Scheduled/background task sessions hang on their 2nd shell command (desktop app, Windows 11)

Preflight Checklist

• [x] I have searched existing issues and this hasn't been reported yet
• [x] This is a single bug report (please file separate reports for different bugs)
• [x] I am using the latest version of Claude Code

What's Wrong?

Since 6/30, every scheduled-task (routine) session in the desktop app freezes on an early Bash tool call — typically the 2nd command. The command never spawns an OS process, no result is returned, and the Bash tool's 2-minute timeout never fires; the session shows "running" forever. Interactive sessions on the same machine execute commands normally at the same time. A verified full app restart (all processes recreated) does not fix it — re-fired runs stall identically. Single-line commands sometimes succeed; multi-line/heredoc commands hang most reliably. Windows 11 Home, local (not cloud/dispatch) routines, project permissions include a blanket Bash allow.

What Should Happen?

Scheduled-task (routine) sessions should execute shell commands the same way interactive sessions do — the command spawns, returns a result, and if it ever hangs, the Bash tool's 2-minute timeout should fire instead of the session sitting in "running" forever.

Error Messages/Logs

No error output — the tool call simply never returns and no timeout fires.

Steps to Reproduce

1. On the Windows desktop app, create a scheduled task (routine) whose work requires running shell commands.
2. Let it fire on schedule, or press "Run now."
3. The session starts, produces its opening response, and executes its first simple one-line Bash command successfully.
4. On the 2nd Bash tool call (multi-line/heredoc commands reproduce most reliably), the session freezes: no OS process is created, no tool result is returned, no timeout fires, and the session shows "running" indefinitely.
5. Interactive sessions run the identical commands successfully on the same machine at the same time.

Observed on every scheduled run since 6/30 (5+ consecutive nights, 3 different tasks). Restarting the app (verified via process creation times) does not change the behavior.

Claude Model

None

Is this a regression?

Yes, this worked in a previous version

Last Working Version

Unknown version number — scheduled runs worked nightly through 6/29; first failure 6/30.

Claude Code Version

Desktop app 1.17377.2 (Windows, Microsoft Store build) — standalone claude CLI not installed

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Windows Terminal

Additional Information

Permissions are not the cause (project settings include a blanket Bash allow, and no permission prompt is shown in the stuck sessions). The machine has no WSL installed. Same symptom across 3 different scheduled tasks. Happy to provide session transcripts (.jsonl) on request — each ends with an assistant tool_use entry that never receives a tool_result.