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

[jjjrmy]

Summary

• Fix bug where clicking "Send Now" on a queued message during streaming would pop the item from the queue but silently fail to send it, losing the message entirely
• Fix stale session ID race condition (SESSION_EXPIRED error) that occurred when aborting a stream and immediately starting a new message — the backend was resuming with an invalidated session ID saved by the cleanup handler
• Fix arePropsEqual in ChatInputArea missing queueLength, firstQueueItemId, and onSendFromQueue, causing stale closures when queue state changed

Changes

active-chat.tsx

• Add waitForStreamingReady() helper that subscribes to Zustand store instead of polling with setTimeout — includes a 30s safety timeout to prevent indefinite hangs
• Wrap handleSendFromQueue in try-catch; on failure, requeue the item via prependItem so it is never lost
• Wrap handleForceSend send call in try-catch; on failure, restore editor content via setValue so the user can retry
• Replace setTimeout polling loops in both handleSendFromQueue and handleForceSend with the event-driven waitForStreamingReady
• Remove dead fetch('/api/agents/chat') DELETE calls from handleStop and keyboard handler (no REST server exists in Electron)

ipc-chat-transport.ts

• Add sessionInvalidated flag set on abort to prevent the transport from reading a stale sessionId from the last assistant message's metadata
• Use typed AgentMessageMetadata cast instead of as any for metadata access
• Remove fire-and-forget cancel.mutate() from abort handler — session cleanup is now handled server-side

claude.ts

• Clear sessionId from DB on abort (sessionId: abortController.signal.aborted ? null : metadata.sessionId) in both the error catch block and normal save block
• Stop saving stale sessionId in the cleanup handler (unsubscribe callback) — only clear streamId
• Cancel mutation clears sessionId from DB when no active controller exists (handles the case where cleanup already removed from activeSessions)

chat-input-area.tsx

• Add queueLength, firstQueueItemId, and onSendFromQueue to arePropsEqual to prevent stale closures

Test plan

• Start a chat, send a message while AI is streaming, queue a second message
• Click "Send Now" on the queued message — verify the stream stops and the queued message is sent
• Verify no SESSION_EXPIRED error appears after the new message starts
• Verify that if send fails, the queued message reappears in the queue
• Verify force-send (Cmd+Enter while streaming) stops the stream and sends the new message
• Verify normal (non-interrupted) chat flow still works and sessions resume correctly

[jjjrmy]

Summary

• Fixes AI losing all conversation context when a queued message interrupts a streaming response
• The previous fix (6e246a0) cleared sessionId on abort to avoid resuming a dead session, but this caused the next message to start a completely fresh session with zero prior context since the Claude Code SDK relies solely on session ID-based resumption
• The session file on disk (~/.claude/) is still valid after abort — the actual issue was resumeSessionAt pointing to an incomplete message UUID, not the session itself

Changes

• Keep sessionId on abort instead of nulling it (both save paths in claude.ts)
• Guard sdkMessageUuid so it's not set on aborted streams — prevents resumeSessionAt from targeting an incomplete message
• Remove sessionInvalidated flag from client transport — no longer needed since server preserves the session
• Remove cancel mutation fallback that cleared sessionId from DB when no active controller existed
• Existing isSessionNotFound handler acts as safety net for genuinely stale sessions

Test plan

• Start a multi-turn conversation so there's meaningful context
• While the AI is streaming, type and send a new message (triggers queued message flow)
• Verify the AI's response to the queued message still has context of the prior conversation
• Verify normal (non-interrupted) conversations still work correctly
• Verify stopping a response and then sending a new message also preserves context