fix(connectors): index Google Chat spaces with no messages in the window

Review round 1.

- orderBy takes a full ordering expression, not a bare direction. The reference
  documents the default as `createTime ASC`, so send `createTime DESC`; a bare
  `DESC` either 400s every hydration or is ignored, which would make the cap keep
  the oldest traffic and the later reverse render the transcript backwards.
- getDocument no longer returns null when the message window is empty. A space
  with no messages is still a live space, and null is the "document is gone"
  signal the engine treats as last-known-good: returning it dropped spaces whose
  only prose is their description or guidelines, and left a stale transcript
  indexed after a space was cleared or lookbackDays was tightened past every
  message.
- The transcript header is omitted when no message contributed text.

apps/sim/connectors/google-chat/google-chat.test.ts

@@ -44,20 +44,26 @@ const fetchMock = vi.fn<(input: string | URL | Request, init?: RequestInit) => P
 let listedSpaces: Record<string, unknown>[] = [SPACE]
 /** `nextPageToken` returned by `spaces.list`; per-test overridable. */
 let listNextPageToken: string | undefined
+/** Messages returned by `spaces.messages.list`; per-test overridable. */
+let listedMessages: Record<string, unknown>[] = MESSAGES
+/** Space returned by `spaces.list` / `spaces.get`; per-test overridable. */
+let fetchedSpace: Record<string, unknown> = SPACE
 
 beforeEach(() => {
   requestedUrls.length = 0
   listedSpaces = [SPACE]
   listNextPageToken = undefined
+  listedMessages = MESSAGES
+  fetchedSpace = SPACE
   fetchMock.mockReset()
   fetchMock.mockImplementation(async (input) => {
     const url = String(input)
     requestedUrls.push(url)
-    if (url.includes('/messages?')) return jsonResponse({ messages: MESSAGES })
+    if (url.includes('/messages?')) return jsonResponse({ messages: listedMessages })
     if (url.includes('/spaces?')) {
       return jsonResponse({ spaces: listedSpaces, nextPageToken: listNextPageToken })
     }
-    if (url.endsWith(`/${SPACE_NAME}`)) return jsonResponse(SPACE)
+    if (url.endsWith(`/${SPACE_NAME}`)) return jsonResponse(fetchedSpace)
     return jsonResponse({ error: { message: 'not found' } }, 404)
   })
   vi.stubGlobal('fetch', fetchMock)
@@ -204,10 +210,50 @@ describe('google-chat listing caps', () => {
   })
 })
 
+describe('google-chat empty windows', () => {
+  it('indexes a space whose only prose is its description when no message has text', async () => {
+    fetchedSpace = { ...SPACE, spaceDetails: { description: 'Release coordination' } }
+    listedSpaces = [fetchedSpace]
+    listedMessages = []
+
+    const doc = await googleChatConnector.getDocument('token', {}, SPACE_NAME)
+    expect(doc).not.toBeNull()
+    expect(doc?.content).toContain('Release coordination')
+  })
+
+  it('indexes a space whose only prose is its guidelines when no message has text', async () => {
+    fetchedSpace = { ...SPACE, spaceDetails: { guidelines: 'Be excellent to each other' } }
+    listedSpaces = [fetchedSpace]
+    listedMessages = []
+
+    const doc = await googleChatConnector.getDocument('token', {}, SPACE_NAME)
+    expect(doc?.content).toContain('Be excellent to each other')
+  })
+
+  it('returns a document rather than null when the window is empty, so a cleared space does not keep a stale transcript', async () => {
+    listedMessages = []
+    const doc = await googleChatConnector.getDocument('token', {}, SPACE_NAME)
+    expect(doc).not.toBeNull()
+    expect(doc?.content).not.toContain('Shipping today')
+    expect(doc?.metadata?.messageCount).toBe(0)
+  })
+
+  it('omits the transcript header entirely when no message contributed text', async () => {
+    listedMessages = []
+    const doc = await googleChatConnector.getDocument('token', {}, SPACE_NAME)
+    expect(doc?.content).not.toContain('--- Messages ---')
+  })
+
+  it('still returns null when the space itself is gone', async () => {
+    const doc = await googleChatConnector.getDocument('token', {}, 'spaces/MISSING')
+    expect(doc).toBeNull()
+  })
+})
+
 describe('google-chat message window', () => {
   it('requests messages newest-first so the cap keeps the most recent conversation', async () => {
     await googleChatConnector.getDocument('token', {}, SPACE_NAME)
-    expect(messagesParams().get('orderBy')).toBe('DESC')
+    expect(messagesParams().get('orderBy')).toBe('createTime DESC')
   })
 
   it('renders the newest-first page back into chronological order', async () => {

apps/sim/connectors/google-chat/google-chat.ts

@@ -256,8 +256,12 @@ function rfc3339(date: Date): string {
 
 /**
  * Fetches the newest `maxMessages` messages of a space, optionally bounded by a
- * lookback window. Messages are requested newest-first (`orderBy=DESC`) so the
- * cap keeps the most recent conversation, then returned in chronological order.
+ * lookback window. Messages are requested newest-first so the cap keeps the most
+ * recent conversation, then returned in chronological order.
+ *
+ * `orderBy` takes a full ordering expression, not a bare direction: the reference
+ * documents the default as `createTime ASC` and lists ASC/DESC as the ordering
+ * *operations* usable within one. `createTime` is the only orderable field here.
  */
 async function fetchSpaceMessages(
   accessToken: string,
@@ -276,7 +280,7 @@ async function fetchSpaceMessages(
   while (collected.length < maxMessages) {
     const params = new URLSearchParams({
       pageSize: String(Math.min(MESSAGES_PAGE_SIZE, maxMessages - collected.length)),
-      orderBy: 'DESC',
+      orderBy: 'createTime DESC',
     })
     if (filter) params.set('filter', filter)
     if (pageToken) params.set('pageToken', pageToken)
@@ -326,14 +330,18 @@ function formatSpaceContent(space: Space, messages: ChatMessage[]): string {
   const guidelines = space.spaceDetails?.guidelines?.trim()
   if (guidelines) parts.push(`Guidelines: ${guidelines}`)
 
-  parts.push('')
-  parts.push('--- Messages ---')
-
+  const lines: string[] = []
   for (const message of messages) {
     const text = message.text?.trim() || message.fallbackText?.trim()
     if (!text) continue
     const timestamp = message.createTime ?? ''
-    parts.push(`[${timestamp}] ${senderLabel(message.sender)}: ${text}`)
+    lines.push(`[${timestamp}] ${senderLabel(message.sender)}: ${text}`)
+  }
+
+  if (lines.length > 0) {
+    parts.push('')
+    parts.push('--- Messages ---')
+    parts.push(...lines)
   }
 
   return parts.join('\n')
@@ -460,12 +468,15 @@ export const googleChatConnector: ConnectorConfig = {
     const lookbackDays = resolveLookbackDays(sourceConfig.lookbackDays)
     const messages = await fetchSpaceMessages(accessToken, spaceName, maxMessages, lookbackDays)
 
+    /**
+     * A space with no messages in the window is still a live space, so it is
+     * indexed rather than skipped. `null` is this connector's "document is gone"
+     * signal, and the engine treats it as last-known-good: returning it here would
+     * both drop spaces whose only prose is their description or guidelines, and
+     * leave a previously indexed transcript in place after the space was cleared
+     * or `lookbackDays` was tightened past every message.
+     */
     const messageCount = countIndexedMessages(messages)
-    if (messageCount === 0) {
-      logger.info('No indexable messages in Google Chat space', { externalId })
-      return null
-    }
-
     const stub = spaceToStub(space, maxMessages, lookbackDays, syncContext)
 
     return {