[BUG] Send Message to Proceed While Running Hangs Roo

[Jerrill]

Problem (one or two sentences)

When Roo launches an app (directly or via a script) we are shown the Proceed While Running and Kill Command button while Roo waits for the process to complete. We are allowed to enter a message and click send, but at that point Roo hangs will all inputs disabled.

Context (who is affected and when)

Everyone who wants to collab with Roo on a running background launched via the terminal.

Reproduction steps

Create an app or script that does something interesting (e.g. starts a web app) and have Roo launch it. Do not click on the Proceed While Running button, but rather type a message (e.g. Let's launch a browser and take a look at that together!) and click the send button. All inputs are disabled and Roo hangs.

Workaround/Recovery from this state:
To recover you have to click the New Task button to close the session, then come back into the session. You'll find now a Resume Task button and the message controls are enabled. Type the message again because it's not in the history. Click Send.

Expected result

Roo proceeds while the task is running and receives the message and the message is stored in the message history.

Actual result

The Roo harness hangs requiring the workaround described above

Variations tried (optional)

No response

App Version

3.37.1

API Provider (optional)

Not Applicable / Other

Model Used (optional)

Claude Opus 4.5, but I think it's any of them

Roo Code Task Links (optional)

No response

Relevant logs or errors (optional)

[roomote]

I've analyzed this issue and here's my proposed implementation plan:

Root Cause Analysis

The bug occurs due to a state management issue in the webview UI when a user sends a message during the command_output ask state (while a long-running command is executing).

The flow that causes the hang:

1. User runs a long-running command (e.g., npm run dev)
2. Command produces output, triggering task.ask("command_output", "") in ExecuteCommandTool.ts
3. UI shows "Proceed While Running" and "Kill Command" buttons with sendingDisabled: false
4. User types a message and clicks send
5. handleSendMessage() in ChatView.tsx sends askResponse: "messageResponse"
6. Critical: handleChatReset() is called, which sets:
   • sendingDisabled: true
   • clineAsk: undefined
   • enableButtons: false
7. Backend receives the message and resolves the ask
8. In ExecuteCommandTool.ts, runInBackground is set to true, so no new command_output ask is sent
9. Result: UI remains disabled because no new message arrives to re-enable it

Why buttons work but messages don't:

When clicking "Proceed While Running", it sends terminalOperation: "continue" which is handled differently - it doesn't resolve the ask, so the command continues and can still send new asks. But when sending a message, the ask is resolved and runInBackground prevents new asks.

Proposed Fix

Modify handleSendMessage() in webview-ui/src/components/chat/ChatView.tsx to handle command_output specially:

For command_output, instead of sending an askResponse and calling handleChatReset(), we should:

1. Send the user's message via terminalOperation with the text included
2. Keep the UI in a responsive state (don't call handleChatReset())

This requires:

1. Modify ChatView.tsx - In handleSendMessage(), add special handling for command_output that sends a terminalOperation message with the user's text instead of an askResponse
2. Modify webviewMessageHandler.ts - Update the terminalOperation handler to accept and forward user text
3. Modify Task.ts - Update handleTerminalOperation() to handle user messages and forward them to the terminal process

This approach will:

• Keep the UI responsive after sending a message during command execution
• Allow the user to send multiple messages to stdin if needed
• Maintain consistency with how the "Proceed While Running" button works

Please mention @roomote in a comment saying that you approve this plan, and I'll proceed with the implementation.

[mrubens]

Hey Jerrill, thanks for the bug report! Are you using the inline terminal in the extension or the vs code terminal?

[Jerrill]

VSCode terminal. "Use Inline Terminal" is unchecked in settings.