fix(mail-index): local AI retrieval returned 0 hits for real questions — AND-every-token FTS matching killed on stop words

Found by a new real Electron e2e test built specifically to prove the
`local` AI class genuinely works end-to-end in the packaged desktop shell:
a real local Ollama model answering a real question, grounded in the real
encrypted SQLite/FTS5 mail index — not a browser tab, not a mock.

First run surfaced a genuine bug: toFtsMatchQuery() AND-joins every token,
which is right for a deliberate search-box query but wrong for the natural-
language questions the AI retrieval surface (/api/offline/search — see its
own module header, "THE RETRIEVAL SURFACE") actually receives. "When is
check-in for the Villa sul Lago booking, and what time?" shares almost none
of its own function words with the email that answers it, so ANDing every
token — including "when"/"is"/"for"/"the"/"and"/"what" — returned 0 hits
against an index that correctly returns the right email for "Villa sul Lago
check-in".

Fix: new toFtsMatchQueryAny() (lib/mail-index/store.ts) — drops a small,
well-known English stop-word list, OR-joins what's left, and lets the
existing bm25 ranking pick the winner among partial matches. Deliberately a
NEW function, not a change to toFtsMatchQuery itself: that one's own tests
rely on "AND"/"OR"/"NOT" surviving verbatim as literal search terms
(FTS5-keyword-injection safety) — a different guarantee than this one's job
of turning a question into a good search. search() gains a `mode: 'and' |
'any'` option (default 'and', so every existing caller is unaffected); the
offline-search route passes 'any', since its one real caller is exactly
this AI-question shape.

Also added, to make the e2e test possible at all: electron/main.ts's
VNCMAIL_TEST_FIXED_PORT — a narrow, off-by-default escape hatch so
DEV_MOCK_JMAP's JMAP_SERVER_URL can point at this same standalone server's
own /api/dev-jmap. Needed because the encrypted index's key channel
(fd-3/safeStorage) only gets wired up in startStandaloneServer()'s own
random-port launch path, never when ELECTRON_LOAD_URL bypasses it for a
plain `next dev` target — so this was the only way to exercise the real
index without a full Stalwart+SMTP Docker fixture.

Verified live in the real packaged Electron shell, not just unit tests:
real dev-mode login, real multi-round /api/offline/sync + /api/offline/reindex
(39 mail/35 calendar/23 contacts indexed), real local-discovery banner
(11 real Ollama models on this machine), real "Connect", a real question
through the real Settings UI, a real direct renderer->Ollama /api/chat call
(confirmed via network log, never proxied through this app's backend), and
the model's own answer citing the exact right fact: "Saturday 28 March at
15:00" — a fact that exists nowhere except in the one indexed email.

4 new unit tests for toFtsMatchQueryAny. Full gate: tsc clean, eslint
clean, 2502/2502 tests passing, build clean, e2e/electron-ai-local-index.spec.ts
passing against the real standalone server + real Electron + real Ollama.

app/api/offline/search/route.ts

@@ -79,7 +79,12 @@ export async function GET(request: NextRequest) {
       try {
         const stats = index.stats();
         if (!query) return { hits: [] as SearchHit[], stats };
-        return { hits: index.search({ query, types, limit }), stats: wantStats ? stats : undefined };
+        // 'any': this route is the AI/RAG retrieval surface (see module
+        // header) - its one real caller sends natural-language questions,
+        // not deliberate search-box keywords, so strict AND-every-token
+        // matching (the default) drops nearly all of them. See
+        // toFtsMatchQueryAny's docstring for the confirmed-live failure.
+        return { hits: index.search({ query, types, limit, mode: 'any' }), stats: wantStats ? stats : undefined };
       } finally {
         index.close();
       }

e2e/electron-ai-local-index.spec.ts

@@ -0,0 +1,199 @@
+import { test, expect, _electron as electron } from '@playwright/test';
+import type { ElectronApplication, Page } from '@playwright/test';
+import fs from 'node:fs';
+import os from 'node:os';
+import path from 'node:path';
+
+/**
+ * Proves the two hardest-to-fake claims about the AI Assistant's `local`
+ * class in the REAL packaged desktop shell, not a browser tab:
+ *
+ *   1. The LLM genuinely runs locally — a direct browser-side fetch to
+ *      this machine's own Ollama (127.0.0.1:11434), never proxied through
+ *      this app's backend.
+ *   2. It is genuinely grounded in the ENCRYPTED LOCAL SQLITE/FTS5 MAIL
+ *      INDEX (lib/mail-index/**), not the separate real-JMAP-embeddings
+ *      server leg (lib/ai/retrieval/mail-embeddings.ts) — AI_SERVER_BASE_URL
+ *      is deliberately left UNSET here so only the local FTS leg can
+ *      supply retrieval context. If this test passes, the local index
+ *      leg is the only possible source of the grounded answer.
+ *
+ * Needs a real launch through electron/main.ts's startStandaloneServer(),
+ * not ELECTRON_LOAD_URL — that's the only code path that wires up the
+ * fd-3 key channel / safeStorage the encrypted index depends on (see
+ * integration/tests/12-electron-mail-index.spec.ts's header for the full
+ * reasoning). That function picks a random free port every launch, which
+ * would make it impossible to also point DEV_MOCK_JMAP's JMAP_SERVER_URL
+ * at this same server's own /api/dev-jmap route — hence
+ * VNCMAIL_TEST_FIXED_PORT, a narrow, off-by-default escape hatch added to
+ * electron/main.ts specifically to make this test possible without a real
+ * Stalwart fixture.
+ *
+ * Requires a real Ollama already running on this machine with at least one
+ * completion-capable model installed — skips (not fails) otherwise, since
+ * "no local LLM on this machine" is an environment fact, not a bug.
+ */
+
+const projectRoot = path.resolve(__dirname, '..');
+const FIXED_PORT = 39217;
+const ORIGIN = `http://127.0.0.1:${FIXED_PORT}`;
+
+async function ollamaIsUp(): Promise<boolean> {
+  try {
+    const res = await fetch('http://127.0.0.1:11434/api/tags');
+    if (!res.ok) return false;
+    const body = (await res.json()) as { models?: Array<{ capabilities?: string[] }> };
+    return (body.models ?? []).some((m) => !m.capabilities || m.capabilities.includes('completion'));
+  } catch {
+    return false;
+  }
+}
+
+test.describe('Electron desktop shell - local LLM answers from the real encrypted mail index', () => {
+  let electronApp: ElectronApplication;
+  let appWindow: Page;
+  let userDataDir: string;
+
+  test.beforeAll(async () => {
+    if (!(await ollamaIsUp())) {
+      test.skip(true, 'No local Ollama with a completion-capable model reachable on this machine — environment fact, not a failure.');
+    }
+
+    userDataDir = fs.mkdtempSync(path.join(os.tmpdir(), 'vncmail-ai-index-test-'));
+
+    electronApp = await electron.launch({
+      args: [projectRoot, `--user-data-dir=${userDataDir}`],
+      env: {
+        ...process.env,
+        VNCMAIL_TEST_FIXED_PORT: String(FIXED_PORT),
+        DEV_MOCK_JMAP: 'true',
+        JMAP_SERVER_URL: `${ORIGIN}/api/dev-jmap`,
+        SESSION_SECRET: 'electron-ai-local-index-verify-32-chars-min',
+        // Deliberately UNSET: isolates grounding to the local FTS leg (see
+        // module header) — the server embeddings leg 404s cleanly instead
+        // of silently also being able to answer the question.
+        AI_SERVER_BASE_URL: '',
+        NODE_ENV: 'production',
+      },
+    });
+
+    appWindow = await electronApp.firstWindow();
+    await appWindow.waitForLoadState('domcontentloaded');
+  });
+
+  test.afterAll(async () => {
+    await electronApp?.close();
+    if (userDataDir) fs.rmSync(userDataDir, { recursive: true, force: true });
+  });
+
+  test('logs in, builds the real encrypted index, and a local Ollama model answers a mail question grounded in it', async () => {
+    // ── 1. Real dev-mode login (sets the real session cookie the offline
+    // index and every other server-side-identity feature need). ──
+    const devLoginContainer = appWindow.locator('div', { hasText: 'Dev mode - logging in as dev@localhost' }).last();
+    await devLoginContainer.getByRole('button').click();
+    await appWindow.waitForURL((url) => !url.pathname.includes('login'), { timeout: 20000 });
+
+    // ── 2. Build the real encrypted local index: delta-sync the mock
+    // account's mail into the replica store, then write it into SQLite/FTS5.
+    // Chains /api/offline/sync while unfinishedWork is true, capped so a
+    // real bug can't hang the test forever. ──
+    const syncOutcome = await appWindow.evaluate(async () => {
+      let unfinished = true;
+      let calls = 0;
+      const statuses: number[] = [];
+      while (unfinished && calls < 10) {
+        const res = await fetch('/api/offline/sync', { method: 'POST', headers: { 'Content-Type': 'application/json' }, body: '{}' });
+        statuses.push(res.status);
+        if (!res.ok) break;
+        const body = await res.json();
+        unfinished = body.unfinishedWork === true;
+        calls++;
+      }
+      const reindexRes = await fetch('/api/offline/reindex', { method: 'POST', headers: { 'Content-Type': 'application/json' }, body: JSON.stringify({ catchUp: true }) });
+      return { syncStatuses: statuses, syncCalls: calls, reindexStatus: reindexRes.status, reindexBody: await reindexRes.json().catch(() => null) };
+    });
+    console.log('[ai-local-index] sync+reindex outcome:', JSON.stringify(syncOutcome));
+    expect(syncOutcome.syncStatuses.every((s) => s === 200)).toBe(true);
+    expect(syncOutcome.reindexStatus).toBe(200);
+
+    // ── 3. Prove the local index itself is real and queryable BEFORE
+    // touching the LLM at all — isolates "is the SQLite/FTS5 index working"
+    // from "did the model use it correctly". ──
+    const directSearch = await appWindow.evaluate(async () => {
+      const res = await fetch(`/api/offline/search?q=${encodeURIComponent('Villa sul Lago check-in')}&limit=6`);
+      return { status: res.status, body: await res.json().catch(() => null) };
+    });
+    console.log('[ai-local-index] direct /api/offline/search result:', JSON.stringify(directSearch.body));
+    expect(directSearch.status, 'the encrypted local index must be reachable (200), not 404 (feature disabled) or 503 (no key channel)').toBe(200);
+    expect(directSearch.body?.ok).toBe(true);
+    const hitTitles = (directSearch.body?.hits ?? []).map((h: { title?: string }) => h.title ?? '');
+    expect(hitTitles.some((t: string) => /villa sul lago/i.test(t)), `expected a "Villa sul Lago" hit in the real index, got: ${JSON.stringify(hitTitles)}`).toBe(true);
+
+    // ── 4. Navigate to the real AI Assistant settings UI and use the
+    // local-discovery "Connect" banner — the exact flow a real user takes,
+    // proving discovery -> connect -> ask works as one integrated feature.
+    // Deliberately an in-app SPA navigation (click the real sidebar link),
+    // NOT appWindow.goto() — a full page reload drops whatever client-only
+    // session state the dev-mode login established (confirmed: goto('/settings')
+    // bounces straight back to /login even though the JMAP session cookie
+    // from step 2/3 is still valid), so the click is load-bearing, not
+    // cosmetic. ──
+    await appWindow.locator('a[href="/settings"], a[href*="/settings"]').first().click();
+    const searchBox = appWindow.locator('input[type="search"]').first();
+    await searchBox.fill('AI Assistant');
+    await appWindow.getByRole('button', { name: 'AI Assistant' }).click();
+
+    const connectButton = appWindow.getByRole('button', { name: /Connect/i });
+    await expect(connectButton, 'the local-discovery banner should appear since a real Ollama is running on this machine').toBeVisible({ timeout: 10000 });
+    const bannerText = await appWindow.locator('text=Local AI found on this machine').locator('..').innerText();
+    console.log('[ai-local-index] discovery banner text:', bannerText);
+    await connectButton.click();
+
+    // ── 5. Ask a question only answerable by combining the local LLM
+    // with the local index's actual content. ──
+    const questionBox = appWindow.getByPlaceholder(/What did legal say/i);
+    await questionBox.fill('When is check-in for the Villa sul Lago booking, and what time?');
+    const askButton = appWindow.getByRole('button', { name: /^Ask$/ });
+    await expect(askButton, 'Ask must be enabled immediately after Connect pre-fills provider+model').toBeEnabled({ timeout: 5000 });
+
+    const chatRequests: string[] = [];
+    const offlineSearchCalls: Array<{ url: string; status: number; body: unknown }> = [];
+    appWindow.on('request', (req) => {
+      if (req.url().includes('11434')) chatRequests.push(`${req.method()} ${req.url()}`);
+    });
+    appWindow.on('response', async (res) => {
+      if (res.url().includes('/api/offline/search')) {
+        offlineSearchCalls.push({ url: res.url(), status: res.status(), body: await res.json().catch(() => null) });
+      }
+    });
+
+    // Log the exact prompt Ollama actually received, straight from the
+    // request body — the ground truth for "did retrieval even fire".
+    const ollamaChatPayloads: unknown[] = [];
+    await appWindow.route('**/api/chat', async (route) => {
+      try {
+        ollamaChatPayloads.push(JSON.parse(route.request().postData() ?? 'null'));
+      } catch { /* ignore parse failure, still let the request through */ }
+      await route.continue();
+    });
+
+    await askButton.click();
+
+    const answerLocator = appWindow.locator('p.whitespace-pre-wrap').first();
+    await expect(answerLocator, 'the local Ollama model should produce an answer within a generous timeout').toBeVisible({ timeout: 60000 });
+    const answerText = await answerLocator.innerText();
+    console.log('[ai-local-index] final answer:', answerText);
+    console.log('[ai-local-index] direct-to-Ollama requests observed:', chatRequests);
+    console.log('[ai-local-index] /api/offline/search calls during Ask:', JSON.stringify(offlineSearchCalls));
+    console.log('[ai-local-index] exact payload(s) sent to Ollama /api/chat:', JSON.stringify(ollamaChatPayloads));
+
+    // The real proof: the model's own words contain the fact that only
+    // exists in the indexed email (28 March, 15:00), and the request log
+    // shows the renderer talked to Ollama's loopback address directly.
+    expect(answerText).toMatch(/28\s*march|march\s*28/i);
+    expect(answerText).toMatch(/15:00|3\s*pm|3:00\s*pm/i);
+    expect(chatRequests.some((r) => r.includes('/api/chat')), `expected a direct renderer -> Ollama /api/chat request, saw: ${JSON.stringify(chatRequests)}`).toBe(true);
+
+    await appWindow.screenshot({ path: path.join(projectRoot, 'electron-ai-local-index-result.png'), fullPage: true });
+  });
+});

electron/main.ts

@@ -173,7 +173,18 @@ async function startStandaloneServer(): Promise<string> {
     );
   }
 
-  const port = await getFreePort();
+  // Normally a random free port, chosen fresh every launch - JMAP_SERVER_URL
+  // never needs to reference it back (a real deployment's Stalwart lives at
+  // its own fixed address). VNCMAIL_TEST_FIXED_PORT is a narrow escape hatch
+  // for e2e tests that DO need to know the port ahead of time - specifically
+  // to point DEV_MOCK_JMAP's JMAP_SERVER_URL at this same standalone server's
+  // own /api/dev-jmap route, which is the only way to exercise the real
+  // encrypted offline index (lib/mail-index/**) without a real Stalwart
+  // fixture: that index's key channel only gets wired up in this function,
+  // never when ELECTRON_LOAD_URL bypasses it for a plain `next dev` target.
+  // Unset in every normal launch, so this changes nothing outside a test run.
+  const fixedPort = process.env.VNCMAIL_TEST_FIXED_PORT ? Number(process.env.VNCMAIL_TEST_FIXED_PORT) : null;
+  const port = fixedPort && Number.isInteger(fixedPort) ? fixedPort : await getFreePort();
   const url = `http://127.0.0.1:${port}`;
 
   const storeDir = getIndexStoreDir();

lib/mail-index/__tests__/store.test.ts

@@ -6,7 +6,7 @@ import { afterEach, beforeEach, describe, expect, it } from 'vitest';
 import { isSqlcipherAvailable } from '../binding';
 import type { SqlcipherConstructor, SqlcipherDatabase, SqlcipherStatement } from '../binding';
 import { accountFileToken, getStoreDir, indexDbPath, STORE_DIR_ENV } from '../paths';
-import { MailIndex, openKeyed, toFtsMatchQuery, type IndexDoc } from '../store';
+import { MailIndex, openKeyed, toFtsMatchQuery, toFtsMatchQueryAny, type IndexDoc } from '../store';
 
 describe('toFtsMatchQuery', () => {
   it('quotes every token so FTS5 operators in user input cannot break the query', () => {
@@ -48,6 +48,62 @@ describe('toFtsMatchQuery', () => {
   });
 });
 
+describe('toFtsMatchQueryAny', () => {
+  it('drops English function words and OR-joins what is left - the confirmed-live failure this fixes', () => {
+    // AND-every-token (toFtsMatchQuery) returns 0 hits for this exact
+    // question against a document that only contains "Villa sul Lago" and
+    // "check-in" - see app/api/offline/search/route.ts's comment and the
+    // e2e electron-ai-local-index.spec.ts run that first caught this.
+    const result = toFtsMatchQueryAny('When is check-in for the Villa sul Lago booking, and what time?');
+    expect(result).not.toBeNull();
+    expect(result).not.toContain(' AND ');
+    expect(result).toContain('"check-in"');
+    expect(result).toContain('"Villa"');
+    expect(result).toContain('"sul"');
+    expect(result).toContain('"Lago"');
+    expect(result).toContain('"booking"');
+    // "time" is the last surviving content word, so it gets the
+    // prefix-match star - not "Lago", which is merely the last one this
+    // test happens to name first.
+    expect(result).toContain('"time"*');
+    // Pure stop words, correctly dropped rather than OR-joined as noise that
+    // would otherwise match almost every document in a mailbox.
+    expect(result).not.toMatch(/"When"|"is"|"for"|"the"|"and"|"what"/i);
+  });
+
+  it('falls back to the unfiltered text when every word is a stop word, rather than searching for nothing', () => {
+    // "What is this" is 100% stop words - dropping all of them would leave
+    // zero tokens (a null match, meaning "return everything" is wrong for a
+    // question shaped like this); falling back to the original text at
+    // least keeps a real, if weak, query.
+    const result = toFtsMatchQueryAny('What is this');
+    expect(result).not.toBeNull();
+  });
+
+  it('still safely quotes FTS5 syntax characters even after stop-word filtering removes the surrounding noise', () => {
+    // "OR"/"NEAR" themselves are common enough as English words that this
+    // builder's stop-word list intentionally drops bare "or" (unlike
+    // toFtsMatchQuery, which preserves it verbatim - see that test's own
+    // comment on why: different concern, different guarantee). The safety
+    // property that DOES still apply here is the one that matters for a
+    // 500: whatever tokens survive filtering are always quoted before
+    // reaching FTS5, so a stray `"`/`*`/`(` in real question text can never
+    // raise a syntax error.
+    const result = toFtsMatchQueryAny('a" NEAR(bar) baz*');
+    expect(result).not.toBeNull();
+    expect(result).toContain('"NEAR"');
+    expect(result).toContain('"bar"');
+    expect(result).toContain('"baz"');
+    expect(result).not.toMatch(/fts5|syntax/i);
+  });
+
+  it('returns null for input with no usable tokens', () => {
+    expect(toFtsMatchQueryAny('')).toBeNull();
+    expect(toFtsMatchQueryAny('***')).toBeNull();
+    expect(toFtsMatchQueryAny(undefined as unknown as string)).toBeNull();
+  });
+});
+
 describe('paths', () => {
   const original = process.env[STORE_DIR_ENV];
   afterEach(() => {

lib/mail-index/store.ts

@@ -331,8 +331,12 @@ export class MailIndex {
     types?: readonly ContentType[];
     limit?: number;
     snippetTokens?: number;
+    /** 'and' (default): every token required - a deliberate search-box query.
+     *  'any': stop words dropped, remaining tokens OR-joined, ranked by bm25 -
+     *  a natural-language question (see toFtsMatchQueryAny's docstring). */
+    mode?: 'and' | 'any';
   }): SearchHit[] {
-    const match = toFtsMatchQuery(opts.query);
+    const match = opts.mode === 'any' ? toFtsMatchQueryAny(opts.query) : toFtsMatchQuery(opts.query);
     if (!match) return [];
 
     const limit = Math.min(Math.max(opts.limit ?? 20, 1), 200);
@@ -446,34 +450,85 @@ function safeParseObject(v: unknown): Record<string, unknown> {
 }
 
 /**
- * Turns arbitrary user text into a safe FTS5 MATCH expression.
+ * Splits and safely quotes raw text into FTS5-safe tokens, shared by both
- *
+ * query-builders below. Split on anything that isn't a word character or an
- * FTS5's query syntax is not SQL, so parameter binding does NOT protect it: a
+ * intra-word mark - keeps unicode letters (so "Müller" and "東京" survive)
- * bare `"` or a stray `*`/`NEAR`/`:` in user input raises
+ * via the u flag. Every token is quoted (making it a literal phrase) so a
- * `fts5: syntax error`, which would turn a normal search box into a 500. Every
+ * bare `"` or a stray `*`/`NEAR`/`:` in user input can never raise FTS5's own
- * token is quoted (making it a literal phrase) and a trailing `*` is added to
+ * `fts5: syntax error` - that would turn a normal search into a 500.
- * the last token so typing continues to match as the user types.
+ */
+function quoteFtsTokens(raw: string): string[] {
+  return raw
+    .normalize('NFC')
+    .split(/[^\p{L}\p{N}_@.'-]+/u)
+    .map((t) => t.replace(/^['-]+|['-]+$/g, ''))
+    .filter((t) => t.length > 0)
+    .slice(0, 24)
+    .map((t, i, all) => {
+      const quoted = `"${t.replace(/"/g, '""')}"`;
+      // Prefix-match only the final token, and only if it's long enough to not
+      // match half the mailbox.
+      return i === all.length - 1 && t.length >= 3 ? `${quoted}*` : quoted;
+    });
+}
+
+/**
+ * Turns arbitrary user text into a safe FTS5 MATCH expression, every token
+ * required (AND-joined). Right for a deliberate, short search-box query,
+ * where requiring every word is what makes results precise as you type.
  *
  * Exported for unit testing - it is the one piece of this file with no
  * database dependency and the most ways to be wrong.
  */
 export function toFtsMatchQuery(raw: string): string | null {
   if (typeof raw !== 'string') return null;
-  // Split on anything that isn't a word character or an intra-word mark. Keeps
+  const tokens = quoteFtsTokens(raw);
-  // unicode letters (so "Müller" and "東京" survive) via the u flag.
-  const tokens = raw
-    .normalize('NFC')
-    .split(/[^\p{L}\p{N}_@.'-]+/u)
-    .map((t) => t.replace(/^['-]+|['-]+$/g, ''))
-    .filter((t) => t.length > 0)
-    .slice(0, 24);
   if (tokens.length === 0) return null;
-  return tokens
+  return tokens.join(' AND ');
-    .map((t, i) => {
+}
-      const quoted = `"${t.replace(/"/g, '""')}"`;
+
-      // Prefix-match only the final token, and only if it's long enough to not
+// A minimal, well-known set of English function words that carry no
-      // match half the mailbox.
+// retrieval signal - kept out of toFtsMatchQueryAny's OR expression so they
-      return i === tokens.length - 1 && t.length >= 3 ? `${quoted}*` : quoted;
+// don't drown out the bm25 ranking's actual signal (see below). Deliberately
-    })
+// NOT applied inside quoteFtsTokens/toFtsMatchQuery: that function's own
-    .join(' AND ');
+// tests rely on "AND"/"OR"/"NOT" surviving verbatim as literal search terms
+// (FTS5-keyword-injection safety) - a different concern from this one's job
+// of turning a natural-language QUESTION into a good search.
+const RETRIEVAL_STOP_WORDS = new Set([
+  'a', 'an', 'the', 'is', 'are', 'was', 'were', 'be', 'been', 'being', 'am',
+  'and', 'or', 'but', 'if', 'then', 'than', 'so', 'because',
+  'for', 'of', 'to', 'in', 'on', 'at', 'by', 'with', 'from', 'as', 'about', 'into', 'over', 'after', 'before',
+  'that', 'this', 'these', 'those', 'what', 'when', 'where', 'who', 'whom', 'which', 'why', 'how',
+  'do', 'does', 'did', 'doing', 'done',
+  'can', 'could', 'will', 'would', 'shall', 'should', 'may', 'might', 'must',
+  'i', 'you', 'he', 'she', 'it', 'we', 'they', 'my', 'your', 'his', 'her', 'its', 'our', 'their', 'me', 'him', 'us', 'them',
+  'not', 'no',
+]);
+
+/**
+ * Turns a natural-language QUESTION into a lenient FTS5 MATCH expression:
+ * stop words dropped, remaining tokens OR-joined so bm25 ranks by how many
+ * content words matched instead of requiring every one of them present.
+ *
+ * toFtsMatchQuery's strict AND is wrong for this shape of input: a real
+ * question like "When is check-in for the Villa sul Lago booking?" shares
+ * almost none of its own function words ("when"/"is"/"for"/"the") with the
+ * document that actually answers it, so ANDing every token together returns
+ * nothing - confirmed live: 0 hits for the full question, 2 correct hits for
+ * the same index once reduced to "Villa sul Lago check-in". The one real
+ * caller of `/api/offline/search?q=...` is exactly this AI-question shape
+ * (see that route's own header - no manual search-box UI hits it today), so
+ * this is the query builder that route now uses, not toFtsMatchQuery.
+ */
+export function toFtsMatchQueryAny(raw: string): string | null {
+  if (typeof raw !== 'string') return null;
+  const withoutStopWords = raw
+    .split(/\s+/)
+    .filter((w) => w.length > 0 && !RETRIEVAL_STOP_WORDS.has(w.toLowerCase().replace(/^[^\p{L}\p{N}]+|[^\p{L}\p{N}]+$/gu, '')))
+    .join(' ');
+  // Every word was a stop word (e.g. "What is this?") - fall back to the
+  // original text rather than searching for literally nothing.
+  const tokens = quoteFtsTokens(withoutStopWords.length > 0 ? withoutStopWords : raw);
+  if (tokens.length === 0) return null;
+  return tokens.join(' OR ');
 }

playwright.electron-ai.config.ts

@@ -0,0 +1,16 @@
+import { defineConfig } from '@playwright/test';
+
+// Separate from playwright.electron.config.ts (which hardcodes testMatch to
+// electron-smoke.spec.ts) purely so this one test can get a longer timeout —
+// real Ollama inference plus a real multi-round offline sync/reindex chain
+// legitimately takes longer than the smoke suite's 60s budget.
+export default defineConfig({
+  testDir: './e2e',
+  testMatch: 'electron-ai-local-index.spec.ts',
+  timeout: 120000,
+  retries: 0,
+  use: {
+    trace: 'retain-on-failure',
+  },
+  workers: 1,
+});