[BUG] Cloud routine sessions "Complete" without ever processing the initial prompt message

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?

Created a scheduled cloud routine (Claude Code Routines / RemoteTrigger API) with an mcp_connections array (Slack + HubSpot connectors) and a job_config.ccr.session_context.events array containing one type: "user" message. Running the routine (both via manual run and via its cron schedule) consistently produces a run marked "Completed" with no errors in the dashboard — but the session transcript shows only:

• Set up a cloud container ✅
• Clone repository (skipped — no repo configured)
• Started Claude Code ✅

...and then nothing. No assistant turn, no tool call, no response to the initial user message at all.

Reproduction:

1. Create a routine with a minimal single-instruction prompt, e.g.: Call <slack tool> with channel_id X and message "test". Then stop.
2. Run it manually via RemoteTrigger action:"run".
3. Check the Slack channel — no message appears.
4. Open the run in the Claude Code UI → expand "Initialized session" → see only the three infra steps above, no conversation turn.

Tried on:

• An existing routine (trig_01RicpMsgK9623DdFR4WGcwU), across 4 separate runs with varying prompt complexity (from a full multi-step task down to one tool call).
• A brand-new routine created from scratch with the same trivial one-tool-call prompt (trig_012gSK1Ryy6r38B7jAypAK4h) — same result.

Expected: the session should process the initial user message and execute the requested tool call.

Actual: the session starts, launches Claude Code, and then idles/completes without ever acting on the prompt.

Environment: env_011iwoSfjCdN46RYYmbkPMQ6 (Default, anthropic_cloud), model claude-sonnet-5.

What Should Happen?

Created a scheduled cloud routine (Claude Code Routines / RemoteTrigger API) with an mcp_connections array (Slack + HubSpot connectors) and a job_config.ccr.session_context.events array containing one type: "user" message. Running the routine (both via manual run and via its cron schedule) consistently produces a run marked "Completed" with no errors in the dashboard — but the session transcript shows only:

• Set up a cloud container ✅
• Clone repository (skipped — no repo configured)
• Started Claude Code ✅

...and then nothing. No assistant turn, no tool call, no response to the initial user message at all.

Tried on:

• An existing routine (trig_01RicpMsgK9623DdFR4WGcwU), across 4 separate runs with varying prompt complexity (from a full multi-step task down to one tool call).
• A brand-new routine created from scratch with the same trivial one-tool-call prompt (trig_012gSK1Ryy6r38B7jAypAK4h) — same result.

Expected: the session should process the initial user message and execute the requested tool call.

Actual: the session starts, launches Claude Code, and then idles/completes without ever acting on the prompt.

Environment: env_011iwoSfjCdN46RYYmbkPMQ6 (Default, anthropic_cloud), model claude-sonnet-5.

Error Messages/Logs

Steps to Reproduce

Reproduction:

1. Create a routine with a minimal single-instruction prompt, e.g.: Call <slack tool> with channel_id X and message "test". Then stop.
2. Run it manually via RemoteTrigger action:"run".
3. Check the Slack channel — no message appears.
4. Open the run in the Claude Code UI → expand "Initialized session" → see only the three infra steps above, no conversation turn.

Claude Model

Sonnet (default)

Is this a regression?

I don't know

Last Working Version

_No response_

Claude Code Version

5

Platform

Other

Operating System

macOS

Terminal/Shell

Terminal.app (macOS)

Additional Information

_No response_