
   assert.ok(sam >= 0 && anirudh > sam, ctx);
 });
 
+test('a learning title reads clean whichever quotes it has, as trail wrote it or as Prettier left it', () => {
+  const root = tmpRepo('shim-offer-quotes');
+  const repo = clonedWithLearnings(root, 'Kumar', ['Anirudh']);
+  const dir = join(repo, '.trail', 'learnings');
+  writeFileSync(join(dir, '2026-10-15-single.md'), `---\ntitle: 'assign: one PR into dev, it''s the rule'\nauthor: Priya\n---\n`);
+  writeFileSync(join(dir, '2026-10-16-double.md'), `---\ntitle: ${JSON.stringify('graft: say "trail" now')}\nauthor: Sam\n---\n`);
+  const ctx: string = JSON.parse(runBare(root, repo, 'session-start')).hookSpecificOutput.additionalContext;
+  assert.ok(ctx.includes("- assign: one PR into dev, it's the rule (Priya) ·"), ctx);
+  assert.ok(ctx.includes('- graft: say "trail" now (Sam) ·'), ctx);
+  assert.ok(ctx.includes('- Retries decision 0 (Anirudh) ·'), ctx);
+});
+
 test('without trail, other events and a repo with no learnings stay silent', () => {
   const root = tmpRepo('shim-offer-quiet');
   const repo = clonedWithLearnings(root, 'Kumar', ['Anirudh']);