FIX: Sending Queued Messages Lost When Clicking "Send Now" During Streaming

src/main/lib/trpc/routers/claude.ts

@@ -1504,7 +1504,7 @@ ${prompt}
 
                 // When result arrives, assign the last assistant UUID to metadata
                 // It will be emitted as part of the merged message-metadata chunk below
-                if (msgAny.type === "result" && historyEnabled && lastAssistantUuid) {
+                if (msgAny.type === "result" && historyEnabled && lastAssistantUuid && !abortController.signal.aborted) {
                   metadata.sdkMessageUuid = lastAssistantUuid
                 }
 
@@ -1832,6 +1832,8 @@ ${prompt}
               parts.push({ type: "text", text: currentText })
             }
 
+            const savedSessionId = metadata.sessionId
+
             if (parts.length > 0) {
               const assistantMessage = {
                 id: crypto.randomUUID(),
@@ -1845,7 +1847,7 @@ ${prompt}
               db.update(subChats)
                 .set({
                   messages: JSON.stringify(finalMessages),
-                  sessionId: metadata.sessionId,
+                  sessionId: savedSessionId,
                   streamId: null,
                   updatedAt: new Date(),
                 })
@@ -1855,7 +1857,7 @@ ${prompt}
               // No assistant response - just clear streamId
               db.update(subChats)
                 .set({
-                  sessionId: metadata.sessionId,
+                  sessionId: savedSessionId,
                   streamId: null,
                   updatedAt: new Date(),
                 })
@@ -1896,14 +1898,13 @@ ${prompt}
           activeSessions.delete(input.subChatId)
           clearPendingApprovals("Session ended.", input.subChatId)
 
-          // Save sessionId on abort so conversation can be resumed
-          // Clear streamId since we're no longer streaming
+          // Clear streamId since we're no longer streaming.
+          // sessionId is NOT saved here — the save block in the async function
+          // handles it (saves on normal completion, clears on abort). This avoids
+          // a redundant DB write that the cancel mutation would then overwrite.
           const db = getDatabase()
           db.update(subChats)
-            .set({
-              streamId: null,
-              ...(currentSessionId && { sessionId: currentSessionId })
-            })
+            .set({ streamId: null })
             .where(eq(subChats.id, input.subChatId))
             .run()
         }
@@ -1964,9 +1965,10 @@ ${prompt}
         controller.abort()
         activeSessions.delete(input.subChatId)
         clearPendingApprovals("Session cancelled.", input.subChatId)
-        return { cancelled: true }
       }
-      return { cancelled: false }
+
+
+      return { cancelled: !!controller }
     }),
 
   /**

src/renderer/features/agents/lib/ipc-chat-transport.ts

@@ -24,6 +24,7 @@ import {
   pendingUserQuestionsAtom,
 } from "../atoms"
 import { useAgentSubChatStore } from "../stores/sub-chat-store"
+import type { AgentMessageMetadata } from "../ui/agent-message-usage"
 
 // Error categories and their user-friendly messages
 const ERROR_TOAST_CONFIG: Record<
@@ -149,11 +150,13 @@ export class IPCChatTransport implements ChatTransport<UIMessage> {
     const prompt = this.extractText(lastUser)
     const images = this.extractImages(lastUser)
 
-    // Get sessionId for resume
+    // Get sessionId for resume (server preserves sessionId on abort so
+    // the next message can resume with full conversation context)
     const lastAssistant = [...options.messages]
       .reverse()
       .find((m) => m.role === "assistant")
-    const sessionId = (lastAssistant as any)?.metadata?.sessionId
+    const metadata = lastAssistant?.metadata as AgentMessageMetadata | undefined
+    const sessionId = metadata?.sessionId
 
     // Read extended thinking setting dynamically (so toggle applies to existing chats)
     const thinkingEnabled = appStore.get(extendedThinkingEnabledAtom)
@@ -441,7 +444,6 @@ export class IPCChatTransport implements ChatTransport<UIMessage> {
         options.abortSignal?.addEventListener("abort", () => {
           console.log(`[SD] R:ABORT sub=${subId} n=${chunkCount} last=${lastChunkType}`)
           sub.unsubscribe()
-          trpcClient.claude.cancel.mutate({ subChatId: this.config.subChatId })
           try {
             controller.close()
           } catch {

src/renderer/features/agents/main/active-chat.tsx

@@ -222,6 +222,39 @@ function utf8ToBase64(str: string): string {
   return btoa(binString)
 }
 
+/** Wait for streaming to finish by subscribing to the status store.
+ *  Includes a 30s safety timeout — if the store never transitions to "ready",
+ *  the promise resolves anyway to prevent hanging the UI indefinitely. */
+const STREAMING_READY_TIMEOUT_MS = 30_000
+
+function waitForStreamingReady(subChatId: string): Promise<void> {
+  return new Promise((resolve) => {
+    if (!useStreamingStatusStore.getState().isStreaming(subChatId)) {
+      resolve()
+      return
+    }
+
+    const timeout = setTimeout(() => {
+      console.warn(
+        `[waitForStreamingReady] Timed out after ${STREAMING_READY_TIMEOUT_MS}ms for subChat ${subChatId.slice(-8)}, proceeding anyway`
+      )
+      unsub()
+      resolve()
+    }, STREAMING_READY_TIMEOUT_MS)
+
+    const unsub = useStreamingStatusStore.subscribe(
+      (state) => state.statuses[subChatId],
+      (status) => {
+        if (status === "ready" || status === undefined) {
+          clearTimeout(timeout)
+          unsub()
+          resolve()
+        }
+      }
+    )
+  })
+}
+
 // Exploring tools - these get grouped when 2+ consecutive
 const EXPLORING_TOOLS = new Set([
   "tool-Read",
@@ -2326,11 +2359,6 @@ const ChatViewInner = memo(function ChatViewInner({
     // Mark as manually aborted to prevent completion sound
     agentChatStore.setManuallyAborted(subChatId, true)
     await stopRef.current()
-    // Call DELETE endpoint to cancel server-side stream
-    await fetch(
-      `/api/agents/chat?id=${encodeURIComponent(subChatId)}`,
-      { method: "DELETE", credentials: "include" },
-    )
   }, [subChatId])
 
   // Wrapper for addTextContext that handles TextSelectionSource
@@ -3078,11 +3106,6 @@ const ChatViewInner = memo(function ChatViewInner({
         // Mark as manually aborted to prevent completion sound
         agentChatStore.setManuallyAborted(subChatId, true)
         await stop()
-        // Call DELETE endpoint to cancel server-side stream
-        await fetch(`/api/agents/chat?id=${encodeURIComponent(subChatId)}`, {
-          method: "DELETE",
-          credentials: "include",
-        })
       }
     }
 
@@ -3504,82 +3527,83 @@ const ChatViewInner = memo(function ChatViewInner({
     const item = popItemFromQueue(subChatId, itemId)
     if (!item) return
 
-    // Stop current stream if streaming and wait for status to become ready
-    if (isStreamingRef.current) {
-      await handleStop()
-      // Wait for status to become "ready" (max 2 seconds)
-      const maxWait = 2000
-      const pollInterval = 50
-      let waited = 0
-      while (isStreamingRef.current && waited < maxWait) {
-        await new Promise((resolve) => setTimeout(resolve, pollInterval))
-        waited += pollInterval
+    try {
+      // Stop current stream if streaming and wait for status to become ready.
+      // The server-side save block preserves sessionId on abort, so the next
+      // message can resume the session with full conversation context.
+      if (isStreamingRef.current) {
+        await handleStop()
+        await waitForStreamingReady(subChatId)
       }
-    }
 
-    // Build message parts from queued item
-    const parts: any[] = [
-      ...(item.images || []).map((img) => ({
-        type: "data-image" as const,
-        data: {
-          url: img.url,
-          mediaType: img.mediaType,
-          filename: img.filename,
-          base64Data: img.base64Data,
-        },
-      })),
-      ...(item.files || []).map((f) => ({
-        type: "data-file" as const,
-        data: {
-          url: f.url,
-          mediaType: f.mediaType,
-          filename: f.filename,
-          size: f.size,
-        },
-      })),
-    ]
-
-    // Add text contexts as mention tokens
-    let mentionPrefix = ""
-    if (item.textContexts && item.textContexts.length > 0) {
-      const quoteMentions = item.textContexts.map((tc) => {
-        const preview = tc.text.slice(0, 50).replace(/[:\[\]]/g, "") // Create and sanitize preview
-        const encodedText = utf8ToBase64(tc.text) // Base64 encode full text
-        return `@[${MENTION_PREFIXES.QUOTE}${preview}:${encodedText}]`
-      })
-      mentionPrefix = quoteMentions.join(" ") + " "
-    }
+      // Build message parts from queued item
+      const parts: any[] = [
+        ...(item.images || []).map((img) => ({
+          type: "data-image" as const,
+          data: {
+            url: img.url,
+            mediaType: img.mediaType,
+            filename: img.filename,
+            base64Data: img.base64Data,
+          },
+        })),
+        ...(item.files || []).map((f) => ({
+          type: "data-file" as const,
+          data: {
+            url: f.url,
+            mediaType: f.mediaType,
+            filename: f.filename,
+            size: f.size,
+          },
+        })),
+      ]
+
+      // Add text contexts as mention tokens
+      let mentionPrefix = ""
+      if (item.textContexts && item.textContexts.length > 0) {
+        const quoteMentions = item.textContexts.map((tc) => {
+          const preview = tc.text.slice(0, 50).replace(/[:\[\]]/g, "") // Create and sanitize preview
+          const encodedText = utf8ToBase64(tc.text) // Base64 encode full text
+          return `@[${MENTION_PREFIXES.QUOTE}${preview}:${encodedText}]`
+        })
+        mentionPrefix = quoteMentions.join(" ") + " "
+      }
 
-    // Add diff text contexts as mention tokens
-    if (item.diffTextContexts && item.diffTextContexts.length > 0) {
-      const diffMentions = item.diffTextContexts.map((dtc) => {
-        const preview = dtc.text.slice(0, 50).replace(/[:\[\]]/g, "") // Create and sanitize preview
-        const encodedText = utf8ToBase64(dtc.text) // Base64 encode full text
-        const lineNum = dtc.lineNumber || 0
-        return `@[${MENTION_PREFIXES.DIFF}${dtc.filePath}:${lineNum}:${preview}:${encodedText}]`
-      })
-      mentionPrefix += diffMentions.join(" ") + " "
-    }
+      // Add diff text contexts as mention tokens
+      if (item.diffTextContexts && item.diffTextContexts.length > 0) {
+        const diffMentions = item.diffTextContexts.map((dtc) => {
+          const preview = dtc.text.slice(0, 50).replace(/[:\[\]]/g, "") // Create and sanitize preview
+          const encodedText = utf8ToBase64(dtc.text) // Base64 encode full text
+          const lineNum = dtc.lineNumber || 0
+          return `@[${MENTION_PREFIXES.DIFF}${dtc.filePath}:${lineNum}:${preview}:${encodedText}]`
+        })
+        mentionPrefix += diffMentions.join(" ") + " "
+      }
 
-    if (item.message || mentionPrefix) {
-      parts.push({ type: "text", text: mentionPrefix + (item.message || "") })
-    }
+      if (item.message || mentionPrefix) {
+        parts.push({ type: "text", text: mentionPrefix + (item.message || "") })
+      }
 
-    // Track message sent
-    trackMessageSent({
-      workspaceId: subChatId,
-      messageLength: item.message.length,
-      mode: subChatModeRef.current,
-    })
+      // Track message sent
+      trackMessageSent({
+        workspaceId: subChatId,
+        messageLength: item.message.length,
+        mode: subChatModeRef.current,
+      })
 
-    // Update timestamps
-    useAgentSubChatStore.getState().updateSubChatTimestamp(subChatId)
+      // Update timestamps
+      useAgentSubChatStore.getState().updateSubChatTimestamp(subChatId)
 
-    // Enable auto-scroll and immediately scroll to bottom
-    shouldAutoScrollRef.current = true
-    scrollToBottom()
+      // Enable auto-scroll and immediately scroll to bottom
+      shouldAutoScrollRef.current = true
+      scrollToBottom()
 
-    await sendMessageRef.current({ role: "user", parts })
+      await sendMessageRef.current({ role: "user", parts })
+    } catch (error) {
+      console.error("[handleSendFromQueue] Error sending queued message:", error)
+      // Requeue the item at the front so it isn't lost
+      useMessageQueueStore.getState().prependItem(subChatId, item)
+    }
   }, [subChatId, popItemFromQueue, handleStop])
 
   const handleRemoveFromQueue = useCallback((itemId: string) => {
@@ -3603,17 +3627,12 @@ const ChatViewInner = memo(function ChatViewInner({
 
     if (!hasText && !hasImages) return
 
-    // Stop current stream if streaming and wait for status to become ready
+    // Stop current stream if streaming and wait for status to become ready.
+    // The server-side save block sets sessionId=null on abort, so the next
+    // message starts fresh without needing an explicit cancel mutation.
     if (isStreamingRef.current) {
       await handleStop()
-      // Wait for status to become "ready" (max 2 seconds)
-      const maxWait = 2000
-      const pollInterval = 50
-      let waited = 0
-      while (isStreamingRef.current && waited < maxWait) {
-        await new Promise((resolve) => setTimeout(resolve, pollInterval))
-        waited += pollInterval
-      }
+      await waitForStreamingReady(subChatId)
     }
 
     // Auto-restore archived workspace when sending a message
@@ -3704,7 +3723,13 @@ const ChatViewInner = memo(function ChatViewInner({
     shouldAutoScrollRef.current = true
     scrollToBottom()
 
-    await sendMessageRef.current({ role: "user", parts })
+    try {
+      await sendMessageRef.current({ role: "user", parts })
+    } catch (error) {
+      console.error("[handleForceSend] Error sending message:", error)
+      // Restore editor content so the user can retry
+      editorRef.current?.setValue(finalText)
+    }
   }, [
     sandboxSetupStatus,
     isArchived,

src/renderer/features/agents/main/chat-input-area.tsx

@@ -181,7 +181,9 @@ function arePropsEqual(prevProps: ChatInputAreaProps, nextProps: ChatInputAreaPr
     prevProps.repository !== nextProps.repository ||
     prevProps.sandboxId !== nextProps.sandboxId ||
     prevProps.projectPath !== nextProps.projectPath ||
-    prevProps.isMobile !== nextProps.isMobile
+    prevProps.isMobile !== nextProps.isMobile ||
+    prevProps.queueLength !== nextProps.queueLength ||
+    prevProps.firstQueueItemId !== nextProps.firstQueueItemId
   ) {
     return false
   }
@@ -209,7 +211,8 @@ function arePropsEqual(prevProps: ChatInputAreaProps, nextProps: ChatInputAreaPr
     prevProps.onRemovePastedText !== nextProps.onRemovePastedText ||
     prevProps.onCacheFileContent !== nextProps.onCacheFileContent ||
     prevProps.onInputContentChange !== nextProps.onInputContentChange ||
-    prevProps.onSubmitWithQuestionAnswer !== nextProps.onSubmitWithQuestionAnswer
+    prevProps.onSubmitWithQuestionAnswer !== nextProps.onSubmitWithQuestionAnswer ||
+    prevProps.onSendFromQueue !== nextProps.onSendFromQueue
   ) {
     return false
   }