diff --git a/apps/server/src/orchestration-v2/ThreadSearch.test.ts b/apps/server/src/orchestration-v2/ThreadSearch.test.ts
index 5d816133c89c7..540cfb8645a02 100644
--- a/apps/server/src/orchestration-v2/ThreadSearch.test.ts
+++ b/apps/server/src/orchestration-v2/ThreadSearch.test.ts
@@ -791,6 +791,35 @@ it.layer(layerTest)("ThreadSearch across scripts and without the index", (it) =>
   );
 });
 
+it.layer(layerTest)("ThreadSearch without the index", (it) => {
+  it.effect("finds a curly apostrophe for a straight one and back", () =>
+    Effect.gen(function* () {
+      const projections = yield* ProjectionStore.ProjectionStoreV2;
+      const search = yield* ThreadSearch.ThreadSearch;
+      const sql = yield* SqlClient.SqlClient;
+      const project = ProjectId.make("project:scan-apostrophes");
+      const curly = ThreadId.make("thread:scan-apostrophe-curly");
+      const straight = ThreadId.make("thread:scan-apostrophe-straight");
+      yield* createProject(project);
+      yield* Effect.forEach(
+        [
+          thread(curly, project),
+          message(curly, "scan-apostrophe-curly", "user", "the gannet’s nest"),
+          thread(straight, project),
+          message(straight, "scan-apostrophe-straight", "user", "a kittiwake's nest"),
+        ],
+        projections.apply,
+        { discard: true },
+      );
+      yield* sql`DROP TABLE orchestration_v2_message_search`;
+      const threadIds = (query: string) =>
+        search.search({ query }).pipe(Effect.map(({ matches }) => matches.map((m) => m.threadId)));
+      assert.deepEqual(yield* threadIds("gannet's"), [curly]);
+      assert.deepEqual(yield* threadIds("kittiwake’s"), [straight]);
+    }),
+  );
+});
+
 it.layer(layerTest)("ThreadSearch.searchOlderSettled", (it) => {
   it.effect("returns older settled title matches in scope, then older message hits", () =>
     Effect.gen(function* () {
diff --git a/apps/server/src/orchestration-v2/ThreadSearch.ts b/apps/server/src/orchestration-v2/ThreadSearch.ts
index 62c7f4eed45ec..99934b7f47627 100644
--- a/apps/server/src/orchestration-v2/ThreadSearch.ts
+++ b/apps/server/src/orchestration-v2/ThreadSearch.ts
@@ -33,7 +33,11 @@ import {
   type ThreadSearchSubject,
 } from "@t3tools/shared/paletteSearch";
 import { threadSearchPullRequests } from "@t3tools/shared/threadPullRequests";
-import { indexedMessageCondition, nonPlaceholderMessageCondition } from "./messageSearchIndex.ts";
+import {
+  indexedMessageCondition,
+  indexedMessageText,
+  nonPlaceholderMessageCondition,
+} from "./messageSearchIndex.ts";
 import { loadOlderSettledThreadsPage } from "./ShellStream.ts";
 
 // When the user last wrote in the thread aliased `threads`, as the clients
@@ -222,7 +226,7 @@ export const messageHitsQuery = (
       AND messages.message_id NOT LIKE 'async-answer:%'
       AND NOT EXISTS (
         SELECT 1 FROM json_each(${substrings}) AS token
-        WHERE instr(lower(json_extract(messages.payload_json, '$.text')), token.value) = 0
+        WHERE instr(lower(${indexedMessageText(sql, "messages.payload_json")}), token.value) = 0
       )
     -- The index's own rowid, so FTS5 returns hits newest first and stops at
     -- the limit; ordering by the messages table's rowid sorts every hit.