using-ask-question-cli

name	Using ask-question CLI
description	Send prompts to ChatGPT via browser automation. Use this when you need to query ChatGPT from the command line or integrate with the /ask-question slash command.
allowed-tools	["Bash","Read"]

Using ask-question CLI

Send prompts to ChatGPT via Playwright browser automation with headless operation.

Architecture

ask-question CLI ──► HTTP POST /ask ──► ask-question-server (daemon)
                                              │
                                              ▼
                                        Chromium (headless)
                                        + storageState session
                                              │
                                              ▼
                                        ChatGPT response

Prerequisites

1. Node.js installed
2. Playwright dependencies installed with npm install
3. Repo devenv/direnv shell active so local ask-question* commands are on PATH

Setup (One-Time)

cd ~/Code/chatgpt-relay
npm install
ask-question-login  # Opens browser, log into ChatGPT

Do not use npm link in the Nix/devenv setup. The repo provides local devenv wrappers for ask-question, ask-question-server, and ask-question-login. If the shell is not already activated, run commands as devenv shell -- ask-question-login.

Starting the Daemon

cd ~/Code/chatgpt-relay
npm run server:log

Keep this running in a dedicated terminal or tmux pane. It runs headless (no visible browser).

Why tee to a log file? This allows Claude Code to check logs via tail ~/.local/state/chatgpt-relay/daemon.log even when the daemon runs in a separate terminal.

Expected output:

[ask-question-server] Starting headless browser...
[ask-question-server] Using session: ~/.chatgpt-relay/storage-state.json
[ask-question-server] ChatGPT page opened.
[ask-question-server] Login verified.
[ask-question-server] HTTP server listening on http://127.0.0.1:3033

Usage

Direct prompt

ask-question "What is the capital of France?"

From file

ask-question -f question.md -o answer.md

Pipe input

echo "Explain async/await in JavaScript" | ask-question

Options

Option	Description
-f, --file <path>	Read prompt from file
-o, --output <path>	Write response to file
-t, --timeout <ms>	Response timeout (default: 1200000 / 20 min)
--continue	Continue existing chat (default: start new chat)
-h, --help	Show help

Integration with /ask-question Slash Command

The /ask-question slash command in Claude Code uses this CLI:

1. Claude drafts a Stack Exchange-formatted question
2. Claude invokes: ask-question -f question.md -o answer.md
3. CLI blocks while ChatGPT responds (typically 1-10 minutes)
4. Claude reads the answer file and discusses

Use /ask-question draft topic to skip automation and just draft the question.

Troubleshooting

"Server not running or not responding"

Start the daemon:

ask-question-server

"No session found"

Run login helper:

ask-question-login

Session expired

ChatGPT sessions expire after a while. Re-run login:

ask-question-login

Response timeout

Default is 20 minutes. Adjust if needed:

# Shorter timeout for quick questions
ask-question -t 120000 "What is 2+2?"

# Longer timeout for complex responses
ask-question -t 1800000 "Write a comprehensive analysis..."

Debugging

Request ID Tracing

Each request gets a unique ID (e.g., [a1b2c3d4]) logged on both CLI and server sides:

[ask-question] [a1b2c3d4] Attempt 1/2...
[ask-question-server] [a1b2c3d4] Received (500 chars)
[ask-question-server] [a1b2c3d4] Processing...
[ask-question-server] [a1b2c3d4] Sending response (1200 chars)
[ask-question] [a1b2c3d4] Success

Use this to correlate CLI errors with server logs.

Connection Failures

The CLI automatically retries once on connection errors (fetch failed, ECONNREFUSED, etc.). If you see:

[ask-question] [a1b2c3d4] Error: fetch failed
[ask-question] [a1b2c3d4] Cause: ...
[ask-question] [a1b2c3d4] Cause code: UND_ERR_HEADERS_TIMEOUT

This indicates Undici's internal timeout fired. The CLI will retry automatically.

Environment Variables

Variable	Default	Description
ASK_QUESTION_SERVER_URL	http://127.0.0.1:3033	Server URL
ASK_QUESTION_PORT	3033	Server port
ASK_QUESTION_STORAGE_STATE_FILE	~/.chatgpt-relay/storage-state.json	Session file

Files

Path	Purpose
~/.chatgpt-relay/storage-state.json	Saved ChatGPT session (cookies/localStorage)

Architecture Deep Dive

Components

┌─────────────────────────────────────────────────────────────────────────┐
│  Claude Code                                                            │
│      │                                                                  │
│      ▼                                                                  │
│  /ask-question (slash command)                                          │
│      │                                                                  │
│      ▼                                                                  │
│  CLI (ask-question) ─► HTTP POST /ask ─► ask-question-server (daemon)   │
│                                               │                         │
│                                               ▼                         │
│                                         Chromium (headless)             │
│                                         + storageState session          │
│                                               │                         │
│                                               ▼                         │
│                                         ChatGPT tab                     │
│                                         (DOM automation)                │
└─────────────────────────────────────────────────────────────────────────┘

Design Decisions

HTTP Daemon over WebSocket Connect

• launchServer() doesn't support persistent sessions
• HTTP is curl-debuggable and simpler
• Request queue handles serialization naturally
• Browser runs headless (no focus-stealing)

Headless with StorageState

• ask-question-login: One-time headed browser for manual login, saves cookies
• ask-question-server: Headless browser loads saved session
• Session persists across server restarts

Reliability Features

Feature	Description
Request ID Tracing	8-char ID correlates CLI and server logs
Automatic Retry	CLI retries once on connection failures
Network Failure Detection	Tracks streaming response via response.finished()
Hard Reset on Errors	Closes and recreates page on failure
Login Verification	Server verifies login state at startup

Fragile Components (Maintenance Required)

These rely on ChatGPT's DOM structure and may break when ChatGPT updates their UI:

• Composer selectors (div[contenteditable], #prompt-textarea)
• Send button selectors (button[data-testid="send-button"])
• Message extraction (copy button, innerText fallback)
• Login detection (chat history panel visibility)
• Stop button lifecycle (generation progress)

Mitigation: Multiple selector fallbacks, semantic selectors where possible, clear error messages.