Wire plan_ready, list_ready, new_suggestions and Send to Google Chat (Feature 19) (#167)

Co-authored-by: orchestrator-agent <20+orchestrator-agent@code.cubecraftcreations.com>

cmd/server/main.go

@@ -109,11 +109,30 @@ func run(cfg config.Config, logger *slog.Logger) error {
 	if err != nil {
 		return err
 	}
+	notifier, err := notify.NewService(db, logger)
+	if err != nil {
+		return err
+	}
+	pushSender, err := push.NewSender(db, logger, cfg.VAPID.PublicKey, cfg.VAPID.PrivateKey.Reveal(), cfg.VAPID.Subject)
+	if err != nil {
+		return err
+	}
+	if err := notifier.Register(notify.ChannelPush, pushSender); err != nil {
+		return err
+	}
+	chatSvc, err := chat.NewService(db, box, cfg.PublicURL, http.DefaultTransport)
+	if err != nil {
+		return err
+	}
+	if err := notifier.Register(notify.ChannelChat, chatSvc); err != nil {
+		return err
+	}
+
 	dinnerSvc, err := dinners.NewService(db, grounder, runner, logger)
 	if err != nil {
 		return err
 	}
-	suggestSvc, err := suggest.NewService(db, grounder, sideQuests(ai, guard), runner, logger)
+	suggestSvc, err := suggest.NewService(db, grounder, sideQuests(ai, guard), runner, notifier, logger)
 	if err != nil {
 		return err
 	}
@@ -131,12 +150,12 @@ func run(cfg config.Config, logger *slog.Logger) error {
 		return err
 	}
 
-	planSvc, err := plan.NewService(db, weekDrafter(ai, guard), runner, googleSvc, cfg.PublicURL, logger)
+	planSvc, err := plan.NewService(db, weekDrafter(ai, guard), runner, googleSvc, notifier, cfg.PublicURL, logger)
 	if err != nil {
 		return err
 	}
 
-	shopSvc, err := shopping.NewService(db, archiveTitler(ai, guard), runner, logger)
+	shopSvc, err := shopping.NewService(db, archiveTitler(ai, guard), runner, notifier, chatSvc, logger)
 	if err != nil {
 		return err
 	}
@@ -146,25 +165,6 @@ func run(cfg config.Config, logger *slog.Logger) error {
 		return err
 	}
 
-	notifier, err := notify.NewService(db, logger)
-	if err != nil {
-		return err
-	}
-	pushSender, err := push.NewSender(db, logger, cfg.VAPID.PublicKey, cfg.VAPID.PrivateKey.Reveal(), cfg.VAPID.Subject)
-	if err != nil {
-		return err
-	}
-	if err := notifier.Register(notify.ChannelPush, pushSender); err != nil {
-		return err
-	}
-	chatSvc, err := chat.NewService(db, box, cfg.PublicURL, http.DefaultTransport)
-	if err != nil {
-		return err
-	}
-	if err := notifier.Register(notify.ChannelChat, chatSvc); err != nil {
-		return err
-	}
-
 	sessions, err := auth.NewSessionManager(db, cfg.SessionIdle, cfg.SessionMax)
 	if err != nil {
 		return err

docs/ARCHITECTURE.md

@@ -104,7 +104,7 @@ Columns ending in `_ct` hold AES-256-GCM ciphertext (via `secretbox`).
 | `week_plans` | week_start (unique), status (`draft` / `synced` / `changed`), ai_note, ai_run_id, calendar_synced_at, revision (raised by every swap and stored draft). |
 | `plan_days` | plan_id, date (unique per plan), dinner_id, is_new, calendar_event_id (set while the chosen calendar shows the day as planned; cleared when its dinner changes, another calendar is chosen or Google Calendar is disconnected). |
 | `rotation_reviews` | dinner_id + plan_date (unique), status, decision (`keep` / `drop` / `not_made`), name (set only by a drop: the dinner's name when dropped, kept whatever it is later renamed, so a drop stays among the passed names), decided_at, updated_by. |
-| `shopping_lists` | week_start (unique), plan_id, title (the AI-written post title; NULL until written or when the AI fails, when the week label is shown instead; never empty), status (`current` / `archived`), sent_to_chat_at, frozen_at. |
+| `shopping_lists` | week_start (unique), plan_id, title (the AI-written post title; NULL until written or when the AI fails, when the week label is shown instead; never empty), status (`current` / `archived`), sent_to_chat_at, chat_send_unconfirmed_at (a send to Google Chat recorded as begun before posting and cleared once its outcome is known; left set when it may or may not have posted), frozen_at. |
 | `shopping_groups` / `shopping_items` | One group per plan day with ingredients: dinner_id, date, position (by date). Item name, qty (the display quantity, NULL when the recipe gives none), needed (bool), position. Made by `shopping.Generate` from the plan, with no model call: an item is a grounded recipe ingredient's normalized name with qty and unit joined ("2 cups"), or a manual recipe's line as typed with no qty. Regenerating keeps the id and needed flag of an item whose (dinner_id, name) is unchanged. |
 | `ai_settings` | One row: provider, base_url, model, temperature, system_prompt, api_key_ct, api_key_last4, key_verified_at. |
 | `recipe_search_settings` | One row: provider (`searxng` / `brave`), base_url (the SearXNG instance), api_key_ct and api_key_last4 (Brave). |
@@ -656,6 +656,28 @@ Runs are recorded in `schedule_runs` and executed through `jobs`.
 - Events: `plan_ready`, `list_ready`, `day_of_reminder`, `new_suggestions`,
   `rotation_review`; each can go to Web Push and/or Google Chat per
   `notification_prefs`.
+- Where each event is emitted, with its idempotency key. Each is stored by
+  `notify.EmitTx` in the transaction of the change it is about, so the
+  change and its notification commit together or not at all:
+  - `plan_ready:{weekStart}` (URL `/plan`) when a draft job stores the
+    AI's draft of a week. Only the first draft of a week notifies: a
+    redraft (Rebuild week) has the same key, and a manual swap never
+    drafts. Its title is "Next week's plan is ready" (or "This week's",
+    or "The plan for the week of Oct 26") and its body the drafted
+    dinners Monday to Sunday.
+  - `list_ready:{weekStart}` (URL `/plan/shopping`) when a week's Supply
+    run is first created, by `POST /shopping/{weekStart}/generate` or
+    after Push to Calendar; remaking it does not notify.
+  - `new_suggestions:{batchId}` (URL `/discover`) when a `scheduled` or
+    `manual` suggestion batch first adds Side quests to the deck, in the
+    transaction storing them, so they are announced even when a later
+    round or recording the batch's end fails; it names that round's Side
+    quests, and a later round's emit stores nothing. A `replenish` batch
+    never notifies.
+  - `day_of_reminder:{date}` (URL `/dinner/{id}`) through
+    `plan.Service.EmitDayOfReminder(date)`, which names the dinner planned
+    on the date and emits nothing for a week with no plan. The scheduler
+    calls it at `reminder_time` (Feature 20).
 - Delivery goes through `notification_outbox`.
 - Web Push uses VAPID (`webpush-go`). Google Chat uses the stored incoming
   webhook.
@@ -870,7 +892,8 @@ Runs are recorded in `schedule_runs` and executed through `jobs`.
 ## Supply run API (Feature 17)
 
 - `GET /api/v1/shopping/{weekStart}` returns `{weekStart, label, title,
-  status, sent_to_chat_at, needed_count, total_count, groups: [{dinner:
+  status, sent_to_chat_at, chat_send_unconfirmed_at, needed_count,
+  total_count, groups: [{dinner:
   {id, name}, date, day, items: [{id, name, qty, needed}]}]}`: `label` is
   the week label (shown while `title` is null), `day` the plan day's
   weekday ("Monday"), `qty` null when the recipe gives none,
@@ -880,6 +903,27 @@ Runs are recorded in `schedule_runs` and executed through `jobs`.
   through `shopping.Generate` and answers with the same shape plus
   `skipped: [{date, dinner_id, dinner_name, reason}]`. 404 when the week
   has no plan, 409 `archived` when its list is in the Supply archive.
+- `POST /api/v1/shopping/{weekStart}/send-chat` (CSRF-checked) takes
+  `{}` or `{"resend": true}` and posts the Supply run to Google Chat
+  through `chat.PostSupplyRun`, in the week's thread: "Supply run · " and
+  its title (or week label), each dinner with items still needed and those
+  items, and a card whose "Open" button links to
+  `/plan/shopping?week={weekStart}` under `MEALQUEST_PUBLIC_URL`. It
+  records `chat_send_unconfirmed_at` before posting, then
+  `sent_to_chat_at` (clearing it) once Google Chat accepts, and answers
+  with the Supply run as `GET` gives it. A week already sent, or with a
+  send unconfirmed, is answered as it is, with no second post, unless
+  `resend` is true. No webhook stored is 409 `not_configured`; Google Chat
+  answering with a status other than 2xx is 502 `chat_refused` (retryable
+  only for 429 or 5xx), clearing the send begun; Google Chat not
+  answering, or accepting a post that cannot then be recorded, is 502
+  `chat_unconfirmed` (not retryable: the post may have been made), which
+  leaves `chat_send_unconfirmed_at` set, as does the process stopping
+  mid-send. The screen shows an unconfirmed send and sends again only on
+  request. 404 when the week has no Supply run, 409
+  `archived` when it is in the Supply archive, 400 `invalid_request` for a
+  bad body. `shopping.SendToChat(weekStart, resend)` is what
+  `shopping_chat_autosend` calls (Feature 20).
 - `PATCH /api/v1/shopping/items/{id}` takes `{needed}` (a required
   boolean; it sets the flag, it does not flip it) and answers `{id,
   needed, needed_count, total_count}` with the list's counts after the

internal/chat/chat.go

@@ -53,6 +53,9 @@ var (
 	// ErrUnreachable is wrapped by the error of a post Google Chat did not
 	// answer.
 	ErrUnreachable = errors.New("chat: Google Chat did not answer")
+	// ErrRefused is matched by the *RefusedError of a post Google Chat
+	// answered with a status other than 2xx.
+	ErrRefused = errors.New("chat: Google Chat refused the message")
 	// ErrWebhookChanged is returned by Test when the webhook was replaced
 	// while the test message was being sent; nothing is recorded.
 	ErrWebhookChanged = errors.New("chat: the Google Chat webhook changed during the test")
@@ -78,6 +81,24 @@ type TestResult struct {
 	Settings
 }
 
+// RefusedError is a post Google Chat answered with Status, not 2xx. It
+// matches ErrRefused.
+type RefusedError struct {
+	Status int
+}
+
+func (e *RefusedError) Error() string {
+	return fmt.Sprintf("%v with status %d", ErrRefused, e.Status)
+}
+
+func (e *RefusedError) Unwrap() error { return ErrRefused }
+
+// Retryable reports whether posting again may succeed: Google Chat was
+// busy (429) or failing (5xx), rather than refusing the message.
+func (e *RefusedError) Retryable() bool {
+	return e.Status == http.StatusTooManyRequests || e.Status >= 500
+}
+
 // Problem is one invalid field of a webhook update, named by its JSON key.
 type Problem struct {
 	Field  string
@@ -362,22 +383,65 @@ func (s *Service) messageOf(p notify.Payload) (message, error) {
 	if !carded[p.Event] {
 		return msg, nil
 	}
-	ref, err := url.Parse(p.URL)
-	if err != nil || ref.Scheme != "" || ref.Host != "" || !strings.HasPrefix(p.URL, "/") {
-		return message{}, fmt.Errorf("payload url %q is not an app path", p.URL)
+	c, err := s.openCard(string(p.Event), p.Title, p.Body, p.URL)
+	if err != nil {
+		return message{}, err
+	}
+	msg.CardsV2 = []cardV2{c}
+	return msg, nil
+}
+
+// openCard is a card headed title and subtitle whose "Open" button links
+// to the app path under the public URL.
+func (s *Service) openCard(id, title, subtitle, path string) (cardV2, error) {
+	ref, err := url.Parse(path)
+	if err != nil || ref.Scheme != "" || ref.Host != "" || !strings.HasPrefix(path, "/") {
+		return cardV2{}, fmt.Errorf("payload url %q is not an app path", path)
 	}
 	link := s.publicURL.ResolveReference(ref)
-	msg.CardsV2 = []cardV2{{
-		CardID: string(p.Event),
+	return cardV2{
+		CardID: id,
 		Card: card{
-			Header: cardHeader{Title: p.Title, Subtitle: p.Body},
+			Header: cardHeader{Title: title, Subtitle: subtitle},
 			Sections: []cardSection{{Widgets: []cardWidget{{ButtonList: buttonList{Buttons: []button{{
 				Text:    "Open",
 				OnClick: onClick{OpenLink: openLink{URL: link.String()}},
 			}}}}}}},
 		},
-	}}
-	return msg, nil
+	}, nil
+}
+
+// PostSupplyRun posts the Supply run of the week starting on week, named
+// name, with groups, to the stored webhook in the week's thread: its
+// SupplyRunText and a card whose "Open" button links to that week's Supply
+// run. No webhook stored is ErrNotConfigured; a post Google Chat does not
+// answer wraps ErrUnreachable, and one it answers with a status other than
+// 2xx is a *RefusedError.
+func (s *Service) PostSupplyRun(ctx context.Context, week store.LocalDate, name string, groups []SupplyRunGroup) error {
+	row, err := db.New(s.st.Reader).GetChatSettings(ctx)
+	if errors.Is(err, sql.ErrNoRows) {
+		return ErrNotConfigured
+	}
+	if err != nil {
+		return fmt.Errorf("chat: read chat settings: %w", err)
+	}
+	hook, err := s.open(row)
+	if err != nil {
+		return err
+	}
+	path := "/plan/shopping?" + url.Values{"week": {week.String()}}.Encode()
+	c, err := s.openCard("supply_run", "Supply run · "+name, "", path)
+	if err != nil {
+		return err
+	}
+	status, err := s.post(ctx, hook, message{Text: SupplyRunText(name, groups), CardsV2: []cardV2{c}}, ThreadKey(week))
+	if err != nil {
+		return err
+	}
+	if status < 200 || status >= 300 {
+		return &RefusedError{Status: status}
+	}
+	return nil
 }
 
 // post sends msg to hook, in thread when it is not empty, and returns the

internal/chat/chat_test.go

@@ -304,7 +304,7 @@ func TestSendThreadsByWeek(t *testing.T) {
 	}
 	week := mustDate(t, "2026-10-12")
 	events := []notify.Event{
-		PlanReady(week, []string{"Tacos", "Bolognese", "Tikka masala", "A", "B", "C", "D"}),
+		PlanReady(week, week, []string{"Tacos", "Bolognese", "Tikka masala", "A", "B", "C", "D"}),
 		ListReady(week, 19, 7),
 		DayOfReminder(mustDate(t, "2026-10-18"), "01J9DINNER", "Tacos"),
 		NewSuggestions("01J9BATCH", week, []string{"Pho"}),
@@ -383,7 +383,7 @@ func TestSendClassifiesStatus(t *testing.T) {
 	if _, err := svc.Put(ctx, testHook, "Family"); err != nil {
 		t.Fatal(err)
 	}
-	m := notify.Message{Payload: payloadOf(PlanReady(mustDate(t, "2026-10-12"), []string{"Tacos"}))}
+	m := notify.Message{Payload: payloadOf(PlanReady(mustDate(t, "2026-10-12"), mustDate(t, "2026-10-12"), []string{"Tacos"}))}
 	for _, tc := range []struct {
 		status        int
 		ok, permanent bool
@@ -464,7 +464,7 @@ func TestOutboxRowsFollowClassification(t *testing.T) {
 
 	week := mustDate(t, "2026-10-12")
 	f.setStatus(http.StatusBadRequest)
-	planned := PlanReady(week, []string{"Tacos"})
+	planned := PlanReady(week, week, []string{"Tacos"})
 	if err := notifier.Emit(ctx, planned); err != nil {
 		t.Fatal(err)
 	}
@@ -528,3 +528,61 @@ func (b *syncBuffer) String() string {
 	defer b.mu.Unlock()
 	return b.buf.String()
 }
+
+func TestPostSupplyRun(t *testing.T) {
+	t.Parallel()
+	ctx := context.Background()
+	f := newFakeChat(t)
+	svc, _ := newTestService(t, f)
+	week := mustDate(t, "2026-10-12")
+	groups := []SupplyRunGroup{{Dinner: "Tacos", Items: []SupplyRunItem{{Name: "tortillas"}}}}
+
+	if err := svc.PostSupplyRun(ctx, week, "Week 42 · Oct 12 – 18", groups); !errors.Is(err, ErrNotConfigured) {
+		t.Fatalf("PostSupplyRun without a webhook = %v, want ErrNotConfigured", err)
+	}
+	if _, err := svc.Put(ctx, testHook, "Family"); err != nil {
+		t.Fatal(err)
+	}
+	if err := svc.PostSupplyRun(ctx, week, "Week 42 · Oct 12 – 18", groups); err != nil {
+		t.Fatal(err)
+	}
+	reqs := f.requests()
+	if len(reqs) != 1 {
+		t.Fatalf("Chat got %d requests, want 1", len(reqs))
+	}
+	r := reqs[0]
+	if r.Query.Get("threadKey") != "mealquest-week-2026-W42" || r.Query.Get("messageReplyOption") != replyOption {
+		t.Errorf("threading = %v", r.Query)
+	}
+	if want := SupplyRunText("Week 42 · Oct 12 – 18", groups); r.Body["text"] != want {
+		t.Errorf("text = %q, want %q", r.Body["text"], want)
+	}
+	data, _ := json.Marshal(r.Body["cardsV2"])
+	var cards []cardV2
+	if err := json.Unmarshal(data, &cards); err != nil || len(cards) != 1 {
+		t.Fatalf("cardsV2 = %s, %v", data, err)
+	}
+	buttons := cards[0].Card.Sections[0].Widgets[0].ButtonList.Buttons
+	if cards[0].Card.Header.Title != "Supply run · Week 42 · Oct 12 – 18" || len(buttons) != 1 ||
+		buttons[0].OnClick.OpenLink.URL != "https://mealquest.example/plan/shopping?week=2026-10-12" {
+		t.Errorf("card = %s, want an Open button to the week's Supply run", data)
+	}
+
+	f.setStatus(http.StatusForbidden)
+	err := svc.PostSupplyRun(ctx, week, "Week 42 · Oct 12 – 18", groups)
+	if !errors.Is(err, ErrRefused) || !strings.Contains(err.Error(), "403") {
+		t.Errorf("PostSupplyRun answered 403 = %v, want ErrRefused with the status", err)
+	}
+	if err != nil {
+		assertNoSecret(t, "refused error", err.Error())
+	}
+
+	f.srv.Close()
+	err = svc.PostSupplyRun(ctx, week, "Week 42 · Oct 12 – 18", groups)
+	if !errors.Is(err, ErrUnreachable) {
+		t.Errorf("PostSupplyRun unanswered = %v, want ErrUnreachable", err)
+	}
+	if err != nil {
+		assertNoSecret(t, "unreachable error", err.Error())
+	}
+}

internal/chat/chattest/chattest.go

@@ -0,0 +1,97 @@
+// Package chattest provides a fake Google Chat incoming webhook for tests
+// of the features that post to Google Chat: an httptest server that
+// records each post and answers a status the test sets, reached through a
+// transport that sends chat.googleapis.com requests to it.
+package chattest
+
+import (
+	"encoding/json"
+	"io"
+	"net/http"
+	"net/http/httptest"
+	"net/url"
+	"sync"
+	"testing"
+)
+
+// Webhook is a valid Google Chat incoming webhook URL to store.
+const Webhook = "https://chat.googleapis.com/v1/spaces/AAQA1b2C3d4/messages?key=AIzaSyDdI0hCZtE6vySjMm-WEfRq3CPzqKqqsHI&token=q0Lz3kV9Yw8pXcRtN2bHsJdFgA7uEmKiOlP1nZxQ%3D"
+
+// Post is one message the fake received.
+type Post struct {
+	// Query is the request's query: key, token and any threading.
+	Query url.Values
+	// Body is the decoded JSON message.
+	Body map[string]any
+}
+
+// Text is the post's text.
+func (p Post) Text() string {
+	s, _ := p.Body["text"].(string)
+	return s
+}
+
+// Chat is a fake Google Chat endpoint. It answers 200 until SetStatus.
+type Chat struct {
+	srv    *httptest.Server
+	mu     sync.Mutex
+	status int
+	posts  []Post
+}
+
+// New starts a fake Google Chat endpoint, closed when the test ends.
+func New(t *testing.T) *Chat {
+	t.Helper()
+	c := &Chat{status: http.StatusOK}
+	c.srv = httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		data, _ := io.ReadAll(r.Body)
+		var body map[string]any
+		if err := json.Unmarshal(data, &body); err != nil {
+			t.Errorf("Google Chat post body %q: %v", data, err)
+		}
+		c.mu.Lock()
+		c.posts = append(c.posts, Post{Query: r.URL.Query(), Body: body})
+		status := c.status
+		c.mu.Unlock()
+		w.WriteHeader(status)
+	}))
+	t.Cleanup(c.srv.Close)
+	return c
+}
+
+// Transport sends every request to the fake, as if it were
+// chat.googleapis.com.
+func (c *Chat) Transport() http.RoundTripper {
+	return transport{c}
+}
+
+type transport struct{ c *Chat }
+
+func (tr transport) RoundTrip(req *http.Request) (*http.Response, error) {
+	target, err := url.Parse(tr.c.srv.URL)
+	if err != nil {
+		return nil, err
+	}
+	out := req.Clone(req.Context())
+	out.URL.Scheme, out.URL.Host = target.Scheme, target.Host
+	return http.DefaultTransport.RoundTrip(out)
+}
+
+// SetStatus makes the fake answer status from now on.
+func (c *Chat) SetStatus(status int) {
+	c.mu.Lock()
+	defer c.mu.Unlock()
+	c.status = status
+}
+
+// Close stops the fake, so posts get no answer.
+func (c *Chat) Close() {
+	c.srv.Close()
+}
+
+// Posts returns the messages received so far, in order.
+func (c *Chat) Posts() []Post {
+	c.mu.Lock()
+	defer c.mu.Unlock()
+	return append([]Post(nil), c.posts...)
+}

internal/chat/messages.go

@@ -3,6 +3,7 @@ package chat
 import (
 	"fmt"
 	"strings"
+	"time"
 
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/household"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/notify"
@@ -34,13 +35,16 @@ var actions = map[notify.EventType]string{
 // button.
 var carded = map[notify.EventType]bool{notify.PlanReady: true, notify.ListReady: true}
 
-// PlanReady is the plan_ready event of the week starting on week, naming
-// its dinners in plan order.
-func PlanReady(week store.LocalDate, dinners []string) notify.Event {
+// PlanReady is the plan_ready event of the week starting on week, drafted
+// in the week starting on thisWeek, naming its dinners in plan order. Its
+// title names the week as seen from thisWeek: "Next week's plan is ready",
+// "This week's plan is ready", or "The plan for the week of Oct 26 is
+// ready" for any other week.
+func PlanReady(week, thisWeek store.LocalDate, dinners []string) notify.Event {
 	return notify.Event{
 		Type:  notify.PlanReady,
 		Key:   string(notify.PlanReady) + ":" + week.String(),
-		Title: "This week's plan is ready",
+		Title: planTitle(week, thisWeek),
 		Body:  nameList(dinners),
 		URL:   "/plan",
 		Week:  week,
@@ -100,6 +104,72 @@ func RotationReview(dinnerID, name string, week store.LocalDate) notify.Event {
 	}
 }
 
+// SupplyRunItem is a Supply run item still needed, as sent to Google Chat;
+// Qty is empty when the recipe gives none.
+type SupplyRunItem struct {
+	Name string
+	Qty  string
+}
+
+// SupplyRunGroup is one dinner of a Supply run sent to Google Chat, with
+// its items still needed.
+type SupplyRunGroup struct {
+	Dinner string
+	Items  []SupplyRunItem
+}
+
+// SupplyRunText is the Google Chat message of the Supply run named name
+// (its title, or its week label until it has one): each dinner with items
+// still needed in bold, its items one per line, and the call to action.
+//
+//	Supply run · Week 42 · Oct 12 – 18
+//
+//	*Tacos*
+//	• ground beef — 1 lb
+//	• tortillas
+//
+//	Open the Supply run →
+//
+// A Supply run with nothing still needed says so.
+func SupplyRunText(name string, groups []SupplyRunGroup) string {
+	var b strings.Builder
+	b.WriteString("Supply run · " + name)
+	listed := false
+	for _, g := range groups {
+		if len(g.Items) == 0 {
+			continue
+		}
+		listed = true
+		b.WriteString("\n\n*" + g.Dinner + "*")
+		for _, it := range g.Items {
+			b.WriteString("\n• " + it.Name)
+			if it.Qty != "" {
+				b.WriteString(" — " + it.Qty)
+			}
+		}
+	}
+	if !listed {
+		b.WriteString("\n\nNothing left to buy.")
+	}
+	b.WriteString("\n\n" + actions[notify.ListReady] + " →")
+	return b.String()
+}
+
+// planTitle is the plan_ready title of the week starting on week, seen
+// from the week starting on thisWeek.
+func planTitle(week, thisWeek store.LocalDate) string {
+	y, m, d := thisWeek.Date()
+	next := store.LocalDateOf(time.Date(y, m, d+7, 0, 0, 0, 0, time.UTC))
+	switch week {
+	case thisWeek:
+		return "This week's plan is ready"
+	case next:
+		return "Next week's plan is ready"
+	}
+	_, m, d = week.Date()
+	return fmt.Sprintf("The plan for the week of %s %d is ready", m.String()[:3], d)
+}
+
 // Text is the Google Chat message of p: its title, its body after a colon
 // and the event's call to action with an arrow.
 func Text(p notify.Payload) string {

internal/chat/messages_test.go

@@ -36,7 +36,7 @@ func TestMessages(t *testing.T) {
 	}{
 		{
 			name:  "plan ready",
-			ev:    PlanReady(week, []string{"Tacos", "Bolognese", "Tikka masala", "Lemon orzo", "Bibimbap", "Shakshuka", "Chili"}),
+			ev:    PlanReady(week, week, []string{"Tacos", "Bolognese", "Tikka masala", "Lemon orzo", "Bibimbap", "Shakshuka", "Chili"}),
 			key:   "plan_ready:2026-10-12",
 			url:   "/plan",
 			week:  "2026-10-12",
@@ -46,7 +46,7 @@ func TestMessages(t *testing.T) {
 		},
 		{
 			name:  "plan ready with three dinners",
-			ev:    PlanReady(week, []string{"Tacos", "Bolognese", "Tikka masala"}),
+			ev:    PlanReady(week, week, []string{"Tacos", "Bolognese", "Tikka masala"}),
 			key:   "plan_ready:2026-10-12",
 			url:   "/plan",
 			week:  "2026-10-12",
@@ -54,6 +54,26 @@ func TestMessages(t *testing.T) {
 			body:  "Tacos, Bolognese, Tikka masala",
 			chatT: "This week's plan is ready: Tacos, Bolognese, Tikka masala. Open the plan →",
 		},
+		{
+			name:  "plan ready for next week",
+			ev:    PlanReady(week, mustDate(t, "2026-10-05"), []string{"Tacos", "Bolognese", "Tikka masala", "Lemon orzo"}),
+			key:   "plan_ready:2026-10-12",
+			url:   "/plan",
+			week:  "2026-10-12",
+			title: "Next week's plan is ready",
+			body:  "Tacos, Bolognese, Tikka masala + 1 more",
+			chatT: "Next week's plan is ready: Tacos, Bolognese, Tikka masala + 1 more. Open the plan →",
+		},
+		{
+			name:  "plan ready for a later week",
+			ev:    PlanReady(mustDate(t, "2026-10-26"), mustDate(t, "2026-10-05"), []string{"Tacos"}),
+			key:   "plan_ready:2026-10-26",
+			url:   "/plan",
+			week:  "2026-10-26",
+			title: "The plan for the week of Oct 26 is ready",
+			body:  "Tacos",
+			chatT: "The plan for the week of Oct 26 is ready: Tacos. Open the plan →",
+		},
 		{
 			name:  "list ready",
 			ev:    ListReady(week, 19, 7),
@@ -115,6 +135,23 @@ func TestMessages(t *testing.T) {
 	}
 }
 
+func TestSupplyRunText(t *testing.T) {
+	t.Parallel()
+	got := SupplyRunText("Week 42 · Oct 12 – 18", []SupplyRunGroup{
+		{Dinner: "Tacos", Items: []SupplyRunItem{{Name: "ground beef", Qty: "1 lb"}, {Name: "tortillas"}}},
+		{Dinner: "Bolognese"},
+		{Dinner: "Pho", Items: []SupplyRunItem{{Name: "rice noodles", Qty: "200 g"}}},
+	})
+	want := "Supply run · Week 42 · Oct 12 – 18\n\n*Tacos*\n• ground beef — 1 lb\n• tortillas\n\n*Pho*\n• rice noodles — 200 g\n\nOpen the Supply run →"
+	if got != want {
+		t.Errorf("SupplyRunText =\n%s\nwant\n%s", got, want)
+	}
+	got = SupplyRunText("Cozy week", []SupplyRunGroup{{Dinner: "Tacos"}})
+	if want := "Supply run · Cozy week\n\nNothing left to buy.\n\nOpen the Supply run →"; got != want {
+		t.Errorf("SupplyRunText with nothing needed = %q, want %q", got, want)
+	}
+}
+
 func TestTextWithoutBody(t *testing.T) {
 	t.Parallel()
 	got := Text(notify.Payload{Event: notify.PlanReady, Title: "This week's plan is ready", URL: "/plan"})

internal/db/models.go

@@ -276,15 +276,16 @@ type ShoppingItem struct {
 }
 
 type ShoppingList struct {
-	ID           string
-	WeekStart    string
-	PlanID       string
-	Title        sql.NullString
-	Status       string
-	SentToChatAt sql.NullString
-	FrozenAt     sql.NullString
-	CreatedAt    string
-	UpdatedAt    string
+	ID                    string
+	WeekStart             string
+	PlanID                string
+	Title                 sql.NullString
+	Status                string
+	SentToChatAt          sql.NullString
+	FrozenAt              sql.NullString
+	CreatedAt             string
+	UpdatedAt             string
+	ChatSendUnconfirmedAt sql.NullString
 }
 
 type Suggestion struct {

internal/db/querier.go

@@ -12,6 +12,10 @@ import (
 type Querier interface {
 	// An unknown id returns sql.ErrNoRows.
 	ArchiveDinner(ctx context.Context, arg ArchiveDinnerParams) (Dinner, error)
+	// Records a send of list id to Google Chat begun at
+	// chat_send_unconfirmed_at, before it is posted, unless the list is frozen
+	// into the Supply archive.
+	BeginShoppingListChatSend(ctx context.Context, arg BeginShoppingListChatSendParams) (int64, error)
 	// Leases the pending notification due longest ago by moving its
 	// next_attempt_at to lease_until, and returns it. A claimed row is not due
 	// again until the lease ends, so no other claim takes it while it is being
@@ -26,6 +30,8 @@ type Querier interface {
 	// sets last_sync_error, keeping the chosen calendar. Affects no row when
 	// nothing is connected.
 	ClearIntegrationsGoogleToken(ctx context.Context, arg ClearIntegrationsGoogleTokenParams) (int64, error)
+	// Clears the send of list id begun, once Google Chat refused it.
+	ClearShoppingListChatSend(ctx context.Context, arg ClearShoppingListChatSendParams) (int64, error)
 	// Drops references to the runs created before the cutoff, so the purge
 	// can delete them.
 	ClearSuggestionBatchAIRunsBefore(ctx context.Context, cutoff string) (int64, error)
@@ -143,6 +149,8 @@ type Querier interface {
 	GetShoppingList(ctx context.Context, weekStart string) (ShoppingList, error)
 	// A suggestion with its dinner. Returns sql.ErrNoRows for an unknown id.
 	GetSuggestion(ctx context.Context, id string) (GetSuggestionRow, error)
+	// Batch id. Returns sql.ErrNoRows when there is none.
+	GetSuggestionBatch(ctx context.Context, id string) (SuggestionBatch, error)
 	// The id of the job that runs batch batch_id.
 	GetSuggestionBatchJobID(ctx context.Context, arg GetSuggestionBatchJobIDParams) (string, error)
 	// The plan of the week starting week_start. Returns sql.ErrNoRows when
@@ -233,6 +241,9 @@ type Querier interface {
 	// Records a delivered notification; updated_at is when it was sent. The
 	// lease must still be the claim's.
 	MarkNotificationSent(ctx context.Context, arg MarkNotificationSentParams) (int64, error)
+	// Records list id sent to Google Chat at sent_to_chat_at, its send
+	// confirmed, unless it is frozen into the Supply archive.
+	MarkShoppingListSentToChat(ctx context.Context, arg MarkShoppingListSentToChatParams) (int64, error)
 	// Records an edit of plan id, raising its revision: a synced plan becomes
 	// changed, any other keeps its status.
 	MarkWeekPlanEdited(ctx context.Context, arg MarkWeekPlanEditedParams) error

internal/db/shopping.sql.go

@@ -10,6 +10,49 @@ import (
 	"database/sql"
 )
 
+const beginShoppingListChatSend = `-- name: BeginShoppingListChatSend :execrows
+UPDATE shopping_lists
+SET chat_send_unconfirmed_at = ?, updated_at = ?
+WHERE id = ? AND status = 'current' AND frozen_at IS NULL
+`
+
+type BeginShoppingListChatSendParams struct {
+	ChatSendUnconfirmedAt sql.NullString
+	UpdatedAt             string
+	ID                    string
+}
+
+// Records a send of list id to Google Chat begun at
+// chat_send_unconfirmed_at, before it is posted, unless the list is frozen
+// into the Supply archive.
+func (q *Queries) BeginShoppingListChatSend(ctx context.Context, arg BeginShoppingListChatSendParams) (int64, error) {
+	result, err := q.db.ExecContext(ctx, beginShoppingListChatSend, arg.ChatSendUnconfirmedAt, arg.UpdatedAt, arg.ID)
+	if err != nil {
+		return 0, err
+	}
+	return result.RowsAffected()
+}
+
+const clearShoppingListChatSend = `-- name: ClearShoppingListChatSend :execrows
+UPDATE shopping_lists
+SET chat_send_unconfirmed_at = NULL, updated_at = ?
+WHERE id = ?
+`
+
+type ClearShoppingListChatSendParams struct {
+	UpdatedAt string
+	ID        string
+}
+
+// Clears the send of list id begun, once Google Chat refused it.
+func (q *Queries) ClearShoppingListChatSend(ctx context.Context, arg ClearShoppingListChatSendParams) (int64, error) {
+	result, err := q.db.ExecContext(ctx, clearShoppingListChatSend, arg.UpdatedAt, arg.ID)
+	if err != nil {
+		return 0, err
+	}
+	return result.RowsAffected()
+}
+
 const createShoppingGroup = `-- name: CreateShoppingGroup :exec
 INSERT INTO shopping_groups (id, list_id, dinner_id, date, position, created_at, updated_at)
 VALUES (?, ?, ?, ?, ?, ?, ?)
@@ -135,7 +178,7 @@ func (q *Queries) FreezeShoppingList(ctx context.Context, arg FreezeShoppingList
 }
 
 const getShoppingItemList = `-- name: GetShoppingItemList :one
-SELECT shopping_lists.id, shopping_lists.week_start, shopping_lists.plan_id, shopping_lists.title, shopping_lists.status, shopping_lists.sent_to_chat_at, shopping_lists.frozen_at, shopping_lists.created_at, shopping_lists.updated_at
+SELECT shopping_lists.id, shopping_lists.week_start, shopping_lists.plan_id, shopping_lists.title, shopping_lists.status, shopping_lists.sent_to_chat_at, shopping_lists.frozen_at, shopping_lists.created_at, shopping_lists.updated_at, shopping_lists.chat_send_unconfirmed_at
 FROM shopping_items
 JOIN shopping_groups ON shopping_groups.id = shopping_items.group_id
 JOIN shopping_lists ON shopping_lists.id = shopping_groups.list_id
@@ -161,12 +204,13 @@ func (q *Queries) GetShoppingItemList(ctx context.Context, id string) (GetShoppi
 		&i.ShoppingList.FrozenAt,
 		&i.ShoppingList.CreatedAt,
 		&i.ShoppingList.UpdatedAt,
+		&i.ShoppingList.ChatSendUnconfirmedAt,
 	)
 	return i, err
 }
 
 const getShoppingList = `-- name: GetShoppingList :one
-SELECT id, week_start, plan_id, title, status, sent_to_chat_at, frozen_at, created_at, updated_at FROM shopping_lists
+SELECT id, week_start, plan_id, title, status, sent_to_chat_at, frozen_at, created_at, updated_at, chat_send_unconfirmed_at FROM shopping_lists
 WHERE week_start = ?
 `
 
@@ -185,6 +229,7 @@ func (q *Queries) GetShoppingList(ctx context.Context, weekStart string) (Shoppi
 		&i.FrozenAt,
 		&i.CreatedAt,
 		&i.UpdatedAt,
+		&i.ChatSendUnconfirmedAt,
 	)
 	return i, err
 }
@@ -322,7 +367,7 @@ func (q *Queries) ListShoppingItems(ctx context.Context, listID string) ([]ListS
 }
 
 const listShoppingListsThrough = `-- name: ListShoppingListsThrough :many
-SELECT id, week_start, plan_id, title, status, sent_to_chat_at, frozen_at, created_at, updated_at FROM shopping_lists
+SELECT id, week_start, plan_id, title, status, sent_to_chat_at, frozen_at, created_at, updated_at, chat_send_unconfirmed_at FROM shopping_lists
 WHERE week_start <= ?
 ORDER BY week_start DESC
 `
@@ -348,6 +393,7 @@ func (q *Queries) ListShoppingListsThrough(ctx context.Context, weekStart string
 			&i.FrozenAt,
 			&i.CreatedAt,
 			&i.UpdatedAt,
+			&i.ChatSendUnconfirmedAt,
 		); err != nil {
 			return nil, err
 		}
@@ -362,6 +408,28 @@ func (q *Queries) ListShoppingListsThrough(ctx context.Context, weekStart string
 	return items, nil
 }
 
+const markShoppingListSentToChat = `-- name: MarkShoppingListSentToChat :execrows
+UPDATE shopping_lists
+SET sent_to_chat_at = ?, chat_send_unconfirmed_at = NULL, updated_at = ?
+WHERE id = ? AND status = 'current' AND frozen_at IS NULL
+`
+
+type MarkShoppingListSentToChatParams struct {
+	SentToChatAt sql.NullString
+	UpdatedAt    string
+	ID           string
+}
+
+// Records list id sent to Google Chat at sent_to_chat_at, its send
+// confirmed, unless it is frozen into the Supply archive.
+func (q *Queries) MarkShoppingListSentToChat(ctx context.Context, arg MarkShoppingListSentToChatParams) (int64, error) {
+	result, err := q.db.ExecContext(ctx, markShoppingListSentToChat, arg.SentToChatAt, arg.UpdatedAt, arg.ID)
+	if err != nil {
+		return 0, err
+	}
+	return result.RowsAffected()
+}
+
 const moveShoppingGroup = `-- name: MoveShoppingGroup :exec
 UPDATE shopping_groups
 SET position = ?, updated_at = ?

internal/db/suggestions.sql.go

@@ -259,6 +259,26 @@ func (q *Queries) GetSuggestion(ctx context.Context, id string) (GetSuggestionRo
 	return i, err
 }
 
+const getSuggestionBatch = `-- name: GetSuggestionBatch :one
+SELECT id, "trigger", status, ai_run_id, created_at, updated_at FROM suggestion_batches
+WHERE id = ?
+`
+
+// Batch id. Returns sql.ErrNoRows when there is none.
+func (q *Queries) GetSuggestionBatch(ctx context.Context, id string) (SuggestionBatch, error) {
+	row := q.db.QueryRowContext(ctx, getSuggestionBatch, id)
+	var i SuggestionBatch
+	err := row.Scan(
+		&i.ID,
+		&i.Trigger,
+		&i.Status,
+		&i.AiRunID,
+		&i.CreatedAt,
+		&i.UpdatedAt,
+	)
+	return i, err
+}
+
 const getSuggestionBatchJobID = `-- name: GetSuggestionBatchJobID :one
 SELECT id FROM jobs
 WHERE kind = ?1

internal/notify/notify.go

@@ -6,7 +6,8 @@
 // row in notification_outbox keyed by (event key, channel). The event key is
 // the caller's idempotency key, so emitting the same event twice stores
 // nothing the second time and never touches a row already stored, whatever
-// its status.
+// its status. EmitTx does the same inside the caller's transaction, so an
+// event is stored with the change it is about; the caller then calls Wake.
 //
 // The worker started by Start delivers due rows through the Sender
 // registered for their channel. A delivered row is marked sent. A failed
@@ -142,6 +143,20 @@ func NewService(st *store.Store, logger *slog.Logger) (*Service, error) {
 // row with ev.Key is left as it is. An invalid event is ErrInvalidEvent and
 // stores nothing; a type with no preference row is an error.
 func (s *Service) Emit(ctx context.Context, ev Event) error {
+	err := s.st.WithTx(ctx, func(tx *sql.Tx) error {
+		return s.EmitTx(ctx, tx, ev)
+	})
+	if err != nil {
+		return err
+	}
+	s.Wake()
+	return nil
+}
+
+// EmitTx stores ev's notifications as Emit does, in tx, so they are
+// committed with the change the event is about or not at all. The caller
+// calls Wake once tx has committed.
+func (s *Service) EmitTx(ctx context.Context, tx *sql.Tx, ev Event) error {
 	if err := validate(ev); err != nil {
 		return err
 	}
@@ -154,42 +169,33 @@ func (s *Service) Emit(ctx context.Context, ev Event) error {
 		return fmt.Errorf("notify: encode payload of %s: %w", ev.Key, err)
 	}
 
-	var queued []Channel
-	err = s.st.WithTx(ctx, func(tx *sql.Tx) error {
-		q := db.New(tx)
-		pref, err := q.GetNotificationPref(ctx, string(ev.Type))
-		if errors.Is(err, sql.ErrNoRows) {
-			return fmt.Errorf("notify: no notification preference for %s", ev.Type)
-		}
-		if err != nil {
-			return fmt.Errorf("notify: read notification preference for %s: %w", ev.Type, err)
-		}
-		now := timestamp(s.now())
-		for _, ch := range enabledChannels(pref) {
-			n, err := q.InsertNotification(ctx, db.InsertNotificationParams{
-				ID:            store.NewID(),
-				EventKey:      ev.Key,
-				Channel:       string(ch),
-				Payload:       string(data),
-				NextAttemptAt: sql.NullString{String: now, Valid: true},
-				Now:           now,
-			})
-			if err != nil {
-				return fmt.Errorf("notify: store %s notification %s: %w", ch, ev.Key, err)
-			}
-			if n == 1 {
-				queued = append(queued, ch)
-			}
-		}
-		return nil
-	})
+	q := db.New(tx)
+	pref, err := q.GetNotificationPref(ctx, string(ev.Type))
+	if errors.Is(err, sql.ErrNoRows) {
+		return fmt.Errorf("notify: no notification preference for %s", ev.Type)
+	}
 	if err != nil {
-		return err
+		return fmt.Errorf("notify: read notification preference for %s: %w", ev.Type, err)
 	}
-	s.logger.InfoContext(ctx, "notification emitted", "event_key", ev.Key, "queued", queued)
-	if len(queued) > 0 {
-		s.wakeWorker()
+	now := timestamp(s.now())
+	var queued []Channel
+	for _, ch := range enabledChannels(pref) {
+		n, err := q.InsertNotification(ctx, db.InsertNotificationParams{
+			ID:            store.NewID(),
+			EventKey:      ev.Key,
+			Channel:       string(ch),
+			Payload:       string(data),
+			NextAttemptAt: sql.NullString{String: now, Valid: true},
+			Now:           now,
+		})
+		if err != nil {
+			return fmt.Errorf("notify: store %s notification %s: %w", ch, ev.Key, err)
+		}
+		if n == 1 {
+			queued = append(queued, ch)
+		}
 	}
+	s.logger.InfoContext(ctx, "notification stored in transaction", "event_key", ev.Key, "queued", queued)
 	return nil
 }
 

internal/notify/notify_test.go

@@ -753,3 +753,34 @@ func TestWorkerDeliversEmittedEvent(t *testing.T) {
 		t.Fatalf("%d deliveries, want 1", n)
 	}
 }
+
+// TestEmitTxCommitsWithTheCallersTransaction: EmitTx's rows are stored only
+// when the caller's transaction commits.
+func TestEmitTxCommitsWithTheCallersTransaction(t *testing.T) {
+	ctx := context.Background()
+	svc, st, _ := newTestService(t)
+	setPref(t, st, PlanReady, true, false)
+	const key = "plan_ready:2026-10-12"
+	rollback := errors.New("roll back")
+	err := st.WithTx(ctx, func(tx *sql.Tx) error {
+		if err := svc.EmitTx(ctx, tx, planReady(key)); err != nil {
+			return err
+		}
+		return rollback
+	})
+	if !errors.Is(err, rollback) {
+		t.Fatalf("WithTx = %v", err)
+	}
+	if rows := outbox(t, st, key); len(rows) != 0 {
+		t.Fatalf("rows after rollback = %v, want none", rows)
+	}
+	if err := st.WithTx(ctx, func(tx *sql.Tx) error { return svc.EmitTx(ctx, tx, planReady(key)) }); err != nil {
+		t.Fatal(err)
+	}
+	if r := onlyRow(t, st, key, ChannelPush); r.Status != "pending" {
+		t.Errorf("row after commit = %+v, want pending", r)
+	}
+	if err := st.WithTx(ctx, func(tx *sql.Tx) error { return svc.EmitTx(ctx, tx, Event{Type: PlanReady, Key: key}) }); !errors.Is(err, ErrInvalidEvent) {
+		t.Errorf("EmitTx of an invalid event = %v, want ErrInvalidEvent", err)
+	}
+}

internal/notify/notifytest/notifytest.go

@@ -0,0 +1,65 @@
+// Package notifytest builds notify services for tests of the features that
+// emit notifications, and reads back what they stored.
+package notifytest
+
+import (
+	"encoding/json"
+	"io"
+	"log/slog"
+	"testing"
+
+	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/household"
+	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/notify"
+	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/store"
+)
+
+// New returns a notify service over st, with st's notification preferences
+// seeded, so every event type goes to push and plan_ready and list_ready to
+// Google Chat too. Its worker is not started: what is emitted stays pending.
+func New(t *testing.T, st *store.Store) *notify.Service {
+	t.Helper()
+	if err := household.SeedNotificationPrefs(t.Context(), st); err != nil {
+		t.Fatal(err)
+	}
+	svc, err := notify.NewService(st, slog.New(slog.NewTextHandler(io.Discard, nil)))
+	if err != nil {
+		t.Fatal(err)
+	}
+	return svc
+}
+
+// Row is one stored notification.
+type Row struct {
+	Key     string
+	Channel notify.Channel
+	Payload notify.Payload
+}
+
+// Rows returns every notification stored in st whose event is of type ev,
+// oldest first.
+func Rows(t *testing.T, st *store.Store, ev notify.EventType) []Row {
+	t.Helper()
+	rs, err := st.Reader.QueryContext(t.Context(),
+		`SELECT event_key, channel, payload FROM notification_outbox WHERE event_key LIKE ? ORDER BY created_at, channel`,
+		string(ev)+":%")
+	if err != nil {
+		t.Fatal(err)
+	}
+	defer rs.Close()
+	var out []Row
+	for rs.Next() {
+		var r Row
+		var payload string
+		if err := rs.Scan(&r.Key, &r.Channel, &payload); err != nil {
+			t.Fatal(err)
+		}
+		if err := json.Unmarshal([]byte(payload), &r.Payload); err != nil {
+			t.Fatal(err)
+		}
+		out = append(out, r)
+	}
+	if err := rs.Err(); err != nil {
+		t.Fatal(err)
+	}
+	return out
+}

internal/notify/worker.go

@@ -104,8 +104,9 @@ func (s *Service) Wait() {
 	s.wg.Wait()
 }
 
-// wakeWorker gives the worker a token to look for due rows.
-func (s *Service) wakeWorker() {
+// Wake tells the worker to look for due rows, as after EmitTx's
+// transaction commits.
+func (s *Service) Wake() {
 	select {
 	case s.wake <- struct{}{}:
 	default: // the worker already has a token and will look again

internal/plan/draft.go

@@ -10,6 +10,7 @@ import (
 
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/ai/harness"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/ai/skills"
+	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/chat"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/db"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/dinners"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/household"
@@ -147,6 +148,12 @@ func (s *Service) request(ctx context.Context, weekStart store.LocalDate) (skill
 // draft_week was given: a day whose dinner is no longer in it, or is in it
 // as a Regular rather than the Quest log or the other way round, leaves
 // everything as it is, failing with ReasonPoolChanged.
+//
+// A stored draft emits plan_ready, keyed by the week, in the same
+// transaction, naming the drafted dinners Monday to Sunday. The key is the week's,
+// so only the AI's first draft of a week notifies: a redraft (Rebuild week)
+// stores no second notification. A manual swap never drafts, so never
+// notifies.
 func (s *Service) storeDraft(ctx context.Context, weekStart, thisWeek store.LocalDate, confirm bool, base int64, week skills.Week) (string, error) {
 	var planID string
 	err := s.st.WithTx(ctx, func(tx *sql.Tx) error {
@@ -156,8 +163,10 @@ func (s *Service) storeDraft(ctx context.Context, weekStart, thisWeek store.Loca
 			return fmt.Errorf("plan: list draft pool: %w", err)
 		}
 		pool := make(map[string]string, len(rows))
+		names := make(map[string]string, len(rows))
 		for _, d := range rows {
 			pool[d.ID] = d.Status
+			names[d.ID] = d.Name
 		}
 		for _, d := range week.Days {
 			status, ok := pool[d.DinnerID]
@@ -215,11 +224,16 @@ func (s *Service) storeDraft(ctx context.Context, weekStart, thisWeek store.Loca
 				return fmt.Errorf("plan: put %s of %s: %w", d.Date, planID, err)
 			}
 		}
-		return nil
+		planned := make([]string, len(week.Days))
+		for i, d := range week.Days {
+			planned[i] = names[d.DinnerID]
+		}
+		return s.notifier.EmitTx(ctx, tx, chat.PlanReady(weekStart, thisWeek, planned))
 	})
 	if err != nil {
 		return "", err
 	}
+	s.notifier.Wake()
 	return planID, nil
 }
 

internal/plan/plan.go

@@ -22,10 +22,12 @@ import (
 	"time"
 
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/ai/skills"
+	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/chat"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/db"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/dinners"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/household"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/jobs"
+	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/notify"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/store"
 )
 
@@ -138,6 +140,7 @@ type Service struct {
 	st       *store.Store
 	draft    Drafter
 	cal      Calendar
+	notifier *notify.Service
 	logger   *slog.Logger
 	draftJob *jobs.Kind[DraftJob]
 	// publicURL is MEALQUEST_PUBLIC_URL, under which a pushed event links
@@ -146,11 +149,12 @@ type Service struct {
 }
 
 // NewService returns a service over st that drafts with draft, pushes to
-// cal with links under publicURL, and registers the KindDraftWeek job on
+// cal with links under publicURL, tells the household through notifier,
+// which must be over st, and registers the KindDraftWeek job on
 // runner, which must not have started yet. The kind is service-only:
 // StartDraft, which keeps one draft in flight per week, is the only way to
 // enqueue it.
-func NewService(st *store.Store, draft Drafter, runner *jobs.Runner, cal Calendar, publicURL *url.URL, logger *slog.Logger) (*Service, error) {
+func NewService(st *store.Store, draft Drafter, runner *jobs.Runner, cal Calendar, notifier *notify.Service, publicURL *url.URL, logger *slog.Logger) (*Service, error) {
 	switch {
 	case st == nil:
 		return nil, errors.New("plan: nil store")
@@ -160,12 +164,14 @@ func NewService(st *store.Store, draft Drafter, runner *jobs.Runner, cal Calenda
 		return nil, errors.New("plan: nil job runner")
 	case cal == nil:
 		return nil, errors.New("plan: nil calendar")
+	case notifier == nil:
+		return nil, errors.New("plan: nil notifier")
 	case publicURL == nil:
 		return nil, errors.New("plan: nil public URL")
 	case logger == nil:
 		return nil, errors.New("plan: nil logger")
 	}
-	s := &Service{st: st, draft: draft, cal: cal, logger: logger, publicURL: publicURL}
+	s := &Service{st: st, draft: draft, cal: cal, notifier: notifier, logger: logger, publicURL: publicURL}
 	kind, err := jobs.Register(runner, KindDraftWeek, s.runDraft, Reasons...)
 	if err != nil {
 		return nil, err
@@ -226,6 +232,30 @@ func (s *Service) Get(ctx context.Context, weekStart store.LocalDate) (p Plan, e
 	return readPlan(ctx, db.New(tx), weekStart)
 }
 
+// EmitDayOfReminder emits day_of_reminder for date, keyed by the date,
+// naming the dinner planned on it, and reports whether it did: a date whose
+// week has no plan emits nothing. The scheduler calls it at the
+// household's reminder_time (Feature 20); emitting a date again stores no
+// second notification.
+func (s *Service) EmitDayOfReminder(ctx context.Context, date store.LocalDate) (bool, error) {
+	p, err := s.Get(ctx, household.WeekStart(date))
+	if errors.Is(err, ErrNotFound) {
+		return false, nil
+	}
+	if err != nil {
+		return false, err
+	}
+	for _, d := range p.Days {
+		if d.Date == date.String() {
+			if err := s.notifier.Emit(ctx, chat.DayOfReminder(date, d.Dinner.ID, d.Dinner.Name)); err != nil {
+				return false, fmt.Errorf("plan: %w", err)
+			}
+			return true, nil
+		}
+	}
+	return false, fmt.Errorf("plan: week %s has no day %s", p.WeekStart, date)
+}
+
 // readPlan reads the plan of the week starting weekStart through q, with
 // each day's start_by from the household's dinner time and zone.
 func readPlan(ctx context.Context, q *db.Queries, weekStart store.LocalDate) (Plan, error) {

internal/plan/plan_test.go

@@ -20,11 +20,14 @@ import (
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/ai/harness"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/ai/llm"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/ai/skills"
+	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/chat"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/db"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/gcal"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/gcal/gcaltest"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/household"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/jobs"
+	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/notify"
+	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/notify/notifytest"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/plan"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/secretbox"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/store"
@@ -143,7 +146,7 @@ func newEnv(t *testing.T) *env {
 	if err != nil {
 		t.Fatal(err)
 	}
-	e.svc, err = plan.NewService(st, drafter, e.runner, e.gcal, publicURL, logger)
+	e.svc, err = plan.NewService(st, drafter, e.runner, e.gcal, notifytest.New(t, st), publicURL, logger)
 	if err != nil {
 		t.Fatal(err)
 	}
@@ -352,6 +355,85 @@ func TestDraftCreatesPlan(t *testing.T) {
 	}
 }
 
+// TestDraftEmitsPlanReady: the AI's first draft of a week stores plan_ready
+// keyed by the week, on push and Google Chat, naming the dinners Monday to
+// Sunday; a redraft (Rebuild week) and a manual swap store nothing more.
+func TestDraftEmitsPlanReady(t *testing.T) {
+	e := newEnv(t)
+	e.start(t)
+	e.reply("", fullWeek...)
+	e.mustDraft(t, false)
+
+	zone, err := time.LoadLocation("America/New_York")
+	if err != nil {
+		t.Fatal(err)
+	}
+	want := chat.PlanReady(week, household.WeekStart(household.Today(time.Now(), zone)), fullWeek)
+	rows := notifytest.Rows(t, e.st, notify.PlanReady)
+	if len(rows) != 2 || rows[0].Channel != notify.ChannelChat || rows[1].Channel != notify.ChannelPush {
+		t.Fatalf("plan_ready rows = %+v, want one on chat and one on push", rows)
+	}
+	for _, r := range rows {
+		p := r.Payload
+		if r.Key != "plan_ready:2026-10-12" || p.Tag != r.Key || p.URL != "/plan" || p.Week != "2026-10-12" ||
+			p.Title != want.Title || p.Body != "Beef Chili, Pot Roast, Pad Thai + 4 more" {
+			t.Errorf("%s row = %+v, want key plan_ready:2026-10-12, title %q, the drafted dinners and /plan", r.Channel, r, want.Title)
+		}
+	}
+
+	reversed := slices.Clone(fullWeek)
+	slices.Reverse(reversed)
+	e.reply("", reversed...)
+	e.mustDraft(t, false)
+	e.ids["Fish Tacos"] = e.dinner(t, "Fish Tacos", "regular", "stovetop", 25)
+	if _, err := e.svc.Swap(t.Context(), week, "2026-10-14", e.ids["Fish Tacos"]); err != nil {
+		t.Fatal(err)
+	}
+	if again := notifytest.Rows(t, e.st, notify.PlanReady); !slices.Equal(again, rows) {
+		t.Errorf("plan_ready rows after a redraft and a swap = %+v, want the first draft's only", again)
+	}
+}
+
+// TestFailedDraftEmitsNothing: a draft that stores no plan notifies no one.
+func TestFailedDraftEmitsNothing(t *testing.T) {
+	e := newEnv(t)
+	e.start(t)
+	e.model.QueueGenerate(llm.GenerateResult{Err: errors.New("provider down")})
+	if job := e.draft(t, false); job.Status != jobs.StatusFailed {
+		t.Fatalf("job %s, want failed", job.Status)
+	}
+	if rows := notifytest.Rows(t, e.st, notify.PlanReady); len(rows) != 0 {
+		t.Errorf("plan_ready rows = %+v, want none", rows)
+	}
+}
+
+// TestEmitDayOfReminder: the reminder of a planned date names its dinner,
+// keyed by the date; a date with no plan emits nothing, and a date emitted
+// again stores nothing more.
+func TestEmitDayOfReminder(t *testing.T) {
+	e := newEnv(t)
+	e.start(t)
+	if ok, err := e.svc.EmitDayOfReminder(t.Context(), mustDate("2026-10-14")); ok || err != nil {
+		t.Fatalf("EmitDayOfReminder with no plan = %v, %v, want false", ok, err)
+	}
+	e.reply("", fullWeek...)
+	e.mustDraft(t, false)
+	for range 2 {
+		if ok, err := e.svc.EmitDayOfReminder(t.Context(), mustDate("2026-10-14")); !ok || err != nil {
+			t.Fatalf("EmitDayOfReminder = %v, %v, want true", ok, err)
+		}
+	}
+	rows := notifytest.Rows(t, e.st, notify.DayOfReminder)
+	if len(rows) != 1 {
+		t.Fatalf("day_of_reminder rows = %+v, want one on push", rows)
+	}
+	r := rows[0]
+	if r.Key != "day_of_reminder:2026-10-14" || r.Channel != notify.ChannelPush || r.Payload.Title != "Tonight's dinner" ||
+		r.Payload.Body != "Pad Thai" || r.Payload.URL != "/dinner/"+e.ids["Pad Thai"] || r.Payload.Week != "2026-10-12" {
+		t.Errorf("day_of_reminder row = %+v", r)
+	}
+}
+
 func TestStartByIsDinnerTimeMinusMinutesForCrockPot(t *testing.T) {
 	e := newEnv(t)
 	e.start(t)

internal/server/plans_test.go

@@ -17,11 +17,14 @@ import (
 
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/ai/harness"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/ai/skills"
+	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/chat"
+	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/chat/chattest"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/db"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/gcal"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/gcal/gcaltest"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/household"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/jobs"
+	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/notify/notifytest"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/plan"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/shopping"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/store"
@@ -44,6 +47,10 @@ type plansEnv struct {
 	// unconnected.
 	google *gcaltest.Google
 	gcal   *gcal.Service
+	// chat is the fake Google Chat endpoint chatSvc posts to; no webhook
+	// is stored until a test stores one.
+	chat    *chattest.Chat
+	chatSvc *chat.Service
 	// logs holds every log line the router writes.
 	logs *bytes.Buffer
 }
@@ -85,15 +92,21 @@ func newPlansRouterTitled(t *testing.T, title shopping.Titler) plansEnv {
 	if err != nil {
 		t.Fatal(err)
 	}
-	svc, err := plan.NewService(st, fail, runner, googleSvc, pub, logger)
+	notifier := notifytest.New(t, st)
+	svc, err := plan.NewService(st, fail, runner, googleSvc, notifier, pub, logger)
 	if err != nil {
 		t.Fatal(err)
 	}
-	shop, err := shopping.NewService(st, title, runner, logger)
+	fakeChat := chattest.New(t)
+	chatSvc, err := chat.NewService(st, newTestBox(t), pub, fakeChat.Transport())
 	if err != nil {
 		t.Fatal(err)
 	}
-	h, err := NewRouter(logger, "dev", nil, stubAuth{}, stubSessions{}, newTestSettings(t), newTestSearch(t), newTestAI(t), newTestChat(t),
+	shop, err := shopping.NewService(st, title, runner, notifier, chatSvc, logger)
+	if err != nil {
+		t.Fatal(err)
+	}
+	h, err := NewRouter(logger, "dev", nil, stubAuth{}, stubSessions{}, newTestSettings(t), newTestSearch(t), newTestAI(t), chatSvc,
 		newTestDinners(t), newTestSuggest(t), svc, shop, googleSvc, newTestPush(t), runner, newTestPhotos(t), fstest.MapFS{"index.html": {Data: []byte(fixtureIndex)}})
 	if err != nil {
 		t.Fatal(err)
@@ -129,7 +142,7 @@ func newPlansRouterTitled(t *testing.T, title shopping.Titler) plansEnv {
 		}
 	}
 	return plansEnv{h: h, st: st, svc: svc, shop: shop, runner: runner, questLog: dinner("Pad Thai", "quest_log", "stovetop", 35),
-		google: google, gcal: googleSvc, logs: logs}
+		google: google, gcal: googleSvc, chat: fakeChat, chatSvc: chatSvc, logs: logs}
 }
 
 func (e plansEnv) setStatus(t *testing.T, status string) {

internal/server/server.go

@@ -163,6 +163,7 @@ func NewRouter(logger *slog.Logger, version string, trusted forwarded.Trusted, a
 	apiV1.Get("/shopping/archive", getSupplyArchive(logger, shopSvc))
 	apiV1.Get("/shopping/{weekStart}", getSupplyRun(logger, shopSvc))
 	apiV1.Post("/shopping/{weekStart}/generate", postSupplyRunGenerate(logger, shopSvc))
+	apiV1.Post("/shopping/{weekStart}/send-chat", postSupplyRunSendChat(logger, shopSvc))
 	apiV1.Patch("/shopping/items/{id}", patchShoppingItem(logger, shopSvc))
 	apiV1.Get("/rotation-reviews", getRotationReviews(logger, planSvc))
 	apiV1.Post("/dinners/{id}/rotation-review", postRotationReview(logger, planSvc))

internal/server/server_test.go

@@ -26,6 +26,7 @@ import (
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/gcal"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/household"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/jobs"
+	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/notify/notifytest"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/plan"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/recipes"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/recipes/recipestest"
@@ -186,7 +187,7 @@ func newTestSuggest(t *testing.T) *suggest.Service {
 	fail := func(context.Context, string, skills.SideQuestsRequest) (skills.SideQuests, error) {
 		return skills.SideQuests{}, errors.New("no model in this test")
 	}
-	svc, err := suggest.NewService(st, g, fail, runner, logger)
+	svc, err := suggest.NewService(st, g, fail, runner, notifytest.New(t, st), logger)
 	if err != nil {
 		t.Fatal(err)
 	}
@@ -206,7 +207,7 @@ func newTestPlan(t *testing.T) *plan.Service {
 	fail := func(context.Context, string, skills.WeekRequest) (skills.Week, error) {
 		return skills.Week{}, errors.New("no model in this test")
 	}
-	svc, err := plan.NewService(st, fail, runner, newTestGoogle(t), &url.URL{Scheme: "https", Host: "mealquest.example"}, logger)
+	svc, err := plan.NewService(st, fail, runner, newTestGoogle(t), notifytest.New(t, st), &url.URL{Scheme: "https", Host: "mealquest.example"}, logger)
 	if err != nil {
 		t.Fatal(err)
 	}
@@ -214,7 +215,8 @@ func newTestPlan(t *testing.T) *plan.Service {
 }
 
 // newTestShopping returns a shopping service over a migrated temp
-// database, whose Supply runs stay untitled.
+// database, whose Supply runs stay untitled and whose posts to Google Chat
+// all fail.
 func newTestShopping(t *testing.T) *shopping.Service {
 	t.Helper()
 	st := newTestStore(t)
@@ -223,7 +225,7 @@ func newTestShopping(t *testing.T) *shopping.Service {
 	if err != nil {
 		t.Fatal(err)
 	}
-	svc, err := shopping.NewService(st, untitled, runner, logger)
+	svc, err := shopping.NewService(st, untitled, runner, notifytest.New(t, st), newTestChat(t), logger)
 	if err != nil {
 		t.Fatal(err)
 	}

internal/server/shopping.go

@@ -9,6 +9,7 @@ import (
 
 	"github.com/go-chi/chi/v5"
 
+	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/chat"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/household"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/shopping"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/store"
@@ -17,6 +18,9 @@ import (
 // maxShoppingItemBody bounds a PATCH /shopping/items/{id} body.
 const maxShoppingItemBody = 1 << 10
 
+// maxSendChatBody bounds a POST /shopping/{weekStart}/send-chat body.
+const maxSendChatBody = 1 << 10
+
 // supplyRun is a Supply run as the API shows it. label is the week label,
 // which stands in for title until the AI writes one.
 type supplyRun struct {
@@ -25,6 +29,9 @@ type supplyRun struct {
 	Title        *string `json:"title"`
 	Status       string  `json:"status"`
 	SentToChatAt *string `json:"sent_to_chat_at"`
+	// ChatSendUnconfirmedAt is when a send to Google Chat whose outcome is
+	// not known began.
+	ChatSendUnconfirmedAt *string `json:"chat_send_unconfirmed_at"`
 	shopping.Counts
 	Groups []supplyRunGroup `json:"groups"`
 }
@@ -59,6 +66,12 @@ type generatedSupplyRun struct {
 	Skipped []shopping.SkippedDay `json:"skipped"`
 }
 
+// sendChatRequest is the POST /shopping/{weekStart}/send-chat body:
+// resend posts a week already sent again.
+type sendChatRequest struct {
+	Resend bool `json:"resend"`
+}
+
 // shoppingItemPatch is the PATCH /shopping/items/{id} body.
 type shoppingItemPatch struct {
 	Needed *bool `json:"needed"`
@@ -120,6 +133,53 @@ func postSupplyRunGenerate(logger *slog.Logger, svc *shopping.Service) http.Hand
 	}
 }
 
+// postSupplyRunSendChat posts the week's Supply run to Google Chat and
+// answers with it, sent_to_chat_at recorded. Its body is a JSON object,
+// {} or {"resend": true}: a week already sent, or with a send
+// unconfirmed, is answered as it is, without a second post, unless resend
+// is true. No webhook stored is 409 not_configured; a send whose outcome is
+// not known (Google Chat did not answer, or its acceptance could not be
+// recorded) 502 chat_unconfirmed, not retryable, since retrying could post
+// twice; and Google Chat refusing the message 502 chat_refused, retryable
+// only for 429 or 5xx.
+func postSupplyRunSendChat(logger *slog.Logger, svc *shopping.Service) http.HandlerFunc {
+	return func(w http.ResponseWriter, r *http.Request) {
+		week, ok := weekStartOrFail(w, r, logger)
+		if !ok {
+			return
+		}
+		body, err := decodePatch[sendChatRequest](http.MaxBytesReader(w, r.Body, maxSendChatBody))
+		if err != nil {
+			writeError(w, r, logger, http.StatusBadRequest, "invalid_request", err.Error())
+			return
+		}
+		l, err := svc.SendToChat(r.Context(), week, body.Resend)
+		var refused *chat.RefusedError
+		switch {
+		case errors.Is(err, chat.ErrNotConfigured):
+			writeError(w, r, logger, http.StatusConflict, "not_configured", "no Google Chat webhook is configured; add one in Settings")
+			return
+		case errors.Is(err, shopping.ErrSendUnconfirmed):
+			logger.WarnContext(r.Context(), "send Supply run to Google Chat", "error", err)
+			writeAPIError(w, r, logger, http.StatusBadGateway, apiError{Code: "chat_unconfirmed", Message: shopping.ErrSendUnconfirmed.Error()})
+			return
+		case errors.As(err, &refused):
+			logger.WarnContext(r.Context(), "send Supply run to Google Chat", "error", err)
+			writeAPIError(w, r, logger, http.StatusBadGateway, apiError{Code: "chat_refused", Message: err.Error(), Retryable: refused.Retryable()})
+			return
+		case err != nil:
+			writeShoppingError(w, r, logger, "send Supply run to Google Chat", err)
+			return
+		}
+		out, err := supplyRunOf(week, l)
+		if err != nil {
+			writeShoppingError(w, r, logger, "send Supply run to Google Chat", err)
+			return
+		}
+		writeJSON(w, r, logger, http.StatusOK, out)
+	}
+}
+
 // patchShoppingItem marks a Supply run item needed or "have it" and
 // answers with its Supply run's new counts.
 func patchShoppingItem(logger *slog.Logger, svc *shopping.Service) http.HandlerFunc {
@@ -232,13 +292,14 @@ func supplyRunOf(week store.LocalDate, l shopping.List) (supplyRun, error) {
 		}
 	}
 	return supplyRun{
-		WeekStart:    l.WeekStart,
-		Label:        label,
-		Title:        l.Title,
-		Status:       l.Status,
-		SentToChatAt: l.SentToChatAt,
-		Counts:       l.Counts(),
-		Groups:       groups,
+		WeekStart:             l.WeekStart,
+		Label:                 label,
+		Title:                 l.Title,
+		Status:                l.Status,
+		SentToChatAt:          l.SentToChatAt,
+		ChatSendUnconfirmedAt: l.ChatSendUnconfirmedAt,
+		Counts:                l.Counts(),
+		Groups:                groups,
 	}, nil
 }
 

internal/server/shopping_test.go

@@ -15,6 +15,7 @@ import (
 
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/ai/harness"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/ai/skills"
+	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/chat/chattest"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/db"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/household"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/plan"
@@ -82,14 +83,15 @@ func (e plansEnv) archive(t *testing.T) {
 // supplyRunJSON is a Supply run answer decoded with every field the API
 // promises.
 type supplyRunJSON struct {
-	WeekStart    string  `json:"weekStart"`
-	Label        string  `json:"label"`
-	Title        *string `json:"title"`
-	Status       string  `json:"status"`
-	SentToChatAt *string `json:"sent_to_chat_at"`
-	NeededCount  int     `json:"needed_count"`
-	TotalCount   int     `json:"total_count"`
-	Groups       []struct {
+	WeekStart             string  `json:"weekStart"`
+	Label                 string  `json:"label"`
+	Title                 *string `json:"title"`
+	Status                string  `json:"status"`
+	SentToChatAt          *string `json:"sent_to_chat_at"`
+	ChatSendUnconfirmedAt *string `json:"chat_send_unconfirmed_at"`
+	NeededCount           int     `json:"needed_count"`
+	TotalCount            int     `json:"total_count"`
+	Groups                []struct {
 		Dinner struct {
 			ID   string `json:"id"`
 			Name string `json:"name"`
@@ -184,7 +186,7 @@ func TestSupplyRunShape(t *testing.T) {
 	if status != http.StatusOK {
 		t.Fatalf("generate = %d %v", status, raw)
 	}
-	wantTop := []string{"groups", "label", "needed_count", "sent_to_chat_at", "skipped", "status", "title", "total_count", "weekStart"}
+	wantTop := []string{"chat_send_unconfirmed_at", "groups", "label", "needed_count", "sent_to_chat_at", "skipped", "status", "title", "total_count", "weekStart"}
 	if got := keys(raw); !reflect.DeepEqual(got, wantTop) {
 		t.Errorf("generate fields = %v, want %v", got, wantTop)
 	}
@@ -787,3 +789,124 @@ func TestSupplyArchive(t *testing.T) {
 		t.Errorf("frozen list = %s %d/%d %v, want archived 2/3 %v", frozen.Status, frozen.NeededCount, frozen.TotalCount, frozen.render(), wantLines)
 	}
 }
+
+// TestSupplyRunSendChat posts the week's Supply run to Google Chat once,
+// records sent_to_chat_at, answers a second send with the status as it
+// is, and posts again only with resend.
+func TestSupplyRunSendChat(t *testing.T) {
+	t.Parallel()
+	e := newPlansRouter(t)
+	e.groundWeek(t)
+	var l supplyRunJSON
+	callShopping(t, e, http.MethodPost, shoppingPath+"2026-10-12/generate", "", &l)
+	callShopping(t, e, http.MethodPatch, shoppingPath+"items/"+l.itemID(t, "onion"), `{"needed":false}`, nil)
+	send := shoppingPath + "2026-10-12/send-chat"
+
+	if status, body := callShopping(t, e, http.MethodPost, send, `{}`, nil); status != http.StatusConflict || errorCode(body) != "not_configured" {
+		t.Fatalf("send with no webhook = %d %v, want 409 not_configured", status, body)
+	}
+	if _, err := e.chatSvc.Put(t.Context(), chattest.Webhook, "Family"); err != nil {
+		t.Fatal(err)
+	}
+
+	var sent supplyRunJSON
+	if status, body := callShopping(t, e, http.MethodPost, send, `{}`, &sent); status != http.StatusOK {
+		t.Fatalf("send = %d %v", status, body)
+	}
+	if sent.SentToChatAt == nil || sent.WeekStart != "2026-10-12" || !reflect.DeepEqual(sent.render(), []string{
+		"Monday 2026-10-12 Beef Chili: ground beef [1 lb] needed",
+		"Monday 2026-10-12 Beef Chili: kidney beans [2 cans] needed",
+		"Monday 2026-10-12 Beef Chili: onion [1] have it",
+		"Tuesday 2026-10-13 Regular 2026-10-13: spaghetti [500 g] needed",
+		"Tuesday 2026-10-13 Regular 2026-10-13: basil [null] needed",
+	}) {
+		t.Errorf("send answer = %+v, want the Supply run with sent_to_chat_at", sent)
+	}
+	posts := e.chat.Posts()
+	if len(posts) != 1 {
+		t.Fatalf("Google Chat got %d posts, want 1", len(posts))
+	}
+	want := "Supply run · Week 42 · Oct 12 – 18\n\n*Beef Chili*\n• ground beef — 1 lb\n• kidney beans — 2 cans\n\n" +
+		"*Regular 2026-10-13*\n• spaghetti — 500 g\n• basil\n\nOpen the Supply run →"
+	if posts[0].Text() != want {
+		t.Errorf("posted text = %q, want %q", posts[0].Text(), want)
+	}
+
+	var again supplyRunJSON
+	if status, body := callShopping(t, e, http.MethodPost, send, `{}`, &again); status != http.StatusOK || again.SentToChatAt == nil || *again.SentToChatAt != *sent.SentToChatAt {
+		t.Errorf("send again = %d %v, sent_to_chat_at %v, want 200 and %s", status, body, again.SentToChatAt, *sent.SentToChatAt)
+	}
+	if n := len(e.chat.Posts()); n != 1 {
+		t.Errorf("send again without resend posted: %d posts, want 1", n)
+	}
+	var got supplyRunJSON
+	callShopping(t, e, http.MethodGet, shoppingPath+"2026-10-12", "", &got)
+	if got.SentToChatAt == nil || *got.SentToChatAt != *sent.SentToChatAt {
+		t.Errorf("GET sent_to_chat_at = %v, want %s", got.SentToChatAt, *sent.SentToChatAt)
+	}
+
+	var resent supplyRunJSON
+	if status, body := callShopping(t, e, http.MethodPost, send, `{"resend":true}`, &resent); status != http.StatusOK || resent.SentToChatAt == nil {
+		t.Fatalf("resend = %d %v", status, body)
+	}
+	if n := len(e.chat.Posts()); n != 2 {
+		t.Errorf("resend: %d posts, want 2", n)
+	}
+}
+
+func TestSupplyRunSendChatErrors(t *testing.T) {
+	t.Parallel()
+	e := newPlansRouter(t)
+	e.groundWeek(t)
+	callShopping(t, e, http.MethodPost, shoppingPath+"2026-10-12/generate", "", nil)
+	if _, err := e.chatSvc.Put(t.Context(), chattest.Webhook, "Family"); err != nil {
+		t.Fatal(err)
+	}
+	for _, tc := range []struct {
+		name, path, body string
+		status           int
+		code             string
+	}{
+		{"no body", "2026-10-12/send-chat", "", http.StatusBadRequest, "invalid_request"},
+		{"resend not a boolean", "2026-10-12/send-chat", `{"resend":"yes"}`, http.StatusBadRequest, "invalid_request"},
+		{"unknown field", "2026-10-12/send-chat", `{"force":true}`, http.StatusBadRequest, "invalid_request"},
+		{"not a Monday", "2026-10-13/send-chat", `{}`, http.StatusBadRequest, "invalid_week"},
+		{"no list", "2026-10-19/send-chat", `{}`, http.StatusNotFound, "not_found"},
+	} {
+		status, body := callShopping(t, e, http.MethodPost, shoppingPath+tc.path, tc.body, nil)
+		if status != tc.status || errorCode(body) != tc.code {
+			t.Errorf("%s = %d %v, want %d %s", tc.name, status, body, tc.status, tc.code)
+		}
+	}
+
+	e.chat.SetStatus(http.StatusInternalServerError)
+	status, body := callShopping(t, e, http.MethodPost, shoppingPath+"2026-10-12/send-chat", `{}`, nil)
+	if status != http.StatusBadGateway || errorCode(body) != "chat_refused" || body["error"].(map[string]any)["retryable"] != true {
+		t.Errorf("send Google Chat refuses = %d %v, want 502 chat_refused, retryable", status, body)
+	}
+	e.chat.SetStatus(http.StatusNotFound)
+	status, body = callShopping(t, e, http.MethodPost, shoppingPath+"2026-10-12/send-chat", `{}`, nil)
+	if status != http.StatusBadGateway || errorCode(body) != "chat_refused" || body["error"].(map[string]any)["retryable"] != false {
+		t.Errorf("send Google Chat answers 404 = %d %v, want 502 chat_refused, not retryable", status, body)
+	}
+	var l supplyRunJSON
+	callShopping(t, e, http.MethodGet, shoppingPath+"2026-10-12", "", &l)
+	if l.SentToChatAt != nil || l.ChatSendUnconfirmedAt != nil {
+		t.Errorf("after refused sends sent_to_chat_at = %v, chat_send_unconfirmed_at = %v, want both null", l.SentToChatAt, l.ChatSendUnconfirmedAt)
+	}
+	e.chat.Close()
+	status, body = callShopping(t, e, http.MethodPost, shoppingPath+"2026-10-12/send-chat", `{}`, nil)
+	if status != http.StatusBadGateway || errorCode(body) != "chat_unconfirmed" || body["error"].(map[string]any)["retryable"] != false {
+		t.Errorf("send Google Chat does not answer = %d %v, want 502 chat_unconfirmed, not retryable", status, body)
+	}
+	callShopping(t, e, http.MethodGet, shoppingPath+"2026-10-12", "", &l)
+	if l.SentToChatAt != nil || l.ChatSendUnconfirmedAt == nil {
+		t.Errorf("after an unanswered send sent_to_chat_at = %v, chat_send_unconfirmed_at = %v, want null and set", l.SentToChatAt, l.ChatSendUnconfirmedAt)
+	}
+
+	e.archive(t)
+	status, body = callShopping(t, e, http.MethodPost, shoppingPath+"2026-10-12/send-chat", `{"resend":true}`, nil)
+	if status != http.StatusConflict || errorCode(body) != "archived" {
+		t.Errorf("send an archived list = %d %v, want 409 archived", status, body)
+	}
+}

internal/server/suggestions_test.go

@@ -17,6 +17,7 @@ import (
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/ai/skills"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/db"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/jobs"
+	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/notify/notifytest"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/recipes/recipestest"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/store"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/suggest"
@@ -40,7 +41,7 @@ func newSuggestionsRouter(t *testing.T, names ...string) (http.Handler, *store.S
 	fail := func(context.Context, string, skills.SideQuestsRequest) (skills.SideQuests, error) {
 		return skills.SideQuests{}, errors.New("no model in this test")
 	}
-	svc, err := suggest.NewService(st, g, fail, runner, logger)
+	svc, err := suggest.NewService(st, g, fail, runner, notifytest.New(t, st), logger)
 	if err != nil {
 		t.Fatal(err)
 	}

internal/shopping/chat.go

@@ -0,0 +1,106 @@
+package shopping
+
+import (
+	"context"
+	"database/sql"
+	"errors"
+	"fmt"
+
+	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/chat"
+	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/db"
+	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/household"
+	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/jobs"
+	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/store"
+)
+
+// SendToChat posts the Supply run of the week starting weekStart to Google
+// Chat (chat.PostSupplyRun): each dinner with its items still needed, and a
+// link to the Supply run. It records sent_to_chat_at and returns the list.
+//
+// A week is sent once: a Supply run already sent, or with a send
+// unconfirmed, is returned as it is, without posting again, unless resend
+// is true. A week with no Supply run is ErrListNotFound and one frozen into
+// the Supply archive ErrFrozen.
+//
+// The send is recorded as begun, in chat_send_unconfirmed_at, before it is
+// posted, so a post whose outcome is lost is never taken for one never
+// made. A post Google Chat refuses, or that is never made, returns
+// chat.PostSupplyRun's error and clears it. A post Google Chat does not
+// answer, or one it accepts that cannot then be recorded, is
+// ErrSendUnconfirmed and leaves it, as does the process stopping mid-send.
+func (s *Service) SendToChat(ctx context.Context, weekStart store.LocalDate, resend bool) (List, error) {
+	s.sending.Lock()
+	defer s.sending.Unlock()
+	l, err := s.Get(ctx, weekStart)
+	if err != nil {
+		return List{}, err
+	}
+	if l.Status != StatusCurrent {
+		return List{}, ErrFrozen
+	}
+	if (l.SentToChatAt != nil || l.ChatSendUnconfirmedAt != nil) && !resend {
+		return l, nil
+	}
+	name, err := household.WeekLabel(weekStart)
+	if err != nil {
+		return List{}, fmt.Errorf("shopping: send to Google Chat: %w", err)
+	}
+	if l.Title != nil {
+		name = *l.Title
+	}
+	groups := make([]chat.SupplyRunGroup, len(l.Groups))
+	for i, g := range l.Groups {
+		groups[i].Dinner = g.DinnerName
+		for _, it := range g.Items {
+			if !it.Needed {
+				continue
+			}
+			item := chat.SupplyRunItem{Name: it.Name}
+			if it.Qty != nil {
+				item.Qty = *it.Qty
+			}
+			groups[i].Items = append(groups[i].Items, item)
+		}
+	}
+	q := db.New(s.st.Writer)
+	n, err := q.BeginShoppingListChatSend(ctx, db.BeginShoppingListChatSendParams{
+		ChatSendUnconfirmedAt: sql.NullString{String: store.Now().String(), Valid: true},
+		UpdatedAt:             store.Now().String(),
+		ID:                    l.ID,
+	})
+	if err != nil {
+		return List{}, fmt.Errorf("shopping: record send to Google Chat begun: %w", err)
+	}
+	if n != 1 {
+		return List{}, ErrFrozen
+	}
+	postErr := s.chat.PostSupplyRun(ctx, weekStart, name, groups)
+	// The post's outcome is known: record it even if the client has gone.
+	write, cancel := jobs.FinalWriteContext(ctx)
+	defer cancel()
+	if errors.Is(postErr, chat.ErrUnreachable) {
+		return List{}, fmt.Errorf("%w: %w", ErrSendUnconfirmed, postErr)
+	}
+	if postErr != nil {
+		if _, err := q.ClearShoppingListChatSend(write, db.ClearShoppingListChatSendParams{
+			UpdatedAt: store.Now().String(),
+			ID:        l.ID,
+		}); err != nil {
+			return List{}, errors.Join(postErr, fmt.Errorf("shopping: clear refused send to Google Chat: %w", err))
+		}
+		return List{}, postErr
+	}
+	now := store.Now().String()
+	n, err = q.MarkShoppingListSentToChat(write, db.MarkShoppingListSentToChatParams{
+		SentToChatAt: sql.NullString{String: now, Valid: true},
+		UpdatedAt:    now,
+		ID:           l.ID,
+	})
+	if err != nil {
+		return List{}, fmt.Errorf("%w: record sent to Google Chat: %w", ErrSendUnconfirmed, err)
+	}
+	if n != 1 {
+		return List{}, ErrFrozen
+	}
+	return s.Get(write, weekStart)
+}

internal/shopping/notify_test.go

@@ -0,0 +1,242 @@
+package shopping_test
+
+import (
+	"errors"
+	"net/http"
+	"slices"
+	"testing"
+
+	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/chat"
+	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/chat/chattest"
+	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/notify"
+	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/notify/notifytest"
+	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/shopping"
+)
+
+// TestGenerateEmitsListReadyOnce: the week's first Supply run stores
+// list_ready keyed by the week, on push and Google Chat; remaking it, and
+// making it again after Push to Calendar, stores nothing more.
+func TestGenerateEmitsListReadyOnce(t *testing.T) {
+	e := newEnv(t)
+	e.dinner(t, "Beef Chili", ing{"ground beef", "1", "lb"}, ing{"onion", "1", ""})
+	e.dinner(t, "Pad Thai", ing{"rice noodles", "8", "oz"})
+	e.dinner(t, "Pot Roast")
+	e.plan(t, "Beef Chili", "Pad Thai", "Pot Roast")
+
+	if _, err := e.svc.Generate(t.Context(), mustDate("2026-10-19")); !errors.Is(err, shopping.ErrPlanNotFound) {
+		t.Fatalf("Generate of a week with no plan = %v", err)
+	}
+	if rows := notifytest.Rows(t, e.st, notify.ListReady); len(rows) != 0 {
+		t.Fatalf("list_ready rows after a failed generation = %+v, want none", rows)
+	}
+
+	e.generate(t)
+	rows := notifytest.Rows(t, e.st, notify.ListReady)
+	if len(rows) != 2 || rows[0].Channel != notify.ChannelChat || rows[1].Channel != notify.ChannelPush {
+		t.Fatalf("list_ready rows = %+v, want one on chat and one on push", rows)
+	}
+	for _, r := range rows {
+		p := r.Payload
+		if r.Key != "list_ready:2026-10-12" || p.URL != "/plan/shopping" || p.Week != "2026-10-12" ||
+			p.Title != "This week's Supply run is ready" || p.Body != "3 items to buy for 2 dinners" {
+			t.Errorf("%s row = %+v, want list_ready:2026-10-12, 3 items for 2 dinners, /plan/shopping", r.Channel, r)
+		}
+	}
+
+	e.swap(t, "2026-10-14", "Pad Thai")
+	e.swap(t, "2026-10-13", "Pot Roast")
+	e.generate(t)
+	if _, err := e.svc.GeneratePushed(t.Context(), week, planRevision(t, e)); err != nil {
+		t.Fatal(err)
+	}
+	if again := notifytest.Rows(t, e.st, notify.ListReady); !slices.Equal(again, rows) {
+		t.Errorf("list_ready rows after remaking = %+v, want the first list's only", again)
+	}
+}
+
+// planRevision is the revision of the env's plan.
+func planRevision(t *testing.T, e *env) int64 {
+	t.Helper()
+	var rev int64
+	if err := e.st.Reader.QueryRow(`SELECT revision FROM week_plans WHERE id = ?`, e.planID).Scan(&rev); err != nil {
+		t.Fatal(err)
+	}
+	return rev
+}
+
+// TestSendToChat posts the Supply run's needed items by dinner, records
+// sent_to_chat_at, sends a week once, and again only with resend.
+func TestSendToChat(t *testing.T) {
+	e := newEnv(t)
+	e.dinner(t, "Beef Chili", ing{"ground beef", "1", "lb"}, ing{"onion", "1", ""})
+	e.dinner(t, "Pad Thai", ing{"rice noodles", "8", "oz"})
+	e.plan(t, "Beef Chili", "Pad Thai")
+	l := e.generate(t).List
+	e.haveIt(t, l, "Pad Thai", "rice noodles")
+	if _, err := e.chatSvc.Put(t.Context(), chattest.Webhook, "Family"); err != nil {
+		t.Fatal(err)
+	}
+
+	sent, err := e.svc.SendToChat(t.Context(), week, false)
+	if err != nil {
+		t.Fatal(err)
+	}
+	if sent.SentToChatAt == nil {
+		t.Fatal("sent_to_chat_at not recorded")
+	}
+	posts := e.chat.Posts()
+	if len(posts) != 1 {
+		t.Fatalf("Google Chat got %d posts, want 1", len(posts))
+	}
+	want := chat.SupplyRunText("Week 42 · Oct 12 – 18", []chat.SupplyRunGroup{
+		{Dinner: "Beef Chili", Items: []chat.SupplyRunItem{{Name: "ground beef", Qty: "1 lb"}, {Name: "onion", Qty: "1"}}},
+		{Dinner: "Pad Thai"},
+	})
+	if posts[0].Text() != want {
+		t.Errorf("posted text = %q, want %q", posts[0].Text(), want)
+	}
+	if posts[0].Query.Get("threadKey") != chat.ThreadKey(week) {
+		t.Errorf("posted in thread %q, want %q", posts[0].Query.Get("threadKey"), chat.ThreadKey(week))
+	}
+	if got, err := e.svc.Get(t.Context(), week); err != nil || got.SentToChatAt == nil || *got.SentToChatAt != *sent.SentToChatAt {
+		t.Errorf("stored sent_to_chat_at = %v, %v, want %s", got.SentToChatAt, err, *sent.SentToChatAt)
+	}
+
+	again, err := e.svc.SendToChat(t.Context(), week, false)
+	if err != nil {
+		t.Fatal(err)
+	}
+	if n := len(e.chat.Posts()); n != 1 || *again.SentToChatAt != *sent.SentToChatAt {
+		t.Errorf("send again without resend: %d posts, sent_to_chat_at %s, want 1 post and %s", n, *again.SentToChatAt, *sent.SentToChatAt)
+	}
+
+	if _, err := e.st.Writer.Exec(`UPDATE shopping_lists SET title = 'Chili and noodles'`); err != nil {
+		t.Fatal(err)
+	}
+	resent, err := e.svc.SendToChat(t.Context(), week, true)
+	if err != nil {
+		t.Fatal(err)
+	}
+	posts = e.chat.Posts()
+	if len(posts) != 2 || *resent.SentToChatAt < *sent.SentToChatAt {
+		t.Fatalf("resend: %d posts, sent_to_chat_at %s, want 2 posts and a later time than %s", len(posts), *resent.SentToChatAt, *sent.SentToChatAt)
+	}
+	if want := "Supply run · Chili and noodles"; posts[1].Text()[:len(want)] != want {
+		t.Errorf("resent text = %q, want it headed by the title", posts[1].Text())
+	}
+}
+
+// TestSendToChatFailuresRecordNothing: a send with no webhook, or one
+// Google Chat refuses, leaves sent_to_chat_at and chat_send_unconfirmed_at
+// unset; a week with no list, or a frozen one, is refused without posting.
+func TestSendToChatFailuresRecordNothing(t *testing.T) {
+	e := newEnv(t)
+	e.dinner(t, "Beef Chili", ing{"ground beef", "1", "lb"})
+	e.plan(t, "Beef Chili")
+
+	if _, err := e.svc.SendToChat(t.Context(), week, false); !errors.Is(err, shopping.ErrListNotFound) {
+		t.Errorf("SendToChat with no list = %v, want ErrListNotFound", err)
+	}
+	e.generate(t)
+	if _, err := e.svc.SendToChat(t.Context(), week, false); !errors.Is(err, chat.ErrNotConfigured) {
+		t.Errorf("SendToChat with no webhook = %v, want chat.ErrNotConfigured", err)
+	}
+	if _, err := e.chatSvc.Put(t.Context(), chattest.Webhook, "Family"); err != nil {
+		t.Fatal(err)
+	}
+	e.chat.SetStatus(http.StatusInternalServerError)
+	if _, err := e.svc.SendToChat(t.Context(), week, false); !errors.Is(err, chat.ErrRefused) {
+		t.Errorf("SendToChat answered 500 = %v, want chat.ErrRefused", err)
+	}
+	if l, err := e.svc.Get(t.Context(), week); err != nil || l.SentToChatAt != nil || l.ChatSendUnconfirmedAt != nil {
+		t.Errorf("after failed sends sent_to_chat_at = %v, chat_send_unconfirmed_at = %v, %v, want both unset", l.SentToChatAt, l.ChatSendUnconfirmedAt, err)
+	}
+
+	if _, err := e.st.Writer.Exec(`UPDATE shopping_lists SET status = 'archived', frozen_at = '2026-10-19T04:05:00Z'`); err != nil {
+		t.Fatal(err)
+	}
+	posts := len(e.chat.Posts())
+	if _, err := e.svc.SendToChat(t.Context(), week, true); !errors.Is(err, shopping.ErrFrozen) {
+		t.Errorf("SendToChat of a frozen list = %v, want ErrFrozen", err)
+	}
+	if n := len(e.chat.Posts()); n != posts {
+		t.Errorf("a frozen list was posted")
+	}
+}
+
+// TestSendToChatUnconfirmed: a send whose outcome is not known, because
+// Google Chat accepted the post but recording it failed, or did not answer,
+// is ErrSendUnconfirmed and leaves the send unconfirmed rather than unsent:
+// a send without resend does not post again, and one with resend does,
+// confirming it.
+func TestSendToChatUnconfirmed(t *testing.T) {
+	e := newEnv(t)
+	e.dinner(t, "Beef Chili", ing{"ground beef", "1", "lb"})
+	e.plan(t, "Beef Chili")
+	e.generate(t)
+	if _, err := e.chatSvc.Put(t.Context(), chattest.Webhook, "Family"); err != nil {
+		t.Fatal(err)
+	}
+	if _, err := e.st.Writer.Exec(`CREATE TRIGGER refuse_sent BEFORE UPDATE OF sent_to_chat_at ON shopping_lists BEGIN SELECT RAISE(ABORT, 'sent refused'); END`); err != nil {
+		t.Fatal(err)
+	}
+
+	if _, err := e.svc.SendToChat(t.Context(), week, false); !errors.Is(err, shopping.ErrSendUnconfirmed) {
+		t.Fatalf("SendToChat accepted but not recorded = %v, want ErrSendUnconfirmed", err)
+	}
+	if n := len(e.chat.Posts()); n != 1 {
+		t.Fatalf("Google Chat got %d posts, want 1", n)
+	}
+	l, err := e.svc.Get(t.Context(), week)
+	if err != nil || l.SentToChatAt != nil || l.ChatSendUnconfirmedAt == nil {
+		t.Fatalf("after an unrecorded send sent_to_chat_at = %v, chat_send_unconfirmed_at = %v, %v, want unset and set", l.SentToChatAt, l.ChatSendUnconfirmedAt, err)
+	}
+	if _, err := e.st.Writer.Exec(`DROP TRIGGER refuse_sent`); err != nil {
+		t.Fatal(err)
+	}
+
+	again, err := e.svc.SendToChat(t.Context(), week, false)
+	if err != nil {
+		t.Fatal(err)
+	}
+	if n := len(e.chat.Posts()); n != 1 || again.ChatSendUnconfirmedAt == nil || *again.ChatSendUnconfirmedAt != *l.ChatSendUnconfirmedAt {
+		t.Errorf("send again without resend: %d posts, chat_send_unconfirmed_at %v, want 1 post and %s", n, again.ChatSendUnconfirmedAt, *l.ChatSendUnconfirmedAt)
+	}
+
+	resent, err := e.svc.SendToChat(t.Context(), week, true)
+	if err != nil {
+		t.Fatal(err)
+	}
+	if n := len(e.chat.Posts()); n != 2 || resent.SentToChatAt == nil || resent.ChatSendUnconfirmedAt != nil {
+		t.Errorf("resend: %d posts, sent_to_chat_at %v, chat_send_unconfirmed_at %v, want 2 posts, set and unset", n, resent.SentToChatAt, resent.ChatSendUnconfirmedAt)
+	}
+
+	e.chat.Close()
+	if _, err := e.svc.SendToChat(t.Context(), week, true); !errors.Is(err, shopping.ErrSendUnconfirmed) || !errors.Is(err, chat.ErrUnreachable) {
+		t.Errorf("SendToChat unanswered = %v, want ErrSendUnconfirmed and chat.ErrUnreachable", err)
+	}
+	if l, err := e.svc.Get(t.Context(), week); err != nil || l.SentToChatAt == nil || *l.SentToChatAt != *resent.SentToChatAt || l.ChatSendUnconfirmedAt == nil {
+		t.Errorf("after an unanswered resend sent_to_chat_at = %v, chat_send_unconfirmed_at = %v, %v, want %s and set", l.SentToChatAt, l.ChatSendUnconfirmedAt, err, *resent.SentToChatAt)
+	}
+}
+
+// TestSendToChatPostsOnlyOnceBegun: a send that cannot be recorded as
+// begun is not posted.
+func TestSendToChatPostsOnlyOnceBegun(t *testing.T) {
+	e := newEnv(t)
+	e.dinner(t, "Beef Chili", ing{"ground beef", "1", "lb"})
+	e.plan(t, "Beef Chili")
+	e.generate(t)
+	if _, err := e.chatSvc.Put(t.Context(), chattest.Webhook, "Family"); err != nil {
+		t.Fatal(err)
+	}
+	if _, err := e.st.Writer.Exec(`CREATE TRIGGER refuse_begin BEFORE UPDATE OF chat_send_unconfirmed_at ON shopping_lists WHEN NEW.chat_send_unconfirmed_at IS NOT NULL BEGIN SELECT RAISE(ABORT, 'begin refused'); END`); err != nil {
+		t.Fatal(err)
+	}
+	if _, err := e.svc.SendToChat(t.Context(), week, false); err == nil {
+		t.Fatal("SendToChat not recorded as begun succeeded, want an error")
+	}
+	if n := len(e.chat.Posts()); n != 0 {
+		t.Errorf("Google Chat got %d posts of a send not recorded as begun, want 0", n)
+	}
+}

internal/shopping/shopping.go

@@ -27,10 +27,12 @@ import (
 	"time"
 
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/ai/skills"
+	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/chat"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/db"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/dinners"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/household"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/jobs"
+	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/notify"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/store"
 )
 
@@ -80,6 +82,12 @@ var ErrItemNotFound = errors.New("no Supply run has that item")
 // the household's time zone.
 var ErrWeekNotEnded = errors.New("the week has not ended")
 
+// ErrSendUnconfirmed is a send to Google Chat whose outcome is not known:
+// Google Chat did not answer, or accepted the post but recording it failed.
+// The post may have been made, so the Supply run keeps the send as
+// unconfirmed and is posted again only with resend.
+var ErrSendUnconfirmed = errors.New("the shopping list may have reached Google Chat, but that could not be confirmed; check the space before sending again")
+
 // ErrInvalidPeriod is an Archive grouping other than ByWeek, ByMonth and
 // ByYear.
 var ErrInvalidPeriod = errors.New("by must be week, month or year")
@@ -95,6 +103,8 @@ type Service struct {
 	st       *store.Store
 	title    Titler
 	titleJob *jobs.Kind[TitleJob]
+	notifier *notify.Service
+	chat     *chat.Service
 	logger   *slog.Logger
 	// now is the clock weeks are ended and current on; tests replace it.
 	now func() time.Time
@@ -104,12 +114,17 @@ type Service struct {
 	// waits for the title jobs in flight to store their titles or fail,
 	// and no title job runs archive_title while a freeze is under way.
 	titling sync.RWMutex
+	// sending serializes SendToChat, so a week is posted to Google Chat
+	// once however many sends race.
+	sending sync.Mutex
 }
 
 // NewService returns a service over st that titles Supply runs with title
-// in KindTitleSupplyRun jobs, which it registers on runner, and logs to
-// logger. runner must not have started yet.
-func NewService(st *store.Store, title Titler, runner *jobs.Runner, logger *slog.Logger) (*Service, error) {
+// in KindTitleSupplyRun jobs, which it registers on runner, tells the
+// household through notifier, which must be over st, sends Supply runs to
+// Google Chat through chatSvc, and logs to logger. runner must not have
+// started yet.
+func NewService(st *store.Store, title Titler, runner *jobs.Runner, notifier *notify.Service, chatSvc *chat.Service, logger *slog.Logger) (*Service, error) {
 	switch {
 	case st == nil:
 		return nil, errors.New("shopping: nil store")
@@ -117,10 +132,14 @@ func NewService(st *store.Store, title Titler, runner *jobs.Runner, logger *slog
 		return nil, errors.New("shopping: nil titler")
 	case runner == nil:
 		return nil, errors.New("shopping: nil job runner")
+	case notifier == nil:
+		return nil, errors.New("shopping: nil notifier")
+	case chatSvc == nil:
+		return nil, errors.New("shopping: nil chat service")
 	case logger == nil:
 		return nil, errors.New("shopping: nil logger")
 	}
-	s := &Service{st: st, title: title, logger: logger, now: time.Now}
+	s := &Service{st: st, title: title, notifier: notifier, chat: chatSvc, logger: logger, now: time.Now}
 	kind, err := jobs.Register(runner, KindTitleSupplyRun, s.runTitleJob, ReasonTitleFailed)
 	if err != nil {
 		return nil, err
@@ -145,7 +164,11 @@ type List struct {
 	// SentToChatAt is when the list was sent to Google Chat; nil until it
 	// is.
 	SentToChatAt *string `json:"sent_to_chat_at"`
-	Groups       []Group `json:"groups"`
+	// ChatSendUnconfirmedAt is when a send to Google Chat whose outcome is
+	// not known began: one under way, or one that may or may not have been
+	// posted. nil when there is none.
+	ChatSendUnconfirmedAt *string `json:"chat_send_unconfirmed_at"`
+	Groups                []Group `json:"groups"`
 }
 
 // Counts are how many items of a Supply run are still needed and how many
@@ -272,6 +295,7 @@ func (s *Service) generate(ctx context.Context, weekStart store.LocalDate, check
 		return Generated{}, fmt.Errorf("shopping: generate: %w", err)
 	}
 	var out Generated
+	notified := false
 	err := s.st.WithTx(ctx, func(tx *sql.Tx) error {
 		q := db.New(tx)
 		plan, err := q.GetWeekPlan(ctx, weekStart.String())
@@ -293,8 +317,9 @@ func (s *Service) generate(ctx context.Context, weekStart store.LocalDate, check
 		if err != nil && !errors.Is(err, sql.ErrNoRows) {
 			return fmt.Errorf("shopping: read list: %w", err)
 		}
+		created := err != nil
 		switch {
-		case err != nil: // no list yet
+		case created: // no list yet
 			list = db.ShoppingList{ID: store.NewID(), WeekStart: weekStart.String(), PlanID: plan.ID, Status: StatusCurrent}
 			err = q.CreateShoppingList(ctx, db.CreateShoppingListParams{
 				ID: list.ID, WeekStart: list.WeekStart, PlanID: list.PlanID, CreatedAt: now, UpdatedAt: now,
@@ -313,6 +338,13 @@ func (s *Service) generate(ctx context.Context, weekStart store.LocalDate, check
 			return err
 		}
 		out = Generated{List: listOf(list, groups), Skipped: skipped}
+		if created {
+			ev := chat.ListReady(weekStart, out.List.Counts().Needed, len(groups))
+			if err := s.notifier.EmitTx(ctx, tx, ev); err != nil {
+				return fmt.Errorf("shopping: %w", err)
+			}
+			notified = true
+		}
 		if list.Title.Valid {
 			return nil
 		}
@@ -331,6 +363,9 @@ func (s *Service) generate(ctx context.Context, weekStart store.LocalDate, check
 	if out.TitleJobID != nil {
 		s.titleJob.Wake()
 	}
+	if notified {
+		s.notifier.Wake()
+	}
 	return out, nil
 }
 
@@ -538,13 +573,14 @@ func frozen(list db.ShoppingList) bool {
 // listOf is list with groups.
 func listOf(list db.ShoppingList, groups []Group) List {
 	return List{
-		ID:           list.ID,
-		WeekStart:    list.WeekStart,
-		PlanID:       list.PlanID,
-		Title:        nullString(list.Title),
-		Status:       list.Status,
-		SentToChatAt: nullString(list.SentToChatAt),
-		Groups:       groups,
+		ID:                    list.ID,
+		WeekStart:             list.WeekStart,
+		PlanID:                list.PlanID,
+		Title:                 nullString(list.Title),
+		Status:                list.Status,
+		SentToChatAt:          nullString(list.SentToChatAt),
+		ChatSendUnconfirmedAt: nullString(list.ChatSendUnconfirmedAt),
+		Groups:                groups,
 	}
 }
 

internal/shopping/shopping_test.go

@@ -3,11 +3,14 @@ package shopping_test
 import (
 	"bytes"
 	"context"
+	"crypto/rand"
 	"database/sql"
+	"encoding/base64"
 	"errors"
 	"fmt"
 	"io"
 	"log/slog"
+	"net/url"
 	"reflect"
 	"strings"
 	"sync"
@@ -17,10 +20,14 @@ import (
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/ai/harness"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/ai/llm"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/ai/skills"
+	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/chat"
+	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/chat/chattest"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/db"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/dinners"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/jobs"
+	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/notify/notifytest"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/recipes/recipestest"
+	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/secretbox"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/shopping"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/store"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/migrations"
@@ -61,6 +68,10 @@ type env struct {
 	beforeModel func(llm.Request)
 	// log holds what the service logged.
 	log *syncBuffer
+	// chat is the fake Google Chat endpoint chatSvc posts to; no webhook
+	// is stored until a test stores one.
+	chat    *chattest.Chat
+	chatSvc *chat.Service
 }
 
 // syncBuffer is a bytes.Buffer safe for concurrent use.
@@ -122,7 +133,18 @@ func newEnv(t *testing.T) *env {
 	if err != nil {
 		t.Fatal(err)
 	}
-	e.svc, err = shopping.NewService(st, title, e.runner, logger)
+	key := make([]byte, secretbox.KeySize)
+	rand.Read(key)
+	box, err := secretbox.New(base64.StdEncoding.EncodeToString(key))
+	if err != nil {
+		t.Fatal(err)
+	}
+	e.chat = chattest.New(t)
+	e.chatSvc, err = chat.NewService(st, box, &url.URL{Scheme: "https", Host: "meals.example.com"}, e.chat.Transport())
+	if err != nil {
+		t.Fatal(err)
+	}
+	e.svc, err = shopping.NewService(st, title, e.runner, notifytest.New(t, st), e.chatSvc, logger)
 	if err != nil {
 		t.Fatal(err)
 	}

internal/store/migrate_test.go

@@ -176,8 +176,8 @@ func TestMigrateEmbeddedMigrations(t *testing.T) {
 	if err := Migrate(context.Background(), s.Writer, migrations.FS); err != nil {
 		t.Fatal(err)
 	}
-	if got := versions(migrationRows(t, s)); got != "0000_bootstrap,0001_init,0002_household_settings_updated_by,0003_jobs_status,0004_ai_provider_presets,0005_ai_provider_xai,0006_ai_runs_status,0007_recipe_grounding,0008_dinner_recipe_url,0009_dinner_grounding_error,0010_dinner_grounding_revision,0011_ground_dinner_job_revision,0012_suggestion_name,0013_week_plan_revision,0014_rotation_review_name,0015_google_reconnect_required,0016_shopping_list_untitled" {
-		t.Errorf("versions = %q, want 0000_bootstrap,0001_init,0002_household_settings_updated_by,0003_jobs_status,0004_ai_provider_presets,0005_ai_provider_xai,0006_ai_runs_status,0007_recipe_grounding,0008_dinner_recipe_url,0009_dinner_grounding_error,0010_dinner_grounding_revision,0011_ground_dinner_job_revision,0012_suggestion_name,0013_week_plan_revision,0014_rotation_review_name,0015_google_reconnect_required,0016_shopping_list_untitled", got)
+	if got := versions(migrationRows(t, s)); got != "0000_bootstrap,0001_init,0002_household_settings_updated_by,0003_jobs_status,0004_ai_provider_presets,0005_ai_provider_xai,0006_ai_runs_status,0007_recipe_grounding,0008_dinner_recipe_url,0009_dinner_grounding_error,0010_dinner_grounding_revision,0011_ground_dinner_job_revision,0012_suggestion_name,0013_week_plan_revision,0014_rotation_review_name,0015_google_reconnect_required,0016_shopping_list_untitled,0017_shopping_list_chat_send_unconfirmed" {
+		t.Errorf("versions = %q, want 0000_bootstrap,0001_init,0002_household_settings_updated_by,0003_jobs_status,0004_ai_provider_presets,0005_ai_provider_xai,0006_ai_runs_status,0007_recipe_grounding,0008_dinner_recipe_url,0009_dinner_grounding_error,0010_dinner_grounding_revision,0011_ground_dinner_job_revision,0012_suggestion_name,0013_week_plan_revision,0014_rotation_review_name,0015_google_reconnect_required,0016_shopping_list_untitled,0017_shopping_list_chat_send_unconfirmed", got)
 	}
 }
 
@@ -197,8 +197,8 @@ func TestMigrateBootstrapThenEmbeddedInitApplies(t *testing.T) {
 	if err := Migrate(ctx, s.Writer, migrations.FS); err != nil {
 		t.Fatal(err)
 	}
-	if got := versions(migrationRows(t, s)); got != "0000_bootstrap,0001_init,0002_household_settings_updated_by,0003_jobs_status,0004_ai_provider_presets,0005_ai_provider_xai,0006_ai_runs_status,0007_recipe_grounding,0008_dinner_recipe_url,0009_dinner_grounding_error,0010_dinner_grounding_revision,0011_ground_dinner_job_revision,0012_suggestion_name,0013_week_plan_revision,0014_rotation_review_name,0015_google_reconnect_required,0016_shopping_list_untitled" {
-		t.Errorf("versions = %q, want 0000_bootstrap,0001_init,0002_household_settings_updated_by,0003_jobs_status,0004_ai_provider_presets,0005_ai_provider_xai,0006_ai_runs_status,0007_recipe_grounding,0008_dinner_recipe_url,0009_dinner_grounding_error,0010_dinner_grounding_revision,0011_ground_dinner_job_revision,0012_suggestion_name,0013_week_plan_revision,0014_rotation_review_name,0015_google_reconnect_required,0016_shopping_list_untitled", got)
+	if got := versions(migrationRows(t, s)); got != "0000_bootstrap,0001_init,0002_household_settings_updated_by,0003_jobs_status,0004_ai_provider_presets,0005_ai_provider_xai,0006_ai_runs_status,0007_recipe_grounding,0008_dinner_recipe_url,0009_dinner_grounding_error,0010_dinner_grounding_revision,0011_ground_dinner_job_revision,0012_suggestion_name,0013_week_plan_revision,0014_rotation_review_name,0015_google_reconnect_required,0016_shopping_list_untitled,0017_shopping_list_chat_send_unconfirmed" {
+		t.Errorf("versions = %q, want 0000_bootstrap,0001_init,0002_household_settings_updated_by,0003_jobs_status,0004_ai_provider_presets,0005_ai_provider_xai,0006_ai_runs_status,0007_recipe_grounding,0008_dinner_recipe_url,0009_dinner_grounding_error,0010_dinner_grounding_revision,0011_ground_dinner_job_revision,0012_suggestion_name,0013_week_plan_revision,0014_rotation_review_name,0015_google_reconnect_required,0016_shopping_list_untitled,0017_shopping_list_chat_send_unconfirmed", got)
 	}
 	if !tableExists(t, s, "dinners") {
 		t.Error("table from 0001_init was not created")
@@ -889,3 +889,36 @@ func TestMigrateShoppingListUntitledRefusesUndatedGroup(t *testing.T) {
 		t.Error("shopping_groups_copy left behind")
 	}
 }
+
+// TestMigrateShoppingListChatSendUnconfirmed applies 0017 over a list
+// already sent: it keeps every value, and the list has no send
+// unconfirmed.
+func TestMigrateShoppingListChatSendUnconfirmed(t *testing.T) {
+	ctx := context.Background()
+	s := openTestStore(t)
+	migrateBefore(t, s, "0017")
+	for _, stmt := range []string{
+		`INSERT INTO week_plans (id, week_start, status, created_at, updated_at)
+			VALUES ('plan-1', '2026-10-12', 'synced', 'c', 'u')`,
+		`INSERT INTO shopping_lists (id, week_start, plan_id, title, status, sent_to_chat_at, frozen_at, created_at, updated_at)
+			VALUES ('list-1', '2026-10-12', 'plan-1', 'Noodle week', 'current', 's', NULL, 'c1', 'u1')`,
+	} {
+		if _, err := s.Writer.Exec(stmt); err != nil {
+			t.Fatalf("seed: %v", err)
+		}
+	}
+
+	if err := Migrate(ctx, s.Writer, migrations.FS); err != nil {
+		t.Fatal(err)
+	}
+
+	var got string
+	if err := s.Reader.QueryRowContext(ctx, `SELECT
+		id || '|' || title || '|' || status || '|' || sent_to_chat_at || '|' || COALESCE(chat_send_unconfirmed_at, 'NULL') || '|' || updated_at
+		FROM shopping_lists`).Scan(&got); err != nil {
+		t.Fatal(err)
+	}
+	if want := "list-1|Noodle week|current|s|NULL|u1"; got != want {
+		t.Errorf("shopping list after 0017 = %s, want %s", got, want)
+	}
+}

internal/suggest/batch.go

@@ -10,8 +10,10 @@ import (
 
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/ai/harness"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/ai/skills"
+	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/chat"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/db"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/dinners"
+	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/household"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/jobs"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/recipes"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/store"
@@ -54,7 +56,18 @@ func (r batchResult) PublicJSON() ([]byte, error) { return json.Marshal(r) }
 // recording the batch's end fails, so does the job; when it times out at
 // shutdown, the job is left running and the batch with it, for the next
 // start to fail.
+//
+// A scheduled or manual batch emits new_suggestions, keyed by the batch,
+// in the transaction that first adds Side quests to the deck, so the
+// household is told of every Side quest stored, whether or not the batch
+// then ends done: a later round, or recording the batch's end, may fail.
+// A replenish batch, which tops up the deck as the household swipes, never
+// notifies. See store.
 func (s *Service) runBatch(ctx context.Context, p BatchJob, publish func(batchResult) error) (batchResult, error) {
+	batch, err := db.New(s.st.Reader).GetSuggestionBatch(ctx, p.BatchID)
+	if err != nil {
+		return batchResult{}, fmt.Errorf("suggest: read batch %s: %w", p.BatchID, err)
+	}
 	n, err := db.New(s.st.Writer).StartSuggestionBatch(ctx, db.StartSuggestionBatchParams{
 		UpdatedAt: store.Now().String(),
 		ID:        p.BatchID,
@@ -65,7 +78,7 @@ func (s *Service) runBatch(ctx context.Context, p BatchJob, publish func(batchRe
 	if n == 0 {
 		return batchResult{}, fmt.Errorf("suggest: batch %s is not pending", p.BatchID)
 	}
-	res, err := s.fill(ctx, p.BatchID, publish)
+	res, err := s.fill(ctx, p.BatchID, batch.Trigger != TriggerReplenish, publish)
 	if err == nil {
 		if err := s.finishBatch(ctx, p.BatchID, BatchDone); err != nil {
 			return batchResult{}, err
@@ -86,8 +99,9 @@ func (s *Service) runBatch(ctx context.Context, p BatchJob, publish func(batchRe
 }
 
 // fill does runBatch's work, returning a *jobs.Failure for a failure the
-// household may see.
-func (s *Service) fill(ctx context.Context, batchID string, publish func(batchResult) error) (batchResult, error) {
+// household may see. When notifies is true, store emits new_suggestions
+// with the Side quests it adds.
+func (s *Service) fill(ctx context.Context, batchID string, notifies bool, publish func(batchResult) error) (batchResult, error) {
 	res := batchResult{BatchID: batchID, Stage: StageSuggesting, SuggestionIDs: []string{}}
 	if err := publish(res); err != nil {
 		return batchResult{}, err
@@ -108,6 +122,11 @@ func (s *Service) fill(ctx context.Context, batchID string, publish func(batchRe
 	if err := publish(res); err != nil {
 		return batchResult{}, err
 	}
+	var week *store.LocalDate
+	if notifies {
+		w := household.WeekStart(in.Context.Today)
+		week = &w
+	}
 	left := out.Suggestions
 	for len(res.SuggestionIDs) < BatchSize && len(left) > 0 {
 		round := left[:min(BatchSize-len(res.SuggestionIDs), len(left))]
@@ -117,7 +136,7 @@ func (s *Service) fill(ctx context.Context, batchID string, publish func(batchRe
 			return batchResult{}, err
 		}
 		res.Dropped += len(round) - len(grounded)
-		ids, err := s.store(ctx, batchID, grounded)
+		ids, err := s.store(ctx, batchID, week, grounded)
 		if err != nil {
 			return batchResult{}, err
 		}
@@ -204,8 +223,16 @@ func (s *Service) ground(ctx context.Context, quests []skills.SideQuest) ([]grou
 // repeats passed or a Rotation check dropped, or a Regular it cites renamed
 // or archived. Passed names are read in the same transaction as the store,
 // so a Pass or drop committed before it is never missed.
-func (s *Service) store(ctx context.Context, batchID string, quests []groundedQuest) ([]string, error) {
+//
+// When week is not nil and a Side quest is stored, new_suggestions:{batchID}
+// naming those stored is emitted in the same transaction, for the week
+// starting week, so the Side quests and their notification commit together
+// or not at all: a notification that cannot be stored fails the store, and
+// the batch with it. The event's key makes the first round to store Side
+// quests the one that notifies; a later round's emit stores nothing.
+func (s *Service) store(ctx context.Context, batchID string, week *store.LocalDate, quests []groundedQuest) ([]string, error) {
 	ids := []string{}
+	var stored []string
 	err := s.st.WithTx(ctx, func(tx *sql.Tx) error {
 		q := db.New(tx)
 		existing, err := q.ListUnarchivedDinners(ctx)
@@ -269,12 +296,19 @@ func (s *Service) store(ctx context.Context, batchID string, quests []groundedQu
 			}
 			names = append(names, d.Name)
 			ids = append(ids, id)
+			stored = append(stored, d.Name)
 		}
-		return nil
+		if week == nil || len(stored) == 0 {
+			return nil
+		}
+		return s.notifier.EmitTx(ctx, tx, chat.NewSuggestions(batchID, *week, stored))
 	})
 	if err != nil {
 		return nil, err
 	}
+	if week != nil && len(stored) > 0 {
+		s.notifier.Wake()
+	}
 	return ids, nil
 }
 

internal/suggest/suggest.go

@@ -20,6 +20,7 @@ import (
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/db"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/dinners"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/jobs"
+	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/notify"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/recipes"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/store"
 )
@@ -109,14 +110,16 @@ type Service struct {
 	st       *store.Store
 	grounder *recipes.Grounder
 	suggest  Suggester
+	notifier *notify.Service
 	logger   *slog.Logger
 	batchJob *jobs.Kind[BatchJob]
 }
 
 // NewService returns a service over st that suggests with suggest, grounds
-// with grounder and registers the KindSuggestionBatch job on runner, which
-// must not have started yet.
-func NewService(st *store.Store, grounder *recipes.Grounder, suggest Suggester, runner *jobs.Runner, logger *slog.Logger) (*Service, error) {
+// with grounder, tells the household through notifier, which must be over
+// st, and registers the KindSuggestionBatch job on runner, which must not
+// have started yet.
+func NewService(st *store.Store, grounder *recipes.Grounder, suggest Suggester, runner *jobs.Runner, notifier *notify.Service, logger *slog.Logger) (*Service, error) {
 	switch {
 	case st == nil:
 		return nil, errors.New("suggest: nil store")
@@ -126,10 +129,12 @@ func NewService(st *store.Store, grounder *recipes.Grounder, suggest Suggester,
 		return nil, errors.New("suggest: nil suggester")
 	case runner == nil:
 		return nil, errors.New("suggest: nil job runner")
+	case notifier == nil:
+		return nil, errors.New("suggest: nil notifier")
 	case logger == nil:
 		return nil, errors.New("suggest: nil logger")
 	}
-	s := &Service{st: st, grounder: grounder, suggest: suggest, logger: logger}
+	s := &Service{st: st, grounder: grounder, suggest: suggest, notifier: notifier, logger: logger}
 	kind, err := jobs.Register(runner, KindSuggestionBatch, s.runBatch, Reasons...)
 	if err != nil {
 		return nil, err

internal/suggest/suggest_test.go

@@ -23,6 +23,8 @@ import (
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/gcal"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/household"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/jobs"
+	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/notify"
+	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/notify/notifytest"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/plan"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/recipes"
 	"code.cubecraftlabs.com/Maniacs_Mansion/Meal-Quest/internal/recipes/recipestest"
@@ -121,7 +123,7 @@ func newEnv(t *testing.T) *env {
 	if err != nil {
 		t.Fatal(err)
 	}
-	e.svc, err = suggest.NewService(st, g, suggester, e.runner, logger)
+	e.svc, err = suggest.NewService(st, g, suggester, e.runner, notifytest.New(t, st), logger)
 	if err != nil {
 		t.Fatal(err)
 	}
@@ -401,6 +403,151 @@ func TestBatchStoresGroundedSideQuests(t *testing.T) {
 	}
 }
 
+// TestBatchEmitsNewSuggestions: a scheduled or manual batch that adds Side
+// quests stores new_suggestions keyed by the batch, naming them; a
+// replenish batch, or one that adds none, stores nothing.
+func TestBatchEmitsNewSuggestions(t *testing.T) {
+	for _, tc := range []struct {
+		trigger string
+		grounds bool
+		notify  bool
+	}{
+		{suggest.TriggerScheduled, true, true},
+		{suggest.TriggerManual, true, true},
+		{suggest.TriggerReplenish, true, false},
+		{suggest.TriggerManual, false, false},
+	} {
+		t.Run(fmt.Sprintf("%s grounds %v", tc.trigger, tc.grounds), func(t *testing.T) {
+			e := newEnv(t)
+			e.start(t)
+			if tc.grounds {
+				e.recipe(t, "Chicken Shawarma Bowls")
+				e.recipe(t, "Chili Verde")
+			}
+			e.reply(
+				sideQuest("Chicken Shawarma Bowls", "Spiced chicken, like your Chicken Fajitas.", "Chicken Fajitas"),
+				sideQuest("Chili Verde", "Your Beef Chili gone green.", "Beef Chili"),
+			)
+			b, err := e.svc.StartBatch(t.Context(), tc.trigger)
+			if err != nil {
+				t.Fatal(err)
+			}
+			if job := e.waitJob(t, b.JobID); job.Status != jobs.StatusSucceeded {
+				t.Fatalf("batch job %s", job.Status)
+			}
+			rows := notifytest.Rows(t, e.st, notify.NewSuggestions)
+			if !tc.notify {
+				if len(rows) != 0 {
+					t.Errorf("new_suggestions rows = %+v, want none", rows)
+				}
+				return
+			}
+			if len(rows) != 1 {
+				t.Fatalf("new_suggestions rows = %+v, want one on push", rows)
+			}
+			r := rows[0]
+			if r.Key != "new_suggestions:"+b.ID || r.Channel != notify.ChannelPush || r.Payload.URL != "/discover" ||
+				r.Payload.Title != "New Side quests are in" || r.Payload.Body != "Chicken Shawarma Bowls, Chili Verde" || r.Payload.Week == "" {
+				t.Errorf("new_suggestions row = %+v, want key new_suggestions:%s naming the Side quests, /discover", r, b.ID)
+			}
+		})
+	}
+}
+
+// TestBatchNotifiesAsSideQuestsAreStored: new_suggestions is stored with
+// the first round to add Side quests, so a batch whose later round fails
+// still tells the household of those in the deck, once; a later round that
+// succeeds adds no second notification; a replenish batch notifies nothing.
+func TestBatchNotifiesAsSideQuestsAreStored(t *testing.T) {
+	for _, tc := range []struct {
+		trigger   string
+		lastFails bool
+		notify    bool
+	}{
+		{suggest.TriggerScheduled, true, true},
+		{suggest.TriggerManual, true, true},
+		{suggest.TriggerManual, false, true},
+		{suggest.TriggerReplenish, true, false},
+	} {
+		t.Run(fmt.Sprintf("%s last round fails %v", tc.trigger, tc.lastFails), func(t *testing.T) {
+			e := newEnv(t)
+			e.start(t)
+			// The first round grounds BatchSize Side quests but B; the
+			// second round grounds F.
+			var quests []string
+			for i := range suggest.BatchSize + 1 {
+				name := fmt.Sprintf("Fajita Dish %c", 'A'+i)
+				e.search.Results[name] = nil
+				if i != 1 {
+					e.recipe(t, name)
+				}
+				quests = append(quests, sideQuest(name, "Like your Chicken Fajitas.", "Chicken Fajitas"))
+			}
+			e.reply(quests...)
+			if tc.lastFails {
+				if _, err := e.st.Writer.ExecContext(t.Context(), `CREATE TRIGGER refuse_f BEFORE INSERT ON dinners WHEN NEW.name = 'Fajita Dish F' BEGIN SELECT RAISE(ABORT, 'F refused'); END`); err != nil {
+					t.Fatal(err)
+				}
+			}
+
+			b, err := e.svc.StartBatch(t.Context(), tc.trigger)
+			if err != nil {
+				t.Fatal(err)
+			}
+			job := e.waitJob(t, b.JobID)
+			want, deck := jobs.StatusSucceeded, suggest.BatchSize
+			if tc.lastFails {
+				want, deck = jobs.StatusFailed, suggest.BatchSize-1
+			}
+			if job.Status != want {
+				t.Fatalf("batch job %s, want %s", job.Status, want)
+			}
+			if got := e.deckNames(t); len(got) != deck {
+				t.Fatalf("deck = %v, want %d Side quests", got, deck)
+			}
+			rows := notifytest.Rows(t, e.st, notify.NewSuggestions)
+			if !tc.notify {
+				if len(rows) != 0 {
+					t.Errorf("new_suggestions rows = %+v, want none", rows)
+				}
+				return
+			}
+			if len(rows) != 1 || rows[0].Key != "new_suggestions:"+b.ID ||
+				rows[0].Payload.Body != "Fajita Dish A, Fajita Dish C, Fajita Dish D + 1 more" {
+				t.Errorf("new_suggestions rows = %+v, want one keyed by batch %s naming the first round", rows, b.ID)
+			}
+		})
+	}
+}
+
+// TestBatchFailsWhenItsNotificationCannotBeStored: Side quests are stored
+// only with their notification, so a notification that cannot be stored
+// fails the batch with an empty deck rather than leaving Side quests the
+// household is never told of.
+func TestBatchFailsWhenItsNotificationCannotBeStored(t *testing.T) {
+	e := newEnv(t)
+	e.start(t)
+	e.recipe(t, "Chili Verde")
+	e.reply(sideQuest("Chili Verde", "Your Beef Chili gone green.", "Beef Chili"))
+	if _, err := e.st.Writer.ExecContext(t.Context(), `CREATE TRIGGER refuse_outbox BEFORE INSERT ON notification_outbox BEGIN SELECT RAISE(ABORT, 'outbox refused'); END`); err != nil {
+		t.Fatal(err)
+	}
+
+	b, err := e.svc.StartBatch(t.Context(), suggest.TriggerManual)
+	if err != nil {
+		t.Fatal(err)
+	}
+	if job := e.waitJob(t, b.JobID); job.Status != jobs.StatusFailed {
+		t.Fatalf("batch job %s, want failed", job.Status)
+	}
+	if got := e.batchStatus(t, b.ID); got != suggest.BatchFailed {
+		t.Errorf("batch status = %s, want failed", got)
+	}
+	if got := e.deckNames(t); len(got) != 0 {
+		t.Errorf("deck = %v with no notification stored, want empty", got)
+	}
+}
+
 func TestBatchKeepsAtMostBatchSize(t *testing.T) {
 	e := newEnv(t)
 	e.start(t)
@@ -929,7 +1076,7 @@ func TestLaterBatchNeverResuggestsRenamedDrop(t *testing.T) {
 	fail := func(context.Context, string, skills.WeekRequest) (skills.Week, error) {
 		return skills.Week{}, errors.New("no draft in this test")
 	}
-	planSvc, err := plan.NewService(e.st, fail, e.runner, noCalendar{}, &url.URL{Scheme: "https", Host: "meals.example.com"}, logger)
+	planSvc, err := plan.NewService(e.st, fail, e.runner, noCalendar{}, notifytest.New(t, e.st), &url.URL{Scheme: "https", Host: "meals.example.com"}, logger)
 	if err != nil {
 		t.Fatal(err)
 	}
@@ -1151,6 +1298,10 @@ func TestBatchJobFailsWhenRecordingItsEndFails(t *testing.T) {
 	if got := e.batchStatus(t, b.ID); got != suggest.BatchFailed {
 		t.Errorf("batch status = %s with its job failed, want failed", got)
 	}
+	// Its Side quests stay in the deck, and the household was told of them.
+	if rows := notifytest.Rows(t, e.st, notify.NewSuggestions); len(rows) != 1 || rows[0].Key != "new_suggestions:"+b.ID || rows[0].Payload.Body != "Chili Verde" {
+		t.Errorf("new_suggestions rows of a batch whose end was not recorded = %+v, want one naming Chili Verde", rows)
+	}
 }
 
 func TestBatchRecoversWhenRecordingItsEndAndItsJobsEndFail(t *testing.T) {
@@ -1284,7 +1435,7 @@ func TestBlockedBatchEndDoesNotHoldShutdown(t *testing.T) {
 	refuse := func(context.Context, string, skills.SideQuestsRequest) (skills.SideQuests, error) {
 		return skills.SideQuests{}, errors.New("not wanted")
 	}
-	svc, err := suggest.NewService(e.st, e.grounder, refuse, next, logger)
+	svc, err := suggest.NewService(e.st, e.grounder, refuse, next, notifytest.New(t, e.st), logger)
 	if err != nil {
 		t.Fatal(err)
 	}

migrations/0017_shopping_list_chat_send_unconfirmed.sql

@@ -0,0 +1,10 @@
+-- 0017_shopping_list_chat_send_unconfirmed: a send of a Supply run to
+-- Google Chat is recorded as begun, in chat_send_unconfirmed_at, before it
+-- is posted, and cleared when Google Chat's answer is known: with
+-- sent_to_chat_at when it accepted the post, alone when it refused it. A
+-- value left behind (Google Chat did not answer, the process stopped, or
+-- recording the answer failed) means the post may or may not have been
+-- made, so it is never posted again without resend. Existing rows have no
+-- send under way.
+
+ALTER TABLE shopping_lists ADD COLUMN chat_send_unconfirmed_at TEXT;

migrations/queries/shopping.sql

@@ -89,6 +89,27 @@ UPDATE shopping_lists
 SET title = ?, updated_at = ?
 WHERE id = ? AND title IS NULL AND status = 'current' AND frozen_at IS NULL;
 
+-- name: BeginShoppingListChatSend :execrows
+-- Records a send of list id to Google Chat begun at
+-- chat_send_unconfirmed_at, before it is posted, unless the list is frozen
+-- into the Supply archive.
+UPDATE shopping_lists
+SET chat_send_unconfirmed_at = ?, updated_at = ?
+WHERE id = ? AND status = 'current' AND frozen_at IS NULL;
+
+-- name: MarkShoppingListSentToChat :execrows
+-- Records list id sent to Google Chat at sent_to_chat_at, its send
+-- confirmed, unless it is frozen into the Supply archive.
+UPDATE shopping_lists
+SET sent_to_chat_at = ?, chat_send_unconfirmed_at = NULL, updated_at = ?
+WHERE id = ? AND status = 'current' AND frozen_at IS NULL;
+
+-- name: ClearShoppingListChatSend :execrows
+-- Clears the send of list id begun, once Google Chat refused it.
+UPDATE shopping_lists
+SET chat_send_unconfirmed_at = NULL, updated_at = ?
+WHERE id = ?;
+
 -- name: FreezeShoppingList :execrows
 -- Freezes list id into the Supply archive at frozen_at, unless it is
 -- frozen already.

migrations/queries/suggestions.sql

@@ -26,6 +26,11 @@ WHERE kind = sqlc.arg(kind)
 ORDER BY id
 LIMIT 1;
 
+-- name: GetSuggestionBatch :one
+-- Batch id. Returns sql.ErrNoRows when there is none.
+SELECT * FROM suggestion_batches
+WHERE id = ?;
+
 -- name: StartSuggestionBatch :execrows
 -- Marks a pending batch running; a batch in any other status is left as
 -- it is (0 rows).

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.module.css

@@ -258,75 +258,10 @@
   color: var(--color-neutral-700);
 }
 
-/* An action with nothing behind it yet (Send to Google Chat until Feature
-   19): it keeps focus, so hovering, tapping or focusing it shows the
-   tooltip. */
-.unavailable {
-  position: relative;
-  display: flex;
-  flex-direction: column;
-}
-
 .pushButton {
   min-height: 50px;
 }
 
-.unavailable [aria-disabled='true'] {
-  opacity: 0.45;
-  cursor: not-allowed;
-}
-
-/* Unavailable, it neither darkens nor presses. */
-.unavailable .primary[aria-disabled='true']:hover,
-.unavailable .primary[aria-disabled='true']:active {
-  background: var(--color-accent);
-  transform: none;
-}
-
-.unavailable .outline[aria-disabled='true']:hover,
-.unavailable .outline[aria-disabled='true']:active {
-  background: transparent;
-  transform: none;
-}
-
-.hint {
-  position: absolute;
-  bottom: calc(100% + 8px);
-  left: 50%;
-  transform: translateX(-50%);
-  width: max-content;
-  max-width: 100%;
-  padding: 8px 12px;
-  border-radius: var(--radius-md);
-  background: var(--color-text);
-  color: var(--color-bg);
-  font-family: var(--font-body);
-  font-size: 13px;
-  line-height: 1.4;
-  text-align: center;
-  box-shadow: var(--shadow-md);
-  visibility: hidden;
-  pointer-events: none;
-}
-
-/* In the plan manager's header the tooltip opens below, at the action's
-   right edge. */
-.below .hint {
-  top: calc(100% + 8px);
-  bottom: auto;
-  left: auto;
-  right: 0;
-  transform: none;
-  width: 240px;
-  max-width: none;
-  z-index: 1;
-}
-
-.unavailable:hover .hint,
-.unavailable [aria-disabled='true']:focus + .hint {
-  visibility: visible;
-}
-
 /* The plan manager's header: kicker and title beside the week buttons, over
    the sync status and the actions. */
 .wideHeader {

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/plan/PlanPage.tsx

@@ -1,6 +1,6 @@
 import { useQueryClient } from '@tanstack/react-query'
 import { CalendarDays, Check, ChevronLeft, ChevronRight, Plus, RefreshCw, ShoppingCart } from 'lucide-react'
-import { useEffect, useId, useMemo, useState, type ReactNode } from 'react'
+import { useEffect, useMemo, useState } from 'react'
 import { Link } from 'react-router'
 import { ApiError, useJob } from '../api/index.ts'
 import { QUEST_LOG_KEY } from '../discover/api.ts'
@@ -9,7 +9,7 @@ import { methodLabels } from '../settings/RegularsSettingsPage.tsx'
 import { formatClockTime, useHouseholdSettings } from '../settings/api.ts'
 import { supplyRunScreen, useGenerateSupplyRun, useSupplyRun } from '../shopping/api.ts'
 import { useBreakpoint, type Breakpoint } from '../shell/useBreakpoint.ts'
-import { Button, type ButtonVariant } from '../ui/Button.tsx'
+import { Button } from '../ui/Button.tsx'
 import buttonStyles from '../ui/Button.module.css'
 import { EmptyState } from '../ui/EmptyState.tsx'
 import { ErrorBanner } from '../ui/ErrorBanner.tsx'
@@ -672,40 +672,6 @@ function PushFailure({ error, cached, onRetry }: { error: Error; cached: boolean
   )
 }
 
-// Unavailable is an action with nothing behind it yet (Send to Google
-// Chat): it stays focusable, so a tap or focus shows the tooltip saying
-// why, above it or, at the top of the page, below.
-export function Unavailable({
-  hint,
-  variant = 'primary',
-  below = false,
-  className,
-  children,
-}: {
-  hint: string
-  variant?: ButtonVariant
-  below?: boolean
-  className?: string
-  children: ReactNode
-}) {
-  const hintId = useId()
-  return (
-    <div className={[styles.unavailable, below && styles.below].filter(Boolean).join(' ')}>
-      <Button
-        variant={variant}
-        className={[className, styles[variant]].filter(Boolean).join(' ')}
-        aria-disabled="true"
-        aria-describedby={hintId}
-      >
-        {children}
-      </Button>
-      <span id={hintId} role="tooltip" className={styles.hint}>
-        {hint}
-      </span>
-    </div>
-  )
-}
-
 // PlanPage is the Draft board on the week chosen with the previous / next
 // week buttons: mock 1f on mobile; from tablet up the plan manager, with the
 // Quest log as a strip under the grid on tablet (2c) and the Quest log and

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

@@ -13,6 +13,7 @@ import { sentAt, SupplyRunPage } from './SupplyRunPage.tsx'
 
 const THIS_WEEK = '/api/v1/shopping/2026-10-05'
 const GENERATE = `${THIS_WEEK}/generate`
+const SEND_CHAT = `${THIS_WEEK}/send-chat`
 const ITEM = (id: string) => `/api/v1/shopping/items/${id}`
 
 type Item = { id: string; name: string; qty: string | null; needed: boolean }
@@ -52,6 +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,
@@ -372,19 +374,122 @@ describe('SupplyRunPage', () => {
     expect(archive).toHaveAttribute('href', '/plan/shopping/archive')
     expect(archive).toHaveClass(buttonStyles.outline!)
 
-    // Send to Google Chat waits for Feature 19: primary, unavailable, and
-    // its tooltip says so. Pressing it sends nothing.
-    const send = screen.getByRole('button', { name: 'Send to Google Chat' })
+    // Already sent, the primary action sends it again.
+    const send = screen.getByRole('button', { name: 'Send again' })
     expect(send).toHaveClass(buttonStyles.primary!)
-    expect(send).toHaveAttribute('aria-disabled', 'true')
-    expect(send).toHaveAccessibleDescription('Sending the shopping list to Google Chat arrives in a later update.')
-    fireEvent.click(send)
+    expect(send).toBeEnabled()
     expect(writes(fetchMock)).toEqual([])
 
     expect(screen.getByText('Sent to Google Chat · Sat 8:00 am')).toBeInTheDocument()
     expect(screen.queryByRole('link', { name: 'Supply archive' })).not.toBeInTheDocument()
   })
 
+  it('sends the list to Google Chat once and shows when it was sent', async () => {
+    mockViewport(1180)
+    const sent = deferred()
+    const fetchMock = stubServer({
+      [`GET ${THIS_WEEK}`]: () => jsonResponse(200, supplyRun()),
+      [`POST ${SEND_CHAT}`]: () => sent.response,
+    })
+    await renderPage()
+
+    await screen.findByText('4 / 6')
+    expect(screen.queryByText(/Sent to Google Chat ·/)).not.toBeInTheDocument()
+    fireEvent.click(screen.getByRole('button', { name: 'Send to Google Chat' }))
+
+    const sending = await screen.findByRole('button', { name: 'Sending…' })
+    expect(sending).toBeDisabled()
+    expect(writes(fetchMock)).toEqual([`POST ${SEND_CHAT} {"resend":false}`])
+    // Saturday Oct 10, 8:00 am in New York.
+    sent.send(jsonResponse(200, supplyRun({ sent_to_chat_at: '2026-10-10T12:00:00Z' })))
+
+    expect(await screen.findByText('Sent to Google Chat · Sat 8:00 am')).toBeInTheDocument()
+    expect(screen.getByRole('button', { name: 'Send again' })).toBeEnabled()
+    expect(screen.queryByRole('alert')).not.toBeInTheDocument()
+  })
+
+  it('sends a list already sent again with resend', async () => {
+    mockViewport(1440)
+    const fetchMock = stubServer({
+      [`GET ${THIS_WEEK}`]: () => jsonResponse(200, supplyRun({ sent_to_chat_at: '2026-10-10T12:00:00Z' })),
+      [`POST ${SEND_CHAT}`]: () => jsonResponse(200, supplyRun({ sent_to_chat_at: '2026-10-10T16:30:00Z' })),
+    })
+    await renderPage()
+
+    fireEvent.click(await screen.findByRole('button', { name: 'Send again' }))
+
+    expect(await screen.findByText('Sent to Google Chat · Sat 12:30 pm')).toBeInTheDocument()
+    expect(writes(fetchMock)).toEqual([`POST ${SEND_CHAT} {"resend":true}`])
+  })
+
+  it('says why a send to Google Chat failed, and retries it', async () => {
+    mockViewport(1180)
+    const answers = [
+      () => errorResponse(409, 'not_configured'),
+      () => jsonResponse(200, supplyRun({ sent_to_chat_at: '2026-10-10T12:00:00Z' })),
+    ]
+    const fetchMock = stubServer({
+      [`GET ${THIS_WEEK}`]: () => jsonResponse(200, supplyRun()),
+      [`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. not_configured message")
+    expect(screen.queryByText(/Sent to Google Chat ·/)).not.toBeInTheDocument()
+    expect(screen.getByRole('button', { name: 'Send to Google Chat' })).toBeEnabled()
+
+    fireEvent.click(within(alert).getByRole('button', { name: 'Retry' }))
+    expect(await screen.findByText('Sent to Google Chat · Sat 8:00 am')).toBeInTheDocument()
+    expect(screen.queryByRole('alert')).not.toBeInTheDocument()
+    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

@@ -1,10 +1,11 @@
 import { Archive, Check, CloudUpload, MessageSquare } from 'lucide-react'
 import { useState } from 'react'
 import { Link, useSearchParams } from 'react-router'
-import { Unavailable } from '../plan/PlanPage.tsx'
 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'
 import buttonStyles from '../ui/Button.module.css'
 import { Checkbox } from '../ui/Checkbox.tsx'
 import { EmptyState } from '../ui/EmptyState.tsx'
@@ -14,6 +15,7 @@ import { Skeleton } from '../ui/Skeleton.tsx'
 import { Tag } from '../ui/Tag.tsx'
 import {
   useGenerateSupplyRun,
+  useSendToChat,
   useSupplyRun,
   useToggles,
   WEEK_PARAM,
@@ -27,10 +29,6 @@ import styles from './SupplyRunPage.module.css'
 // SUPPLY_ARCHIVE is the Supply archive screen.
 export const SUPPLY_ARCHIVE = '/plan/shopping/archive'
 
-// CHAT_HINT is why Send to Google Chat is unavailable.
-// TODO(Feature 19): send the Supply run to Google Chat once it is built.
-const CHAT_HINT = 'Sending the shopping list to Google Chat arrives in a later update.'
-
 // sentAt is when the Supply run was sent to Google Chat as its status line
 // says it, in the household's zone: "Sat 8:00 am".
 export function sentAt(at: Date, timezone: string): string {
@@ -104,6 +102,29 @@ 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, 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}>
+      <Icon icon={MessageSquare} size="inline" />
+      {pending ? 'Sending…' : sent ? 'Send again' : 'Send to Google Chat'}
+    </Button>
+  )
+}
+
 // ArchiveLink opens the Supply archive: an outline action from tablet up, a
 // grape link on mobile.
 function ArchiveLink({ layout }: { layout: Breakpoint }) {
@@ -120,13 +141,22 @@ 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. 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.
 function SupplyRunList({ weekStart, timezone, layout, readOnly }: WeekProps) {
   const toggles = useToggles(weekStart)
+  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
@@ -155,12 +185,7 @@ function SupplyRunList({ weekStart, timezone, layout, readOnly }: WeekProps) {
         {wide && (
           <div className={styles.actions}>
             <ArchiveLink layout={layout} />
-            {!viewOnly && (
-              <Unavailable hint={CHAT_HINT} below className={styles.action}>
-                <Icon icon={MessageSquare} size="inline" />
-                Send to Google Chat
-              </Unavailable>
-            )}
+            {!viewOnly && <SendToChat sent={resend} pending={send.isPending} onSend={() => send.mutate(resend)} />}
           </div>
         )}
       </header>
@@ -170,7 +195,13 @@ function SupplyRunList({ weekStart, timezone, layout, readOnly }: WeekProps) {
           {failed.error.message}
         </ErrorBanner>
       )}
+      {send.isError && !viewOnly && (
+        <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>
       ) : (
@@ -183,6 +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)),
   }
@@ -206,6 +210,27 @@ 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, 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()
+  return useMutation({
+    mutationFn: async (resend: boolean): Promise<SupplyRun> => {
+      const path = `${supplyRunPath(weekStart)}/send-chat`
+      return parseSupplyRun(`POST ${path}`, weekStart, await apiFetch<unknown>(path, { method: 'POST', body: { resend } }))
+    },
+    onSuccess: (run) => {
+      queryClient.setQueryData<SupplyRun | null>(supplyRunKey(weekStart), run)
+    },
+    onError: () => queryClient.invalidateQueries({ queryKey: supplyRunKey(weekStart) }),
+  })
+}
+
 // Toggle is one item marked to buy (needed) or "have it" (not needed).
 export type Toggle = { id: string; needed: boolean }
 

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: [
       {