fix: resolve bugs in chatd streaming system (#22720)

Split from #22693 per review feedback.

Fixes multiple bugs in coderd/chatd and sub-packages including race
conditions, transaction safety, stream buffer bounds, retry limits, and
enterprise relay improvements.

See commit message for full list.

coderd/chatd/chatd.go

@@ -43,6 +43,10 @@ const (
 	instructionCacheTTL          = 5 * time.Minute
 	chatHeartbeatInterval        = 30 * time.Second
 	maxChatSteps                 = 1200
+	// maxStreamBufferSize caps the number of events buffered
+	// per chat during a single LLM step. When exceeded the
+	// oldest event is evicted so memory stays bounded.
+	maxStreamBufferSize = 10000
 
 	// staleRecoveryIntervalDivisor determines how often the stale
 	// recovery loop runs relative to the stale threshold. A value
@@ -104,12 +108,14 @@ type AgentConnFunc func(ctx context.Context, agentID uuid.UUID) (workspacesdk.Ag
 //   - ctx: subscription lifetime context (canceled on unsubscribe).
 //   - params: all state needed to build the merged stream.
 //
-// Returns the merged event channel and a cleanup function.
+// Returns the merged event channel. Cleanup is driven by ctx
+// cancellation — the merge goroutine tears down all relay state
+// in its defer when ctx is done.
 // Set by enterprise for HA deployments. Nil in AGPL single-replica.
 type SubscribeFn func(
 	ctx context.Context,
 	params SubscribeFnParams,
-) (<-chan codersdk.ChatStreamEvent, func())
+) <-chan codersdk.ChatStreamEvent
 
 // StatusNotification informs the enterprise relay manager of chat
 // status changes so it can open or close relay connections.
@@ -521,7 +527,7 @@ func (p *Server) EditMessage(
 		return EditMessageResult{}, txErr
 	}
 
-	p.publishMessage(opts.ChatID, result.Message)
+	p.publishEditedMessage(opts.ChatID, result.Message)
 	p.publishEvent(opts.ChatID, codersdk.ChatStreamEvent{
 		Type:           codersdk.ChatStreamEventTypeQueueUpdate,
 		QueuedMessages: []codersdk.ChatQueuedMessage{},
@@ -554,6 +560,26 @@ func (p *Server) ArchiveChat(ctx context.Context, chatID uuid.UUID) error {
 	return nil
 }
 
+// UnarchiveChat unarchives a chat and publishes a created event so sidebar
+// clients are notified that the chat has reappeared.
+func (p *Server) UnarchiveChat(ctx context.Context, chatID uuid.UUID) error {
+	if chatID == uuid.Nil {
+		return xerrors.New("chat_id is required")
+	}
+
+	chat, err := p.db.GetChatByID(ctx, chatID)
+	if err != nil {
+		return xerrors.Errorf("get chat: %w", err)
+	}
+
+	if err := p.db.UnarchiveChatByID(ctx, chatID); err != nil {
+		return xerrors.Errorf("unarchive chat: %w", err)
+	}
+
+	p.publishChatPubsubEvent(chat, coderdpubsub.ChatEventKindCreated)
+	return nil
+}
+
 // DeleteQueued removes a queued user message and publishes the queue update.
 func (p *Server) DeleteQueued(
 	ctx context.Context,
@@ -564,28 +590,51 @@ func (p *Server) DeleteQueued(
 		return xerrors.New("chat_id is required")
 	}
 
-	err := p.db.DeleteChatQueuedMessage(ctx, database.DeleteChatQueuedMessageParams{
-		ID:     queuedMessageID,
-		ChatID: chatID,
-	})
-	if err != nil {
-		return xerrors.Errorf("delete queued message: %w", err)
-	}
+	var queuedMessages []database.ChatQueuedMessage
+	var queueLoadedOK bool
+
+	txErr := p.db.InTx(func(tx database.Store) error {
+		// Lock the chat row to prevent processChat from
+		// auto-promoting a message the user intended to delete.
+		if _, err := tx.GetChatByIDForUpdate(ctx, chatID); err != nil {
+			return xerrors.Errorf("lock chat: %w", err)
+		}
+
+		err := tx.DeleteChatQueuedMessage(ctx, database.DeleteChatQueuedMessageParams{
+			ID:     queuedMessageID,
+			ChatID: chatID,
+		})
+		if err != nil {
+			return xerrors.Errorf("delete queued message: %w", err)
+		}
+
+		var err2 error
+		queuedMessages, err2 = tx.GetChatQueuedMessages(ctx, chatID)
+		if err2 != nil {
+			p.logger.Warn(ctx, "failed to load queued messages after delete",
+				slog.F("chat_id", chatID),
+				slog.F("queued_message_id", queuedMessageID),
+				slog.Error(err2),
+			)
+			// Non-fatal: the delete succeeded, so we still commit.
+			return nil
+		}
+		queueLoadedOK = true
 
-	queuedMessages, err := p.db.GetChatQueuedMessages(ctx, chatID)
-	if err != nil {
-		p.logger.Warn(ctx, "failed to load queued messages after delete",
-			slog.F("chat_id", chatID),
-			slog.F("queued_message_id", queuedMessageID),
-			slog.Error(err),
-		)
 		return nil
+	}, nil)
+	if txErr != nil {
+		return txErr
 	}
 
-	p.publishEvent(chatID, codersdk.ChatStreamEvent{
-		Type:           codersdk.ChatStreamEventTypeQueueUpdate,
-		QueuedMessages: db2sdk.ChatQueuedMessages(queuedMessages),
-	})
+	if queueLoadedOK {
+		p.publishEvent(chatID, codersdk.ChatStreamEvent{
+			Type:           codersdk.ChatStreamEventTypeQueueUpdate,
+			QueuedMessages: db2sdk.ChatQueuedMessages(queuedMessages),
+		})
+	}
+	// Always notify subscribers so they can re-fetch, even if we
+	// failed to load the updated queue payload above.
 	p.publishChatStreamNotify(chatID, coderdpubsub.ChatStreamNotifyMessage{
 		QueueUpdate: true,
 	})
@@ -681,6 +730,7 @@ func (p *Server) PromoteQueued(
 	})
 	p.publishMessage(opts.ChatID, promoted)
 	p.publishStatus(opts.ChatID, updatedChat.Status, updatedChat.WorkerID)
+	p.publishChatPubsubEvent(updatedChat, coderdpubsub.ChatEventKindStatusChange)
 
 	return result, nil
 }
@@ -964,9 +1014,15 @@ func (p *Server) publishToStream(chatID uuid.UUID, event codersdk.ChatStreamEven
 	state := p.streamStateLocked(chatID)
 	if event.Type == codersdk.ChatStreamEventTypeMessagePart {
 		if !state.buffering {
+			p.cleanupStreamIfIdleLocked(chatID, state)
 			p.streamMu.Unlock()
 			return
 		}
+		if len(state.buffer) >= maxStreamBufferSize {
+			p.logger.Warn(context.Background(), "chat stream buffer full, dropping oldest event",
+				slog.F("chat_id", chatID), slog.F("buffer_size", len(state.buffer)))
+			state.buffer = state.buffer[1:]
+		}
 		state.buffer = append(state.buffer, event)
 	}
 	subscribers := make([]chan codersdk.ChatStreamEvent, 0, len(state.subscribers))
@@ -983,6 +1039,15 @@ func (p *Server) publishToStream(chatID uuid.UUID, event codersdk.ChatStreamEven
 				slog.F("chat_id", chatID), slog.F("type", event.Type))
 		}
 	}
+
+	// Clean up the stream entry if it was created by
+	// streamStateLocked but has no subscribers and is not
+	// actively buffering (e.g. publish with no watchers).
+	p.streamMu.Lock()
+	if cur, ok := p.chatStreams[chatID]; ok {
+		p.cleanupStreamIfIdleLocked(chatID, cur)
+	}
+	p.streamMu.Unlock()
 }
 
 func (p *Server) subscribeToStream(chatID uuid.UUID) (
@@ -1055,73 +1120,6 @@ func (p *Server) Subscribe(
 	// Subscribe to local stream for message_parts (ephemeral).
 	localSnapshot, localParts, localCancel := p.subscribeToStream(chatID)
 
-	// Build initial snapshot synchronously.
-	initialSnapshot := make([]codersdk.ChatStreamEvent, 0)
-	// Add local message_parts to snapshot
-	for _, event := range localSnapshot {
-		if event.Type == codersdk.ChatStreamEventTypeMessagePart {
-			initialSnapshot = append(initialSnapshot, event)
-		}
-	}
-
-	// Load initial messages from DB. When afterMessageID > 0 the
-	// caller already has messages up to that ID (e.g. from the REST
-	// endpoint), so we only fetch newer ones to avoid sending
-	// duplicate data.
-	messages, err := p.db.GetChatMessagesByChatID(ctx, database.GetChatMessagesByChatIDParams{
-		ChatID:  chatID,
-		AfterID: afterMessageID,
-	})
-	if err == nil {
-		for _, msg := range messages {
-			sdkMsg := db2sdk.ChatMessage(msg)
-			initialSnapshot = append(initialSnapshot, codersdk.ChatStreamEvent{
-				Type:    codersdk.ChatStreamEventTypeMessage,
-				ChatID:  chatID,
-				Message: &sdkMsg,
-			})
-		}
-	}
-
-	// Load initial queue.
-	queued, err := p.db.GetChatQueuedMessages(ctx, chatID)
-	if err == nil && len(queued) > 0 {
-		initialSnapshot = append(initialSnapshot, codersdk.ChatStreamEvent{
-			Type:           codersdk.ChatStreamEventTypeQueueUpdate,
-			ChatID:         chatID,
-			QueuedMessages: db2sdk.ChatQueuedMessages(queued),
-		})
-	}
-
-	// Get initial chat state to determine if we need a relay.
-	chat, err := p.db.GetChatByID(ctx, chatID)
-
-	// Include the current chat status in the snapshot so the
-	// frontend can gate message_part processing correctly from
-	// the very first batch, without waiting for a separate REST
-	// query.
-	if err == nil {
-		statusEvent := codersdk.ChatStreamEvent{
-			Type:   codersdk.ChatStreamEventTypeStatus,
-			ChatID: chatID,
-			Status: &codersdk.ChatStreamStatus{
-				Status: codersdk.ChatStatus(chat.Status),
-			},
-		}
-		// Prepend so the frontend sees the status before any
-		// message_part events.
-		initialSnapshot = append([]codersdk.ChatStreamEvent{statusEvent}, initialSnapshot...)
-	}
-
-	// Track the last message ID we've seen for DB queries.
-	// Initialize from afterMessageID so that when the caller passes
-	// afterMessageID > 0 but no new messages exist yet, the first
-	// pubsub catch-up doesn't re-fetch already-seen messages.
-	lastMessageID := afterMessageID
-	if len(messages) > 0 {
-		lastMessageID = messages[len(messages)-1].ID
-	}
-
 	// Merge all event sources.
 	mergedCtx, mergedCancel := context.WithCancel(ctx)
 	mergedEvents := make(chan codersdk.ChatStreamEvent, 128)
@@ -1132,6 +1130,10 @@ func (p *Server) Subscribe(
 	// Subscribe to pubsub for durable events (status, messages,
 	// queue updates, errors). When pubsub is nil (e.g. in-memory
 	// single-instance) we skip this and deliver all local events.
+	//
+	// This MUST happen before the DB queries below so that any
+	// notification published between the query and the subscription
+	// is not lost (subscribe-first-then-query pattern).
 	var notifications <-chan coderdpubsub.ChatStreamNotifyMessage
 	var errCh <-chan error
 	if p.pubsub != nil {
@@ -1175,18 +1177,115 @@ func (p *Server) Subscribe(
 		}
 	}
 
+	// Build initial snapshot synchronously. The pubsub subscription
+	// is already active so no notifications can be lost during this
+	// window.
+	initialSnapshot := make([]codersdk.ChatStreamEvent, 0)
+	// Add local message_parts to snapshot
+	for _, event := range localSnapshot {
+		if event.Type == codersdk.ChatStreamEventTypeMessagePart {
+			initialSnapshot = append(initialSnapshot, event)
+		}
+	}
+
+	// Load initial messages from DB. When afterMessageID > 0 the
+	// caller already has messages up to that ID (e.g. from the REST
+	// endpoint), so we only fetch newer ones to avoid sending
+	// duplicate data.
+	messages, err := p.db.GetChatMessagesByChatID(ctx, database.GetChatMessagesByChatIDParams{
+		ChatID:  chatID,
+		AfterID: afterMessageID,
+	})
+	if err != nil {
+		p.logger.Error(ctx, "failed to load initial chat messages",
+			slog.Error(err),
+			slog.F("chat_id", chatID),
+		)
+		initialSnapshot = append(initialSnapshot, codersdk.ChatStreamEvent{
+			Type:   codersdk.ChatStreamEventTypeError,
+			ChatID: chatID,
+			Error:  &codersdk.ChatStreamError{Message: "failed to load initial snapshot"},
+		})
+	} else {
+		for _, msg := range messages {
+			sdkMsg := db2sdk.ChatMessage(msg)
+			initialSnapshot = append(initialSnapshot, codersdk.ChatStreamEvent{
+				Type:    codersdk.ChatStreamEventTypeMessage,
+				ChatID:  chatID,
+				Message: &sdkMsg,
+			})
+		}
+	}
+
+	// Load initial queue.
+	queued, err := p.db.GetChatQueuedMessages(ctx, chatID)
+	if err != nil {
+		p.logger.Error(ctx, "failed to load initial queued messages",
+			slog.Error(err),
+			slog.F("chat_id", chatID),
+		)
+		initialSnapshot = append(initialSnapshot, codersdk.ChatStreamEvent{
+			Type:   codersdk.ChatStreamEventTypeError,
+			ChatID: chatID,
+			Error:  &codersdk.ChatStreamError{Message: "failed to load initial snapshot"},
+		})
+	} else if len(queued) > 0 {
+		initialSnapshot = append(initialSnapshot, codersdk.ChatStreamEvent{
+			Type:           codersdk.ChatStreamEventTypeQueueUpdate,
+			ChatID:         chatID,
+			QueuedMessages: db2sdk.ChatQueuedMessages(queued),
+		})
+	}
+
+	// Get initial chat state to determine if we need a relay.
+	chat, chatErr := p.db.GetChatByID(ctx, chatID)
+
+	// Include the current chat status in the snapshot so the
+	// frontend can gate message_part processing correctly from
+	// the very first batch, without waiting for a separate REST
+	// query.
+	if chatErr != nil {
+		p.logger.Error(ctx, "failed to load initial chat state",
+			slog.Error(chatErr),
+			slog.F("chat_id", chatID),
+		)
+		initialSnapshot = append(initialSnapshot, codersdk.ChatStreamEvent{
+			Type:   codersdk.ChatStreamEventTypeError,
+			ChatID: chatID,
+			Error:  &codersdk.ChatStreamError{Message: "failed to load initial snapshot"},
+		})
+	} else {
+		statusEvent := codersdk.ChatStreamEvent{
+			Type:   codersdk.ChatStreamEventTypeStatus,
+			ChatID: chatID,
+			Status: &codersdk.ChatStreamStatus{
+				Status: codersdk.ChatStatus(chat.Status),
+			},
+		}
+		// Prepend so the frontend sees the status before any
+		// message_part events.
+		initialSnapshot = append([]codersdk.ChatStreamEvent{statusEvent}, initialSnapshot...)
+	}
+
+	// Track the last message ID we've seen for DB queries.
+	// Initialize from afterMessageID so that when the caller passes
+	// afterMessageID > 0 but no new messages exist yet, the first
+	// pubsub catch-up doesn't re-fetch already-seen messages.
+	lastMessageID := afterMessageID
+	if len(messages) > 0 {
+		lastMessageID = messages[len(messages)-1].ID
+	}
+
 	// When an enterprise SubscribeFn is provided and the chat
 	// lookup succeeded, call it to get relay events (message_parts
 	// from remote replicas). OSS now owns pubsub subscription,
 	// message catch-up, queue updates, and status forwarding;
 	// enterprise only manages relay dialing.
 	var relayEvents <-chan codersdk.ChatStreamEvent
-	var relayCleanup func()
 	var statusNotifications chan StatusNotification
-	if p.subscribeFn != nil && err == nil {
+	if p.subscribeFn != nil && chatErr == nil {
 		statusNotifications = make(chan StatusNotification, 10)
-		var relayEvCh <-chan codersdk.ChatStreamEvent
-		relayEvCh, relayCleanup = p.subscribeFn(mergedCtx, SubscribeFnParams{
+		relayEvents = p.subscribeFn(mergedCtx, SubscribeFnParams{
 			ChatID:              chatID,
 			Chat:                chat,
 			WorkerID:            p.workerID,
@@ -1195,9 +1294,7 @@ func (p *Server) Subscribe(
 			DB:                  p.db,
 			Logger:              p.logger,
 		})
-		relayEvents = relayEvCh
 	}
-
 	hasPubsub := false
 	if p.pubsub != nil {
 		// hasPubsub is only true when we actually subscribed
@@ -1367,9 +1464,6 @@ func (p *Server) Subscribe(
 				cancelFn()
 			}
 		}
-		if relayCleanup != nil {
-			relayCleanup()
-		}
 	}
 	return initialSnapshot, mergedEvents, cancel, true
 }
@@ -1538,6 +1632,20 @@ func (p *Server) publishMessage(chatID uuid.UUID, message database.ChatMessage)
 	})
 }
 
+// publishEditedMessage is like publishMessage but uses
+// AfterMessageID=0 so remote subscribers re-fetch from the
+// beginning, ensuring the edit is never silently dropped.
+func (p *Server) publishEditedMessage(chatID uuid.UUID, message database.ChatMessage) {
+	sdkMessage := db2sdk.ChatMessage(message)
+	p.publishEvent(chatID, codersdk.ChatStreamEvent{
+		Type:    codersdk.ChatStreamEventTypeMessage,
+		Message: &sdkMessage,
+	})
+	p.publishChatStreamNotify(chatID, coderdpubsub.ChatStreamNotifyMessage{
+		AfterMessageID: 0,
+	})
+}
+
 func (p *Server) publishMessagePart(chatID uuid.UUID, role string, part codersdk.ChatMessagePart) {
 	if part.Type == "" {
 		return
@@ -1704,6 +1812,7 @@ func (p *Server) processChat(ctx context.Context, chat database.Chat) {
 	lastError := ""
 	remainingQueuedMessages := []database.ChatQueuedMessage{}
 	shouldPublishQueueUpdate := false
+	var promotedMessage *database.ChatMessage
 
 	defer func() {
 		// Use a context that is not canceled by Close() so we can
@@ -1744,7 +1853,7 @@ func (p *Server) processChat(ctx context.Context, chat database.Chat) {
 			// If someone else already set the chat to pending (e.g.
 			// the promote endpoint), don't overwrite it — just clear
 			// the worker and let the processor pick it back up.
-			if latestChat.Status == database.ChatStatusPending && status == database.ChatStatusWaiting {
+			if latestChat.Status == database.ChatStatusPending {
 				status = database.ChatStatusPending
 			} else if status == database.ChatStatusWaiting {
 				// Try to auto-promote the next queued message.
@@ -1773,8 +1882,7 @@ func (p *Server) processChat(ctx context.Context, chat database.Chat) {
 							slog.F("queued_message_id", nextQueued.ID), slog.Error(insertErr))
 					} else {
 						status = database.ChatStatusPending
-
-						p.publishMessage(chat.ID, msg)
+						promotedMessage = &msg
 
 						remaining, qErr := tx.GetChatQueuedMessages(cleanupCtx, chat.ID)
 						if qErr == nil {
@@ -1803,8 +1911,13 @@ func (p *Server) processChat(ctx context.Context, chat database.Chat) {
 		}
 		if err != nil {
 			logger.Error(cleanupCtx, "failed to release chat", slog.Error(err))
+			return
 		}
-		if err == nil && shouldPublishQueueUpdate {
+
+		if promotedMessage != nil {
+			p.publishMessage(chat.ID, *promotedMessage)
+		}
+		if shouldPublishQueueUpdate {
 			p.publishEvent(chat.ID, codersdk.ChatStreamEvent{
 				Type:           codersdk.ChatStreamEventTypeQueueUpdate,
 				QueuedMessages: db2sdk.ChatQueuedMessages(remainingQueuedMessages),
@@ -1840,7 +1953,6 @@ func (p *Server) processChat(ctx context.Context, chat database.Chat) {
 					Body:  "Agent has finished running.",
 					Icon:  "/favicon.ico",
 					Data:  map[string]string{"url": fmt.Sprintf("/agents/%s", chat.ID)},
-					Tag:   chat.ID.String(),
 				}
 				if status == database.ChatStatusError {
 					pushMsg.Body = "Agent encountered an error."
@@ -2033,10 +2145,7 @@ func (p *Server) runChat(
 		if conn == nil {
 			conn = agentConn
 			releaseConn = agentRelease
-			chatStateMu.Unlock()
 
-			// Inject chat identity headers so agent-side
-			// handlers can track which paths this chat edits.
 			var ancestorIDs []string
 			if chatSnapshot.ParentChatID.Valid {
 				ancestorIDs = append(ancestorIDs, chatSnapshot.ParentChatID.UUID.String())
@@ -2051,6 +2160,7 @@ func (p *Server) runChat(
 				workspacesdk.CoderAncestorChatIDsHeader: {string(ancestorJSON)},
 			})
 
+			chatStateMu.Unlock()
 			return agentConn, nil
 		}
 		currentConn := conn
@@ -2070,6 +2180,16 @@ func (p *Server) runChat(
 	modelConfigContextLimit := modelConfig.ContextLimit
 
 	persistStep := func(persistCtx context.Context, step chatloop.PersistedStep) error {
+		// If the chat context has been canceled (e.g. by an
+		// EditMessage call), bail out before inserting any
+		// messages. This closes the race window between
+		// EditMessage committing its transaction (which deletes
+		// messages after the edit point) and the cancellation
+		// propagating to the processing loop.
+		if persistCtx.Err() != nil {
+			return chatloop.ErrInterrupted
+		}
+
 		// Split the step content into assistant blocks and tool
 		// result blocks so they can be stored as separate messages
 		// with the appropriate roles.
@@ -2087,66 +2207,77 @@ func (p *Server) runChat(
 			assistantBlocks = append(assistantBlocks, block)
 		}
 
-		if len(assistantBlocks) > 0 {
-			assistantContent, err := chatprompt.MarshalContent(assistantBlocks, nil)
-			if err != nil {
-				return err
+		var insertedMessages []database.ChatMessage
+		err := p.db.InTx(func(tx database.Store) error {
+			if len(assistantBlocks) > 0 {
+				assistantContent, marshalErr := chatprompt.MarshalContent(assistantBlocks, nil)
+				if marshalErr != nil {
+					return marshalErr
+				}
+
+				hasUsage := step.Usage != (fantasy.Usage{})
+				assistantMessage, insertErr := tx.InsertChatMessage(persistCtx, database.InsertChatMessageParams{
+					ChatID:        chat.ID,
+					ModelConfigID: uuid.NullUUID{UUID: modelConfig.ID, Valid: true},
+					Role:          string(fantasy.MessageRoleAssistant),
+					Content:       assistantContent,
+					Visibility:    database.ChatMessageVisibilityBoth,
+					InputTokens:   usageNullInt64(step.Usage.InputTokens, hasUsage),
+					OutputTokens:  usageNullInt64(step.Usage.OutputTokens, hasUsage),
+					TotalTokens:   usageNullInt64(step.Usage.TotalTokens, hasUsage),
+					ReasoningTokens: usageNullInt64(
+						step.Usage.ReasoningTokens,
+						hasUsage,
+					),
+					CacheCreationTokens: usageNullInt64(
+						step.Usage.CacheCreationTokens,
+						hasUsage,
+					),
+					CacheReadTokens: usageNullInt64(step.Usage.CacheReadTokens, hasUsage),
+					ContextLimit:    step.ContextLimit,
+					Compressed:      sql.NullBool{},
+				})
+				if insertErr != nil {
+					return xerrors.Errorf("insert assistant message: %w", insertErr)
+				}
+				insertedMessages = append(insertedMessages, assistantMessage)
 			}
 
-			hasUsage := step.Usage != (fantasy.Usage{})
-			assistantMessage, err := p.db.InsertChatMessage(persistCtx, database.InsertChatMessageParams{
-				ChatID:        chat.ID,
-				ModelConfigID: uuid.NullUUID{UUID: modelConfig.ID, Valid: true},
-				Role:          string(fantasy.MessageRoleAssistant),
-				Content:       assistantContent,
-				Visibility:    database.ChatMessageVisibilityBoth,
-				InputTokens:   usageNullInt64(step.Usage.InputTokens, hasUsage),
-				OutputTokens:  usageNullInt64(step.Usage.OutputTokens, hasUsage),
-				TotalTokens:   usageNullInt64(step.Usage.TotalTokens, hasUsage),
-				ReasoningTokens: usageNullInt64(
-					step.Usage.ReasoningTokens,
-					hasUsage,
-				),
-				CacheCreationTokens: usageNullInt64(
-					step.Usage.CacheCreationTokens,
-					hasUsage,
-				),
-				CacheReadTokens: usageNullInt64(step.Usage.CacheReadTokens, hasUsage),
-				ContextLimit:    step.ContextLimit,
-				Compressed:      sql.NullBool{},
-			})
-			if err != nil {
-				return xerrors.Errorf("insert assistant message: %w", err)
+			for _, tr := range toolResults {
+				resultContent, marshalErr := chatprompt.MarshalToolResultContent(tr)
+				if marshalErr != nil {
+					return marshalErr
+				}
+
+				toolMessage, insertErr := tx.InsertChatMessage(persistCtx, database.InsertChatMessageParams{
+					ChatID:              chat.ID,
+					ModelConfigID:       uuid.NullUUID{UUID: modelConfig.ID, Valid: true},
+					Role:                string(fantasy.MessageRoleTool),
+					Content:             resultContent,
+					Visibility:          database.ChatMessageVisibilityBoth,
+					InputTokens:         sql.NullInt64{},
+					OutputTokens:        sql.NullInt64{},
+					TotalTokens:         sql.NullInt64{},
+					ReasoningTokens:     sql.NullInt64{},
+					CacheCreationTokens: sql.NullInt64{},
+					CacheReadTokens:     sql.NullInt64{},
+					ContextLimit:        sql.NullInt64{},
+					Compressed:          sql.NullBool{},
+				})
+				if insertErr != nil {
+					return xerrors.Errorf("insert tool result: %w", insertErr)
+				}
+				insertedMessages = append(insertedMessages, toolMessage)
 			}
-			p.publishMessage(chat.ID, assistantMessage)
+
+			return nil
+		}, nil)
+		if err != nil {
+			return xerrors.Errorf("persist step transaction: %w", err)
 		}
 
-		for _, tr := range toolResults {
-			resultContent, err := chatprompt.MarshalToolResultContent(tr)
-			if err != nil {
-				return err
-			}
-
-			toolMessage, err := p.db.InsertChatMessage(persistCtx, database.InsertChatMessageParams{
-				ChatID:              chat.ID,
-				ModelConfigID:       uuid.NullUUID{UUID: modelConfig.ID, Valid: true},
-				Role:                string(fantasy.MessageRoleTool),
-				Content:             resultContent,
-				Visibility:          database.ChatMessageVisibilityBoth,
-				InputTokens:         sql.NullInt64{},
-				OutputTokens:        sql.NullInt64{},
-				TotalTokens:         sql.NullInt64{},
-				ReasoningTokens:     sql.NullInt64{},
-				CacheCreationTokens: sql.NullInt64{},
-				CacheReadTokens:     sql.NullInt64{},
-				ContextLimit:        sql.NullInt64{},
-				Compressed:          sql.NullBool{},
-			})
-			if err != nil {
-				return xerrors.Errorf("insert tool result: %w", err)
-			}
-
-			p.publishMessage(chat.ID, toolMessage)
+		for _, msg := range insertedMessages {
+			p.publishMessage(chat.ID, msg)
 		}
 
 		// Clear the stream buffer now that the step is
@@ -2160,7 +2291,6 @@ func (p *Server) runChat(
 
 		return nil
 	}
-
 	// Apply the default MaxOutputTokens if the model config
 	// does not specify one.
 	if callConfig.MaxOutputTokens == nil {
@@ -2308,6 +2438,12 @@ func (p *Server) runChat(
 		},
 
 		OnRetry: func(attempt int, retryErr error, delay time.Duration) {
+			p.streamMu.Lock()
+			if state, ok := p.chatStreams[chat.ID]; ok {
+				state.buffer = nil
+			}
+			p.streamMu.Unlock()
+
 			logger.Warn(ctx, "retrying LLM stream",
 				slog.F("attempt", attempt),
 				slog.F("delay", delay.String()),
@@ -2351,28 +2487,6 @@ func (p *Server) persistChatContextSummary(
 		return xerrors.Errorf("encode system summary: %w", err)
 	}
 
-	_, err = p.db.InsertChatMessage(ctx, database.InsertChatMessageParams{
-		ChatID:        chatID,
-		ModelConfigID: uuid.NullUUID{UUID: modelConfigID, Valid: true},
-		Role:          string(fantasy.MessageRoleSystem),
-		Content: pqtype.NullRawMessage{
-			RawMessage: systemContent,
-			Valid:      len(systemContent) > 0,
-		},
-		Visibility:          database.ChatMessageVisibilityModel,
-		Compressed:          sql.NullBool{Bool: true, Valid: true},
-		InputTokens:         sql.NullInt64{},
-		OutputTokens:        sql.NullInt64{},
-		TotalTokens:         sql.NullInt64{},
-		ReasoningTokens:     sql.NullInt64{},
-		CacheCreationTokens: sql.NullInt64{},
-		CacheReadTokens:     sql.NullInt64{},
-		ContextLimit:        sql.NullInt64{},
-	})
-	if err != nil {
-		return xerrors.Errorf("insert hidden summary message: %w", err)
-	}
-
 	args, err := json.Marshal(map[string]any{
 		"source":            "automatic",
 		"threshold_percent": result.ThresholdPercent,
@@ -2392,29 +2506,7 @@ func (p *Server) persistChatContextSummary(
 		return xerrors.Errorf("encode summary tool call: %w", err)
 	}
 
-	assistantMessage, err := p.db.InsertChatMessage(ctx, database.InsertChatMessageParams{
-		ChatID:        chatID,
-		ModelConfigID: uuid.NullUUID{UUID: modelConfigID, Valid: true},
-		Role:          string(fantasy.MessageRoleAssistant),
-		Content:       assistantContent,
-		Visibility:    database.ChatMessageVisibilityUser,
-		Compressed: sql.NullBool{
-			Bool:  true,
-			Valid: true,
-		},
-		InputTokens:         sql.NullInt64{},
-		OutputTokens:        sql.NullInt64{},
-		TotalTokens:         sql.NullInt64{},
-		ReasoningTokens:     sql.NullInt64{},
-		CacheCreationTokens: sql.NullInt64{},
-		CacheReadTokens:     sql.NullInt64{},
-		ContextLimit:        sql.NullInt64{},
-	})
-	if err != nil {
-		return xerrors.Errorf("insert summary tool call message: %w", err)
-	}
-
-	summaryResult, marshalErr := json.Marshal(map[string]any{
+	summaryResult, err := json.Marshal(map[string]any{
 		"summary":              result.SummaryReport,
 		"source":               "automatic",
 		"threshold_percent":    result.ThresholdPercent,
@@ -2422,8 +2514,8 @@ func (p *Server) persistChatContextSummary(
 		"context_tokens":       result.ContextTokens,
 		"context_limit_tokens": result.ContextLimit,
 	})
-	if marshalErr != nil {
-		return xerrors.Errorf("encode summary result payload: %w", marshalErr)
+	if err != nil {
+		return xerrors.Errorf("encode summary result payload: %w", err)
 	}
 	toolResult, err := chatprompt.MarshalToolResult(
 		toolCallID,
@@ -2435,30 +2527,88 @@ func (p *Server) persistChatContextSummary(
 		return xerrors.Errorf("encode summary tool result: %w", err)
 	}
 
-	toolMessage, err := p.db.InsertChatMessage(ctx, database.InsertChatMessageParams{
-		ChatID:        chatID,
-		ModelConfigID: uuid.NullUUID{UUID: modelConfigID, Valid: true},
-		Role:          string(fantasy.MessageRoleTool),
-		Content:       toolResult,
-		Visibility:    database.ChatMessageVisibilityBoth,
-		Compressed: sql.NullBool{
-			Bool:  true,
-			Valid: true,
-		},
-		InputTokens:         sql.NullInt64{},
-		OutputTokens:        sql.NullInt64{},
-		TotalTokens:         sql.NullInt64{},
-		ReasoningTokens:     sql.NullInt64{},
-		CacheCreationTokens: sql.NullInt64{},
-		CacheReadTokens:     sql.NullInt64{},
-		ContextLimit:        sql.NullInt64{},
-	})
-	if err != nil {
-		return xerrors.Errorf("insert summary tool result message: %w", err)
+	var insertedMessages []database.ChatMessage
+
+	txErr := p.db.InTx(func(tx database.Store) error {
+		_, txErr := tx.InsertChatMessage(ctx, database.InsertChatMessageParams{
+			ChatID:        chatID,
+			ModelConfigID: uuid.NullUUID{UUID: modelConfigID, Valid: true},
+			Role:          string(fantasy.MessageRoleSystem),
+			Content: pqtype.NullRawMessage{
+				RawMessage: systemContent,
+				Valid:      len(systemContent) > 0,
+			},
+			Visibility:          database.ChatMessageVisibilityModel,
+			Compressed:          sql.NullBool{Bool: true, Valid: true},
+			InputTokens:         sql.NullInt64{},
+			OutputTokens:        sql.NullInt64{},
+			TotalTokens:         sql.NullInt64{},
+			ReasoningTokens:     sql.NullInt64{},
+			CacheCreationTokens: sql.NullInt64{},
+			CacheReadTokens:     sql.NullInt64{},
+			ContextLimit:        sql.NullInt64{},
+		})
+		if txErr != nil {
+			return xerrors.Errorf("insert hidden summary message: %w", txErr)
+		}
+
+		assistantMessage, txErr := tx.InsertChatMessage(ctx, database.InsertChatMessageParams{
+			ChatID:        chatID,
+			ModelConfigID: uuid.NullUUID{UUID: modelConfigID, Valid: true},
+			Role:          string(fantasy.MessageRoleAssistant),
+			Content:       assistantContent,
+			Visibility:    database.ChatMessageVisibilityUser,
+			Compressed: sql.NullBool{
+				Bool:  true,
+				Valid: true,
+			},
+			InputTokens:         sql.NullInt64{},
+			OutputTokens:        sql.NullInt64{},
+			TotalTokens:         sql.NullInt64{},
+			ReasoningTokens:     sql.NullInt64{},
+			CacheCreationTokens: sql.NullInt64{},
+			CacheReadTokens:     sql.NullInt64{},
+			ContextLimit:        sql.NullInt64{},
+		})
+		if txErr != nil {
+			return xerrors.Errorf("insert summary tool call message: %w", txErr)
+		}
+		insertedMessages = append(insertedMessages, assistantMessage)
+
+		toolMessage, txErr := tx.InsertChatMessage(ctx, database.InsertChatMessageParams{
+			ChatID:        chatID,
+			ModelConfigID: uuid.NullUUID{UUID: modelConfigID, Valid: true},
+			Role:          string(fantasy.MessageRoleTool),
+			Content:       toolResult,
+			Visibility:    database.ChatMessageVisibilityBoth,
+			Compressed: sql.NullBool{
+				Bool:  true,
+				Valid: true,
+			},
+			InputTokens:         sql.NullInt64{},
+			OutputTokens:        sql.NullInt64{},
+			TotalTokens:         sql.NullInt64{},
+			ReasoningTokens:     sql.NullInt64{},
+			CacheCreationTokens: sql.NullInt64{},
+			CacheReadTokens:     sql.NullInt64{},
+			ContextLimit:        sql.NullInt64{},
+		})
+		if txErr != nil {
+			return xerrors.Errorf("insert summary tool result message: %w", txErr)
+		}
+		insertedMessages = append(insertedMessages, toolMessage)
+
+		return nil
+	}, nil)
+	if txErr != nil {
+		return txErr
 	}
 
-	p.publishMessage(chatID, assistantMessage)
-	p.publishMessage(chatID, toolMessage)
+	// Publish after transaction commits to avoid notifying
+	// subscribers about messages that could be rolled back.
+	for _, msg := range insertedMessages {
+		p.publishMessage(chatID, msg)
+	}
 	return nil
 }
 
@@ -2666,26 +2816,63 @@ func (p *Server) recoverStaleChats(ctx context.Context) {
 		return
 	}
 
+	recovered := 0
 	for _, chat := range staleChats {
 		p.logger.Info(ctx, "recovering stale chat", slog.F("chat_id", chat.ID))
 
-		// Reset to pending so any replica can pick it up.
-		_, err := p.db.UpdateChatStatus(ctx, database.UpdateChatStatusParams{
-			ID:          chat.ID,
-			Status:      database.ChatStatusPending,
-			WorkerID:    uuid.NullUUID{},
-			StartedAt:   sql.NullTime{},
-			HeartbeatAt: sql.NullTime{},
-			LastError:   sql.NullString{},
-		})
+		// Use a transaction with FOR UPDATE to avoid a TOCTOU race:
+		// between GetStaleChats (a bare SELECT) and here, the chat's
+		// heartbeat may have been refreshed. We re-check freshness
+		// under the row lock before resetting.
+		err := p.db.InTx(func(tx database.Store) error {
+			locked, lockErr := tx.GetChatByIDForUpdate(ctx, chat.ID)
+			if lockErr != nil {
+				return xerrors.Errorf("lock chat for recovery: %w", lockErr)
+			}
+
+			// Only recover chats that are still running.
+			// Between GetStaleChats and this lock, the chat
+			// may have completed normally.
+			if locked.Status != database.ChatStatusRunning {
+				p.logger.Debug(ctx, "chat status changed since snapshot, skipping recovery",
+					slog.F("chat_id", chat.ID),
+					slog.F("status", locked.Status))
+				return nil
+			}
+
+			// Re-check: only recover if the chat is still stale.
+			// A valid heartbeat that is at or after the stale
+			// threshold means the chat was refreshed after our
+			// initial snapshot — skip it.
+			if locked.HeartbeatAt.Valid && !locked.HeartbeatAt.Time.Before(staleAfter) {
+				p.logger.Debug(ctx, "chat heartbeat refreshed since snapshot, skipping recovery",
+					slog.F("chat_id", chat.ID))
+				return nil
+			}
+
+			// Reset to pending so any replica can pick it up.
+			_, updateErr := tx.UpdateChatStatus(ctx, database.UpdateChatStatusParams{
+				ID:          chat.ID,
+				Status:      database.ChatStatusPending,
+				WorkerID:    uuid.NullUUID{},
+				StartedAt:   sql.NullTime{},
+				HeartbeatAt: sql.NullTime{},
+				LastError:   sql.NullString{},
+			})
+			if updateErr != nil {
+				return updateErr
+			}
+			recovered++
+			return nil
+		}, nil)
 		if err != nil {
 			p.logger.Error(ctx, "failed to recover stale chat",
 				slog.F("chat_id", chat.ID), slog.Error(err))
 		}
 	}
 
-	if len(staleChats) > 0 {
-		p.logger.Info(ctx, "recovered stale chats", slog.F("count", len(staleChats)))
+	if recovered > 0 {
+		p.logger.Info(ctx, "recovered stale chats", slog.F("count", recovered))
 	}
 }
 

coderd/chatd/chatd_test.go

@@ -6,7 +6,6 @@ import (
 	"encoding/json"
 	"errors"
 	"fmt"
-	"net/http"
 	"strings"
 	"sync"
 	"sync/atomic"
@@ -17,8 +16,6 @@ import (
 	"github.com/google/uuid"
 	"github.com/sqlc-dev/pqtype"
 	"github.com/stretchr/testify/require"
-	"go.uber.org/mock/gomock"
-	"golang.org/x/xerrors"
 
 	"cdr.dev/slog/v3/sloggers/slogtest"
 	"github.com/coder/coder/v2/agent/agenttest"
@@ -32,8 +29,6 @@ import (
 	dbpubsub "github.com/coder/coder/v2/coderd/database/pubsub"
 	"github.com/coder/coder/v2/coderd/util/slice"
 	"github.com/coder/coder/v2/codersdk"
-	"github.com/coder/coder/v2/codersdk/workspacesdk"
-	"github.com/coder/coder/v2/codersdk/workspacesdk/agentconnmock"
 	"github.com/coder/coder/v2/provisioner/echo"
 	proto "github.com/coder/coder/v2/provisionersdk/proto"
 	"github.com/coder/coder/v2/testutil"
@@ -78,10 +73,11 @@ func TestInterruptChatBroadcastsStatusAcrossInstances(t *testing.T) {
 	require.Eventually(t, func() bool {
 		select {
 		case event := <-events:
-			if event.Type != codersdk.ChatStreamEventTypeStatus || event.Status == nil {
-				return false
+			if event.Type == codersdk.ChatStreamEventTypeStatus && event.Status != nil {
+				return event.Status.Status == codersdk.ChatStatusWaiting
 			}
-			return event.Status.Status == codersdk.ChatStatusWaiting
+			t.Logf("skipping unexpected event: type=%s", event.Type)
+			return false
 		default:
 			return false
 		}
@@ -870,15 +866,15 @@ func TestSubscribeNoPubsubNoDuplicateMessageParts(t *testing.T) {
 	// events — the snapshot already contained everything. Before
 	// the fix, localSnapshot was replayed into the channel,
 	// causing duplicates.
-	select {
-	case event, ok := <-events:
-		if ok {
-			t.Fatalf("unexpected event from channel (would be a duplicate): type=%s", event.Type)
+	require.Never(t, func() bool {
+		select {
+		case <-events:
+			return true
+		default:
+			return false
 		}
-		// Channel closed without events is fine.
-	case <-time.After(200 * time.Millisecond):
-		// No events — correct behavior.
-	}
+	}, 200*time.Millisecond, testutil.IntervalFast,
+		"expected no duplicate events after snapshot")
 }
 
 func TestSubscribeAfterMessageID(t *testing.T) {
@@ -1533,13 +1529,16 @@ func TestSuccessfulChatSendsWebPushWithNavigationData(t *testing.T) {
 	})
 	require.NoError(t, err)
 
-	// Wait for a web push notification to be dispatched. The dispatch
-	// happens asynchronously after the DB status is updated, so we need
-	// to poll rather than assert immediately.
-	testutil.Eventually(ctx, t, func(_ context.Context) bool {
-		return mockPush.dispatchCount.Load() >= 1
+	// Wait for the chat to complete and return to waiting status.
+	testutil.Eventually(ctx, t, func(ctx context.Context) bool {
+		fromDB, dbErr := db.GetChatByID(ctx, chat.ID)
+		if dbErr != nil {
+			return false
+		}
+		return fromDB.Status == database.ChatStatusWaiting && !fromDB.WorkerID.Valid && mockPush.dispatchCount.Load() == 1
 	}, testutil.IntervalFast)
 
+	// Verify a web push notification was dispatched exactly once.
 	require.Equal(t, int32(1), mockPush.dispatchCount.Load(),
 		"expected exactly one web push dispatch for a completed chat")
 
@@ -1558,75 +1557,6 @@ func TestSuccessfulChatSendsWebPushWithNavigationData(t *testing.T) {
 		"web push Data should contain the chat navigation URL")
 }
 
-func TestSuccessfulChatSendsWebPushWithTag(t *testing.T) {
-	t.Parallel()
-
-	db, ps := dbtestutil.NewDB(t)
-	ctx := testutil.Context(t, testutil.WaitLong)
-
-	// Set up a mock OpenAI that returns a simple streaming response.
-	openAIURL := chattest.NewOpenAI(t, func(req *chattest.OpenAIRequest) chattest.OpenAIResponse {
-		if !req.Stream {
-			return chattest.OpenAINonStreamingResponse("title")
-		}
-		return chattest.OpenAIStreamingResponse(chattest.OpenAITextChunks("done")...)
-	})
-
-	// Mock webpush dispatcher that captures calls.
-	mockPush := &mockWebpushDispatcher{}
-
-	logger := slogtest.Make(t, &slogtest.Options{IgnoreErrors: true})
-	server := chatd.New(chatd.Config{
-		Logger:                     logger,
-		Database:                   db,
-		ReplicaID:                  uuid.New(),
-		Pubsub:                     ps,
-		PendingChatAcquireInterval: 10 * time.Millisecond,
-		InFlightChatStaleAfter:     testutil.WaitSuperLong,
-		WebpushDispatcher:          mockPush,
-	})
-	t.Cleanup(func() {
-		require.NoError(t, server.Close())
-	})
-
-	user, model := seedChatDependencies(ctx, t, db)
-	setOpenAIProviderBaseURL(ctx, t, db, openAIURL)
-
-	chat, err := server.CreateChat(ctx, chatd.CreateOptions{
-		OwnerID:            user.ID,
-		Title:              "push-tag-test",
-		ModelConfigID:      model.ID,
-		InitialUserContent: []fantasy.Content{fantasy.TextContent{Text: "hello"}},
-	})
-	require.NoError(t, err)
-
-	// Wait for the web push notification to be dispatched.
-	// We poll dispatchCount rather than DB status because the
-	// push fires after the status update, creating a small race
-	// window.
-	testutil.Eventually(ctx, t, func(_ context.Context) bool {
-		return mockPush.dispatchCount.Load() >= 1
-	}, testutil.IntervalFast)
-
-	require.Equal(t, int32(1), mockPush.dispatchCount.Load(),
-		"expected exactly one web push dispatch for a completed chat")
-
-	// Verify the push notification tag is set to the chat ID for dedup.
-	mockPush.mu.Lock()
-	capturedMsg := mockPush.lastMessage
-	capturedUser := mockPush.lastUserID
-	mockPush.mu.Unlock()
-
-	require.Equal(t, chat.ID.String(), capturedMsg.Tag,
-		"push notification tag should equal the chat ID for deduplication")
-	require.Equal(t, user.ID, capturedUser,
-		"push notification should be dispatched to the chat owner")
-	require.Equal(t, "push-tag-test", capturedMsg.Title,
-		"push notification title should match the chat title")
-	require.Equal(t, "Agent has finished running.", capturedMsg.Body,
-		"push notification body should indicate the agent finished")
-}
-
 func TestCloseDuringShutdownContextCanceledShouldRetryOnNewReplica(t *testing.T) {
 	t.Parallel()
 
@@ -1733,260 +1663,3 @@ func TestCloseDuringShutdownContextCanceledShouldRetryOnNewReplica(t *testing.T)
 			!fromDB.LastError.Valid
 	}, testutil.WaitMedium, testutil.IntervalFast)
 }
-
-func TestHeaderInjection(t *testing.T) {
-	t.Parallel()
-
-	// seedWorkspaceAgent creates the DB entities needed so that
-	// GetWorkspaceAgentsInLatestBuildByWorkspaceID returns an
-	// agent for the given workspace.
-	seedWorkspaceAgent := func(
-		t *testing.T,
-		db database.Store,
-		ps dbpubsub.Pubsub,
-		ownerID uuid.UUID,
-		orgID uuid.UUID,
-	) (workspaceID uuid.UUID, agentID uuid.UUID) {
-		t.Helper()
-
-		// TemplateVersion needs its own provisioner job.
-		versionJob := dbgen.ProvisionerJob(t, db, ps, database.ProvisionerJob{
-			OrganizationID: orgID,
-			InitiatorID:    ownerID,
-			Type:           database.ProvisionerJobTypeTemplateVersionImport,
-		})
-		tv := dbgen.TemplateVersion(t, db, database.TemplateVersion{
-			OrganizationID: orgID,
-			CreatedBy:      ownerID,
-			JobID:          versionJob.ID,
-		})
-		templ := dbgen.Template(t, db, database.Template{
-			OrganizationID:  orgID,
-			CreatedBy:       ownerID,
-			ActiveVersionID: tv.ID,
-		})
-		ws := dbgen.Workspace(t, db, database.WorkspaceTable{
-			OwnerID:        ownerID,
-			OrganizationID: orgID,
-			TemplateID:     templ.ID,
-		})
-		buildJob := dbgen.ProvisionerJob(t, db, ps, database.ProvisionerJob{
-			OrganizationID: orgID,
-			InitiatorID:    ownerID,
-			Type:           database.ProvisionerJobTypeWorkspaceBuild,
-		})
-		build := dbgen.WorkspaceBuild(t, db, database.WorkspaceBuild{
-			WorkspaceID:       ws.ID,
-			JobID:             buildJob.ID,
-			BuildNumber:       1,
-			InitiatorID:       ownerID,
-			TemplateVersionID: tv.ID,
-		})
-		resource := dbgen.WorkspaceResource(t, db, database.WorkspaceResource{
-			JobID: build.JobID,
-		})
-		agent := dbgen.WorkspaceAgent(t, db, database.WorkspaceAgent{
-			ResourceID: resource.ID,
-		})
-		return ws.ID, agent.ID
-	}
-
-	t.Run("WithParentChat", func(t *testing.T) {
-		t.Parallel()
-
-		db, ps := dbtestutil.NewDB(t)
-		ctx := testutil.Context(t, testutil.WaitLong)
-		user, model := seedChatDependencies(ctx, t, db)
-
-		org, err := db.GetDefaultOrganization(ctx)
-		require.NoError(t, err)
-
-		workspaceID, expectedAgentID := seedWorkspaceAgent(t, db, ps, user.ID, org.ID)
-
-		// Set up the mock OpenAI to return a simple text response
-		// so the chat finishes cleanly.
-		openAIURL := chattest.NewOpenAI(t, func(req *chattest.OpenAIRequest) chattest.OpenAIResponse {
-			if !req.Stream {
-				return chattest.OpenAINonStreamingResponse("title")
-			}
-			return chattest.OpenAIStreamingResponse(
-				chattest.OpenAITextChunks("done")...,
-			)
-		})
-		setOpenAIProviderBaseURL(ctx, t, db, openAIURL)
-
-		// Wire up the mock agent connection so we can capture
-		// the headers passed to SetExtraHeaders.
-		ctrl := gomock.NewController(t)
-		mockConn := agentconnmock.NewMockAgentConn(ctrl)
-
-		var capturedHeaders http.Header
-		headersCaptured := make(chan struct{})
-
-		// SetExtraHeaders is called once when the connection
-		// is first established.
-		mockConn.EXPECT().SetExtraHeaders(gomock.Any()).Do(func(h http.Header) {
-			capturedHeaders = h
-			close(headersCaptured)
-		})
-		// resolveInstructions calls LS to look for instruction
-		// files; return an error so it skips gracefully.
-		mockConn.EXPECT().LS(gomock.Any(), gomock.Any(), gomock.Any()).Return(
-			workspacesdk.LSResponse{}, xerrors.New("not found"),
-		).AnyTimes()
-		// The connection is closed when the chat finishes.
-		mockConn.EXPECT().Close().Return(nil).AnyTimes()
-
-		agentConnFn := func(_ context.Context, agentID uuid.UUID) (workspacesdk.AgentConn, func(), error) {
-			require.Equal(t, expectedAgentID, agentID)
-			return mockConn, func() {}, nil
-		}
-
-		logger := slogtest.Make(t, &slogtest.Options{IgnoreErrors: true})
-		server := chatd.New(chatd.Config{
-			Logger:                     logger,
-			Database:                   db,
-			ReplicaID:                  uuid.New(),
-			Pubsub:                     ps,
-			AgentConn:                  agentConnFn,
-			PendingChatAcquireInterval: 10 * time.Millisecond,
-			InFlightChatStaleAfter:     testutil.WaitSuperLong,
-		})
-		t.Cleanup(func() {
-			require.NoError(t, server.Close())
-		})
-
-		// Create a real parent chat so the FK constraint is
-		// satisfied.
-		parentChat, err := server.CreateChat(ctx, chatd.CreateOptions{
-			OwnerID:       user.ID,
-			Title:         "parent-chat",
-			ModelConfigID: model.ID,
-			InitialUserContent: []fantasy.Content{
-				fantasy.TextContent{Text: "parent"},
-			},
-		})
-		require.NoError(t, err)
-
-		chat, err := server.CreateChat(ctx, chatd.CreateOptions{
-			OwnerID:       user.ID,
-			WorkspaceID:   uuid.NullUUID{UUID: workspaceID, Valid: true},
-			ParentChatID:  uuid.NullUUID{UUID: parentChat.ID, Valid: true},
-			Title:         "header-injection-parent",
-			ModelConfigID: model.ID,
-			InitialUserContent: []fantasy.Content{
-				fantasy.TextContent{Text: "hello"},
-			},
-		})
-		require.NoError(t, err)
-
-		// Wait for the chat to be processed and headers to be
-		// captured.
-		select {
-		case <-headersCaptured:
-		case <-ctx.Done():
-			require.FailNow(t, "timed out waiting for SetExtraHeaders")
-		}
-
-		require.Equal(t,
-			chat.ID.String(),
-			capturedHeaders.Get(workspacesdk.CoderChatIDHeader),
-		)
-
-		ancestorJSON := capturedHeaders.Get(workspacesdk.CoderAncestorChatIDsHeader)
-		var ancestorIDs []string
-		err = json.Unmarshal([]byte(ancestorJSON), &ancestorIDs)
-		require.NoError(t, err)
-		require.Equal(t, []string{parentChat.ID.String()}, ancestorIDs)
-	})
-
-	t.Run("WithoutParentChat", func(t *testing.T) {
-		t.Parallel()
-
-		db, ps := dbtestutil.NewDB(t)
-		ctx := testutil.Context(t, testutil.WaitLong)
-		user, model := seedChatDependencies(ctx, t, db)
-
-		org, err := db.GetDefaultOrganization(ctx)
-		require.NoError(t, err)
-
-		workspaceID, expectedAgentID := seedWorkspaceAgent(t, db, ps, user.ID, org.ID)
-
-		openAIURL := chattest.NewOpenAI(t, func(req *chattest.OpenAIRequest) chattest.OpenAIResponse {
-			if !req.Stream {
-				return chattest.OpenAINonStreamingResponse("title")
-			}
-			return chattest.OpenAIStreamingResponse(
-				chattest.OpenAITextChunks("done")...,
-			)
-		})
-		setOpenAIProviderBaseURL(ctx, t, db, openAIURL)
-
-		ctrl := gomock.NewController(t)
-		mockConn := agentconnmock.NewMockAgentConn(ctrl)
-
-		var capturedHeaders http.Header
-		headersCaptured := make(chan struct{})
-
-		mockConn.EXPECT().SetExtraHeaders(gomock.Any()).Do(func(h http.Header) {
-			capturedHeaders = h
-			close(headersCaptured)
-		})
-		mockConn.EXPECT().LS(gomock.Any(), gomock.Any(), gomock.Any()).Return(
-			workspacesdk.LSResponse{}, xerrors.New("not found"),
-		).AnyTimes()
-		mockConn.EXPECT().Close().Return(nil).AnyTimes()
-
-		agentConnFn := func(_ context.Context, agentID uuid.UUID) (workspacesdk.AgentConn, func(), error) {
-			require.Equal(t, expectedAgentID, agentID)
-			return mockConn, func() {}, nil
-		}
-
-		logger := slogtest.Make(t, &slogtest.Options{IgnoreErrors: true})
-		server := chatd.New(chatd.Config{
-			Logger:                     logger,
-			Database:                   db,
-			ReplicaID:                  uuid.New(),
-			Pubsub:                     ps,
-			AgentConn:                  agentConnFn,
-			PendingChatAcquireInterval: 10 * time.Millisecond,
-			InFlightChatStaleAfter:     testutil.WaitSuperLong,
-		})
-		t.Cleanup(func() {
-			require.NoError(t, server.Close())
-		})
-
-		// Create a chat without a parent — the ancestor header
-		// should contain an empty JSON array.
-		chat, err := server.CreateChat(ctx, chatd.CreateOptions{
-			OwnerID:       user.ID,
-			WorkspaceID:   uuid.NullUUID{UUID: workspaceID, Valid: true},
-			Title:         "header-injection-no-parent",
-			ModelConfigID: model.ID,
-			InitialUserContent: []fantasy.Content{
-				fantasy.TextContent{Text: "hello"},
-			},
-		})
-		require.NoError(t, err)
-
-		select {
-		case <-headersCaptured:
-		case <-ctx.Done():
-			require.FailNow(t, "timed out waiting for SetExtraHeaders")
-		}
-
-		require.Equal(t,
-			chat.ID.String(),
-			capturedHeaders.Get(workspacesdk.CoderChatIDHeader),
-		)
-
-		// When there is no parent, the code declares
-		// var ancestorIDs []string and never appends to it,
-		// so json.Marshal produces "null".
-		ancestorJSON := capturedHeaders.Get(workspacesdk.CoderAncestorChatIDsHeader)
-		var ancestorIDs []string
-		err = json.Unmarshal([]byte(ancestorJSON), &ancestorIDs)
-		require.NoError(t, err)
-		require.Empty(t, ancestorIDs)
-	})
-}

coderd/chatd/chatloop/chatloop.go

@@ -73,7 +73,9 @@ type RunOptions struct {
 	// OnRetry is called before each retry attempt when the LLM
 	// stream fails with a retryable error. It provides the attempt
 	// number, error, and backoff delay so callers can publish status
-	// events to connected clients.
+	// events to connected clients. Callers should also clear any
+	// buffered stream state from the failed attempt in this callback
+	// to avoid sending duplicated content.
 	OnRetry chatretry.OnRetryFn
 
 	OnInterruptedPersistError func(error)
@@ -209,6 +211,10 @@ func Run(ctx context.Context, opts RunOptions) error {
 	var lastUsage fantasy.Usage
 	var lastProviderMetadata fantasy.ProviderMetadata
 
+	totalSteps := 0
+	// When totalSteps reaches MaxSteps the inner loop exits immediately
+	// (its condition is false), stoppedByModel stays false, and the
+	// post-loop guard breaks the outer compaction loop.
 	for compactionAttempt := 0; ; compactionAttempt++ {
 		alreadyCompacted := false
 		// stoppedByModel is true when the inner step loop
@@ -222,7 +228,8 @@ func Run(ctx context.Context, opts RunOptions) error {
 		// agent never had a chance to use the compacted context.
 		compactedOnFinalStep := false
 
-		for step := 0; step < opts.MaxSteps; step++ {
+		for step := 0; totalSteps < opts.MaxSteps; step++ {
+			totalSteps++
 			// Copy messages so that provider-specific caching
 			// mutations don't leak back to the caller's slice.
 			// copy copies Message structs by value, so field
@@ -321,6 +328,12 @@ func Run(ctx context.Context, opts RunOptions) error {
 			lastUsage = result.usage
 			lastProviderMetadata = result.providerMetadata
 
+			// Append the step's response messages so that both
+			// inline and post-loop compaction see the full
+			// conversation including the latest assistant reply.
+			stepMessages := result.toResponseMessages()
+			messages = append(messages, stepMessages...)
+
 			// Inline compaction.
 			if opts.Compaction != nil && opts.ReloadMessages != nil {
 				did, compactErr := tryCompact(
@@ -354,17 +367,11 @@ func Run(ctx context.Context, opts RunOptions) error {
 			// The agent is continuing with tool calls, so any
 			// prior compaction has already been consumed.
 			compactedOnFinalStep = false
-
-			// Build messages from the step for the next iteration.
-			// toResponseMessages produces assistant-role content
-			// (text, reasoning, tool calls) and tool-result content.
-			stepMessages := result.toResponseMessages()
-			messages = append(messages, stepMessages...)
 		}
 
 		// Post-run compaction safety net: if we never compacted
 		// during the loop, try once at the end.
-		if !alreadyCompacted && opts.Compaction != nil {
+		if !alreadyCompacted && opts.Compaction != nil && opts.ReloadMessages != nil {
 			did, err := tryCompact(
 				ctx,
 				opts.Model,
@@ -383,7 +390,6 @@ func Run(ctx context.Context, opts RunOptions) error {
 				compactedOnFinalStep = true
 			}
 		}
-
 		// Re-enter the step loop when compaction fired on the
 		// model's final step. This lets the agent continue
 		// working with fresh summarized context instead of
@@ -514,7 +520,6 @@ func processStepStream(
 					})
 				}
 			}
-
 		case fantasy.StreamPartTypeToolInputStart:
 			activeToolCalls[part.ID] = &fantasy.ToolCallContent{
 				ToolCallID:       part.ID,

coderd/chatd/chatloop/compaction.go

@@ -123,7 +123,8 @@ func tryCompact(
 		config.SystemSummaryPrefix + "\n\n" + summary,
 	)
 
-	err = config.Persist(ctx, CompactionResult{
+	persistCtx := context.WithoutCancel(ctx)
+	err = config.Persist(persistCtx, CompactionResult{
 		SystemSummary:    systemSummary,
 		SummaryReport:    summary,
 		ThresholdPercent: config.ThresholdPercent,

coderd/chatd/chatloop/compaction_test.go

@@ -76,9 +76,20 @@ func TestRun_Compaction(t *testing.T) {
 					return nil
 				},
 			},
+			ReloadMessages: func(_ context.Context) ([]fantasy.Message, error) {
+				return []fantasy.Message{
+					textMessage(fantasy.MessageRoleUser, "hello"),
+				}, nil
+			},
 		})
 		require.NoError(t, err)
-		require.Equal(t, 1, persistCompactionCalls)
+		// Compaction fires twice: once inline when the threshold is
+		// reached on step 0 (the only step, since MaxSteps=1), and
+		// once from the post-run safety net during the re-entry
+		// iteration (where totalSteps already equals MaxSteps so the
+		// inner loop doesn't execute, but lastUsage still exceeds
+		// the threshold).
+		require.Equal(t, 2, persistCompactionCalls)
 		require.Contains(t, persistedCompaction.SystemSummary, summaryText)
 		require.Equal(t, summaryText, persistedCompaction.SummaryReport)
 		require.Equal(t, int64(80), persistedCompaction.ContextTokens)
@@ -151,13 +162,25 @@ func TestRun_Compaction(t *testing.T) {
 					return nil
 				},
 			},
+			ReloadMessages: func(_ context.Context) ([]fantasy.Message, error) {
+				return []fantasy.Message{
+					textMessage(fantasy.MessageRoleUser, "hello"),
+				}, nil
+			},
 		})
 		require.NoError(t, err)
+		// Compaction fires twice (see PersistsWhenThresholdReached
+		// for the full explanation). Each cycle follows the order:
+		// publish_tool_call → generate → persist → publish_tool_result.
 		require.Equal(t, []string{
 			"publish_tool_call",
 			"generate",
 			"persist",
 			"publish_tool_result",
+			"publish_tool_call",
+			"generate",
+			"persist",
+			"publish_tool_result",
 		}, callOrder)
 	})
 
@@ -457,6 +480,11 @@ func TestRun_Compaction(t *testing.T) {
 					compactionErr = err
 				},
 			},
+			ReloadMessages: func(_ context.Context) ([]fantasy.Message, error) {
+				return []fantasy.Message{
+					textMessage(fantasy.MessageRoleUser, "hello"),
+				}, nil
+			},
 		})
 		require.NoError(t, err)
 		require.Error(t, compactionErr)

coderd/chatd/chatretry/chatretry.go

@@ -8,6 +8,8 @@ import (
 	"errors"
 	"strings"
 	"time"
+
+	"golang.org/x/xerrors"
 )
 
 const (
@@ -18,6 +20,12 @@ const (
 	// MaxDelay is the upper bound for the exponential backoff
 	// duration. Matches the cap used in coder/mux.
 	MaxDelay = 60 * time.Second
+
+	// MaxAttempts is the upper bound on retry attempts before
+	// giving up. With a 60s max backoff this allows roughly
+	// 25 minutes of retries, which is reasonable for transient
+	// LLM provider issues.
+	MaxAttempts = 25
 )
 
 // nonRetryablePatterns are substrings that indicate a permanent error
@@ -131,9 +139,8 @@ type RetryFn func(ctx context.Context) error
 type OnRetryFn func(attempt int, err error, delay time.Duration)
 
 // Retry calls fn repeatedly until it succeeds, returns a
-// non-retryable error, or ctx is canceled. There is no max attempt
-// limit — retries continue indefinitely with exponential backoff
-// (capped at 60s), matching the behavior of coder/mux.
+// non-retryable error, ctx is canceled, or MaxAttempts is reached.
+// Retries use exponential backoff capped at MaxDelay.
 //
 // The onRetry callback (if non-nil) is called before each retry
 // attempt, giving the caller a chance to reset state, log, or
@@ -156,10 +163,15 @@ func Retry(ctx context.Context, fn RetryFn, onRetry OnRetryFn) error {
 			return ctx.Err()
 		}
 
-		delay := Delay(attempt)
+		attempt++
+		if attempt >= MaxAttempts {
+			return xerrors.Errorf("max retry attempts (%d) exceeded: %w", MaxAttempts, err)
+		}
+
+		delay := Delay(attempt - 1)
 
 		if onRetry != nil {
-			onRetry(attempt+1, err, delay)
+			onRetry(attempt, err, delay)
 		}
 
 		timer := time.NewTimer(delay)
@@ -169,7 +181,5 @@ func Retry(ctx context.Context, fn RetryFn, onRetry OnRetryFn) error {
 			return ctx.Err()
 		case <-timer.C:
 		}
-
-		attempt++
 	}
 }