[BUG] : Routine is not working properly in Claude Paid version

### Preflight Checklist

- [x] I have searched [existing issues](https://github.com/anthropics/claude-code/issues?q=is%3Aissue%20state%3Aopen%20label%3Abug) 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?

WHAT'S SET UP

- Daily Current Affairs Digest — trig_018zMjVfua9P1rQgTdMxmKfD — scheduled 19:20 IST daily, Hindi, sends to Discord + this email
- Nightly Quiz — trig_01DJaHSRfmymbyWH1cVaeEvs — scheduled 21:00 IST daily, Hindi, sends to Discord + this email
- Digest Watchdog — trig_012xToBRasFGkWaZceJ3UvAB — checks 19:40 IST, alerts only if digest didn't send
- Quiz Watchdog — trig_01Dz7rEKTJYRjrUSMH3s97Wy — checks 21:20 IST, alerts only if quiz didn't send

THE PROBLEM
None of the above are actually delivering right now. Every attempt today (5 out of 5 — 4 manual test runs plus one genuine scheduled cron fire at 13:50:41 UTC) hung on the platform side: the cloud session starts, logs "Claude Code process started," and then never processes the prompt — no tool calls, no output, indefinitely idle. This is not something fixable by changing the routine's configuration; it looks like a bug in Anthropic's cloud routine infrastructure itself.

Everything you've seen so far (the digest and quiz samples, in English and then Hindi) was generated and sent manually by me in a live chat session, not by the automated routines.

### What Should Happen?

It should be able to routinely send the details when desired, as no one will sit and hit manual things each time

### Error Messages/Logs

```shell

```

### Steps to Reproduce

WHAT'S SET UP
- Daily Current Affairs Digest — trig_018zMjVfua9P1rQgTdMxmKfD — scheduled 19:20 IST daily, Hindi, sends to Discord + this email
- Nightly Quiz — trig_01DJaHSRfmymbyWH1cVaeEvs — scheduled 21:00 IST daily, Hindi, sends to Discord + this email
- Digest Watchdog — trig_012xToBRasFGkWaZceJ3UvAB — checks 19:40 IST, alerts only if digest didn't send
- Quiz Watchdog — trig_01Dz7rEKTJYRjrUSMH3s97Wy — checks 21:20 IST, alerts only if quiz didn't send

THE PROBLEM
None of the above are actually delivering right now. Every attempt today (5 out of 5 — 4 manual test runs plus one genuine scheduled cron fire at 13:50:41 UTC) hung on the platform side: the cloud session starts, logs "Claude Code process started," and then never processes the prompt — no tool calls, no output, indefinitely idle. This is not something fixable by changing the routine's configuration; it looks like a bug in Anthropic's cloud routine infrastructure itself.

Everything you've seen so far (the digest and quiz samples, in English and then Hindi) was generated and sent manually by me in a live chat session, not by the automated routines.

### Claude Model

Sonnet (default)

### Is this a regression?

Yes, this worked in a previous version

### Last Working Version

_No response_

### Claude Code Version

2.1.238

### Platform

Anthropic API

### Operating System

macOS

### Terminal/Shell

Terminal.app (macOS)

### Additional Information

_No response_

The report names no repository files or tests. Start by reproducing a manual and scheduled routine with Claude Code 2.1.238 on macOS and inspect whether the cloud session stops after “Claude Code process started”; done when the routine processes its prompt and delivers the configured outputs.

Written by the indexing model from the issue text.