Make new_suggestions and Send to Google Chat recoverable

MQ-167-01: a scheduled or manual batch now emits new_suggestions:{batchId}
in the transaction that first stores its Side quests, so the cards and
their notification commit together. A later round that fails, or a
failure recording the batch's end, no longer loses the event; a later
round's emit is a no-op by key; a notification that cannot be stored
fails that store, leaving no unannounced cards. Replenish batches still
never notify. finishBatch goes back to recording status only.

MQ-167-02: migration 0017 adds shopping_lists.chat_send_unconfirmed_at.
SendToChat records the send as begun before posting, clears it with
sent_to_chat_at once Google Chat accepts, and clears it alone when Chat
refuses. A post Chat does not answer, or one it accepts that cannot be
recorded, is ErrSendUnconfirmed (502 chat_unconfirmed, not retryable)
and leaves the marker, as does a crash mid-send; a repeat without resend
never reposts, and resend posts again. The Supply run screen re-reads
the list after a failed send, shows an unconfirmed send, offers no Retry
for it, and sends again only with resend.

Task: f0cd9d50-9c11-41be-a945-7bae9f5f28a4

Co-Authored-By: Claude Opus 5.5 <noreply@anthropic.com>

web/src/App.test.tsx

@@ -120,6 +120,7 @@ describe('App routes', () => {
           title: null,
           status: 'current',
           sent_to_chat_at: null,
+          chat_send_unconfirmed_at: null,
           needed_count: 1,
           total_count: 1,
           groups: [{ dinner: { id: 'd1', name: 'Beef tacos' }, date: week, day: 'Monday', items: [{ id: 'i1', name: 'Ground beef', qty: '1 lb', needed: true }] }],

web/src/plan/PlanPage.test.tsx

@@ -215,6 +215,7 @@ function supplyRun(needed: number) {
     title: null,
     status: 'current',
     sent_to_chat_at: null,
+    chat_send_unconfirmed_at: null,
     needed_count: needed,
     total_count: 32,
     groups: [],

web/src/shopping/SupplyArchivePage.test.tsx

@@ -308,6 +308,7 @@ const FROZEN = {
   title: 'Pizza, pot roast & the great orzo trial',
   status: 'archived',
   sent_to_chat_at: null,
+  chat_send_unconfirmed_at: null,
   needed_count: 1,
   total_count: 2,
   groups: [

web/src/shopping/SupplyRunPage.module.css

@@ -238,6 +238,10 @@
   color: var(--color-accent-2-800);
 }
 
+.unconfirmed {
+  color: var(--color-accent-700);
+}
+
 .footer {
   display: flex;
   flex-direction: column;

web/src/shopping/SupplyRunPage.test.tsx

@@ -53,6 +53,7 @@ function supplyRun(overrides: Record<string, unknown> = {}, weekStart = '2026-10
     title: null,
     status: 'current',
     sent_to_chat_at: null,
+    chat_send_unconfirmed_at: null,
     needed_count: items.filter((item) => item.needed).length,
     total_count: items.length,
     groups: GROUPS,
@@ -446,6 +447,49 @@ describe('SupplyRunPage', () => {
     expect(writes(fetchMock)).toEqual([`POST ${SEND_CHAT} {"resend":false}`, `POST ${SEND_CHAT} {"resend":false}`])
   })
 
+  it('says a send whose outcome is not known was not confirmed, offers no retry, and sends again only with resend', async () => {
+    mockViewport(1180)
+    let run = supplyRun()
+    const answers = [
+      () => {
+        // Saturday Oct 10, 8:00 am in New York.
+        run = supplyRun({ chat_send_unconfirmed_at: '2026-10-10T12:00:00Z' })
+        return errorResponse(502, 'chat_unconfirmed')
+      },
+      () => jsonResponse(200, supplyRun({ sent_to_chat_at: '2026-10-10T12:05:00Z' })),
+    ]
+    const fetchMock = stubServer({
+      [`GET ${THIS_WEEK}`]: () => jsonResponse(200, run),
+      [`POST ${SEND_CHAT}`]: () => answers.shift()!(),
+    })
+    await renderPage()
+
+    fireEvent.click(await screen.findByRole('button', { name: 'Send to Google Chat' }))
+
+    const alert = await screen.findByRole('alert')
+    expect(alert).toHaveTextContent("Couldn't send the shopping list to Google Chat. chat_unconfirmed message")
+    expect(within(alert).queryByRole('button')).not.toBeInTheDocument()
+    // The Supply run is read again, and says the send is unconfirmed.
+    expect(
+      await screen.findByText('Send to Google Chat not confirmed · Sat 8:00 am — check the space before sending again'),
+    ).toBeInTheDocument()
+    expect(screen.queryByText(/Sent to Google Chat ·/)).not.toBeInTheDocument()
+
+    fireEvent.click(screen.getByRole('button', { name: 'Send again' }))
+    expect(await screen.findByText('Sent to Google Chat · Sat 8:05 am')).toBeInTheDocument()
+    expect(screen.queryByText(/not confirmed/)).not.toBeInTheDocument()
+    expect(writes(fetchMock)).toEqual([`POST ${SEND_CHAT} {"resend":false}`, `POST ${SEND_CHAT} {"resend":true}`])
+  })
+
+  it('shows an unconfirmed send on mobile', async () => {
+    stubServer({ [`GET ${THIS_WEEK}`]: () => jsonResponse(200, supplyRun({ chat_send_unconfirmed_at: '2026-10-10T12:00:00Z' })) })
+    await renderPage()
+
+    expect(
+      await screen.findByText('Send to Google Chat not confirmed · Sat 8:00 am — check the space before sending again'),
+    ).toBeInTheDocument()
+  })
+
   it('renders an archived list read-only, tagged Archived', async () => {
     const fetchMock = stubServer({
       'GET /api/v1/shopping/2026-09-28': () =>

web/src/shopping/SupplyRunPage.tsx

@@ -2,6 +2,7 @@ import { Archive, Check, CloudUpload, MessageSquare } from 'lucide-react'
 import { useState } from 'react'
 import { Link, useSearchParams } from 'react-router'
 import { defaultWeek, localNow, weekdayKicker, weekLabel, weekStart as weekOf } from '../plan/week.ts'
+import { ApiError } from '../api/errors.ts'
 import { formatClockTime, useHouseholdSettings } from '../settings/api.ts'
 import { useBreakpoint, type Breakpoint } from '../shell/useBreakpoint.ts'
 import { Button } from '../ui/Button.tsx'
@@ -101,8 +102,20 @@ function SentStatus({ at, timezone }: { at: Date; timezone: string }) {
   )
 }
 
+// UnconfirmedStatus is the status line while a send to Google Chat whose
+// outcome is not known is recorded: it may or may not have been posted.
+function UnconfirmedStatus({ at, timezone }: { at: Date; timezone: string }) {
+  return (
+    <p className={`${styles.sent} ${styles.unconfirmed}`}>
+      <Icon icon={MessageSquare} size="inline" />
+      Send to Google Chat not confirmed · {sentAt(at, timezone)} — check the space before sending again
+    </p>
+  )
+}
+
 // SendToChat posts the Supply run to Google Chat: "Send to Google Chat"
-// until it is sent, then "Send again", which posts it once more.
+// until it is sent, or a send is unconfirmed, then "Send again", which
+// posts it once more.
 function SendToChat({ sent, pending, onSend }: { sent: boolean; pending: boolean; onSend: () => void }) {
   return (
     <Button className={styles.action} disabled={pending} onClick={onSend}>
@@ -128,7 +141,8 @@ function ArchiveLink({ layout }: { layout: Breakpoint }) {
 // the week's dates, the title with the count still to buy of all items, and
 // one card per dinner, stacked on mobile and in three masonry columns from
 // tablet up, where Archive and Send to Google Chat are actions in the
-// header; a send that fails says why. On a current Supply run each item toggles at once (useToggles); a
+// header; a send that fails says why, and one whose outcome is not known
+// offers no retry and leaves the status line saying so. On a current Supply run each item toggles at once (useToggles); a
 // toggle refused puts the item back and says why. An archived one, or any
 // opened from the Supply archive (readOnly), is read-only and tagged
 // Archived, and a toggle it refused is not offered again.
@@ -137,6 +151,12 @@ function SupplyRunList({ weekStart, timezone, layout, readOnly }: WeekProps) {
   const send = useSendToChat(weekStart)
   const run = toggles.shown
   const sent = run.sent_to_chat_at !== null
+  // A send whose outcome is not known is posted again only on request.
+  const resend = sent || run.chat_send_unconfirmed_at !== null
+  const unconfirmed = !send.isPending && run.chat_send_unconfirmed_at !== null && (
+    <UnconfirmedStatus at={run.chat_send_unconfirmed_at} timezone={timezone} />
+  )
+  const sendUnconfirmed = send.error instanceof ApiError && send.error.code === 'chat_unconfirmed'
   const viewOnly = readOnly || run.status === 'archived'
   const wide = layout !== 'mobile'
   const failed = toggles.failed
@@ -165,7 +185,7 @@ function SupplyRunList({ weekStart, timezone, layout, readOnly }: WeekProps) {
         {wide && (
           <div className={styles.actions}>
             <ArchiveLink layout={layout} />
-            {!viewOnly && <SendToChat sent={sent} pending={send.isPending} onSend={() => send.mutate(sent)} />}
+            {!viewOnly && <SendToChat sent={resend} pending={send.isPending} onSend={() => send.mutate(resend)} />}
           </div>
         )}
       </header>
@@ -176,9 +196,12 @@ function SupplyRunList({ weekStart, timezone, layout, readOnly }: WeekProps) {
         </ErrorBanner>
       )}
       {send.isError && !viewOnly && (
-        <ErrorBanner onRetry={() => send.mutate(sent)}>Couldn't send the shopping list to Google Chat. {send.error.message}</ErrorBanner>
+        <ErrorBanner onRetry={sendUnconfirmed ? undefined : () => send.mutate(resend)}>
+          Couldn't send the shopping list to Google Chat. {send.error.message}
+        </ErrorBanner>
       )}
       {wide && run.sent_to_chat_at !== null && <SentStatus at={run.sent_to_chat_at} timezone={timezone} />}
+      {wide && unconfirmed}
       {run.groups.length === 0 ? (
         <EmptyState title="Nothing to buy">None of this week's dinners has a recipe with ingredients yet.</EmptyState>
       ) : (
@@ -191,6 +214,7 @@ function SupplyRunList({ weekStart, timezone, layout, readOnly }: WeekProps) {
       {!wide && (
         <footer className={styles.footer}>
           {run.sent_to_chat_at !== null && <SentStatus at={run.sent_to_chat_at} timezone={timezone} />}
+          {unconfirmed}
           <ArchiveLink layout={layout} />
         </footer>
       )}

web/src/shopping/api.ts

@@ -72,14 +72,17 @@ export type SupplyRunGroup = { dinner: { id: string; name: string }; date: strin
 export type Counts = { needed_count: number; total_count: number }
 
 // SupplyRun is GET /api/v1/shopping/{weekStart}: label is the week label,
-// "Week 41 · Oct 5 – 11", title the AI's title once written, and
-// sent_to_chat_at when it was sent to Google Chat, if it was.
+// "Week 41 · Oct 5 – 11", title the AI's title once written,
+// sent_to_chat_at when it was sent to Google Chat, if it was, and
+// chat_send_unconfirmed_at when a send whose outcome is not known began,
+// if one did: it may or may not have reached Google Chat.
 export type SupplyRun = Counts & {
   weekStart: string
   label: string
   title: string | null
   status: SupplyRunStatus
   sent_to_chat_at: Date | null
+  chat_send_unconfirmed_at: Date | null
   groups: SupplyRunGroup[]
 }
 
@@ -125,12 +128,12 @@ function parseGroup(where: string, body: unknown): SupplyRunGroup {
   }
 }
 
-// sentAt reads sent_to_chat_at, an RFC 3339 instant or null.
-function sentAt(where: string, value: unknown): Date | null {
+// instant reads field, an RFC 3339 instant or null.
+function instant(where: string, field: string, value: unknown): Date | null {
   if (value === null) return null
   const at = typeof value === 'string' ? new Date(value) : null
   if (at === null || Number.isNaN(at.getTime())) {
-    throw new Error(`${where}: sent_to_chat_at ${JSON.stringify(value)} is not an instant`)
+    throw new Error(`${where}: ${field} ${JSON.stringify(value)} is not an instant`)
   }
   return at
 }
@@ -150,7 +153,8 @@ export function parseSupplyRun(where: string, weekStart: string, body: unknown):
     label: body.label,
     title: body.title,
     status: oneOf(where, 'status', SUPPLY_RUN_STATUSES, body.status),
-    sent_to_chat_at: sentAt(where, body.sent_to_chat_at),
+    sent_to_chat_at: instant(where, 'sent_to_chat_at', body.sent_to_chat_at),
+    chat_send_unconfirmed_at: instant(where, 'chat_send_unconfirmed_at', body.chat_send_unconfirmed_at),
     ...parseCounts(where, body),
     groups: body.groups.map((group) => parseGroup(where, group)),
   }
@@ -208,9 +212,10 @@ export function useGenerateSupplyRun(weekStart: string) {
 
 // useSendToChat posts the week's Supply run to Google Chat (POST
 // /api/v1/shopping/{weekStart}/send-chat); the Supply run it answers with,
-// sent_to_chat_at recorded, is the one shown. A week already sent is posted
-// again only with resend: without it the server answers with the Supply
-// run as it is.
+// sent_to_chat_at recorded, is the one shown. A week already sent, or with
+// a send unconfirmed, is posted again only with resend: without it the
+// server answers with the Supply run as it is. A send that fails re-reads
+// the Supply run, so a send left unconfirmed shows as such.
 export function useSendToChat(weekStart: string) {
   const { apiFetch } = useApi()
   const queryClient = useQueryClient()
@@ -222,6 +227,7 @@ export function useSendToChat(weekStart: string) {
     onSuccess: (run) => {
       queryClient.setQueryData<SupplyRun | null>(supplyRunKey(weekStart), run)
     },
+    onError: () => queryClient.invalidateQueries({ queryKey: supplyRunKey(weekStart) }),
   })
 }
 

web/src/shopping/offlineQueue.test.tsx

@@ -93,6 +93,7 @@ function stubServer(
     title: null,
     status: week === '2026-10-05' ? status : 'current',
     sent_to_chat_at: null,
+    chat_send_unconfirmed_at: null,
     ...counts(week),
     groups: [
       {