Cloud routine (RemoteTrigger/schedule) sessions hang indefinitely with zero transcript activity

Cloud routine (RemoteTrigger) sessions hang indefinitely with zero transcript activity

Summary

Scheduled Claude Code cloud routines (created via the /schedule skill / RemoteTrigger API) on my account intermittently start provisioning correctly but then hang forever: the session log shows only infrastructure events (sandbox allocation, repo clone, "Claude Code process started") and then nothing — no user-prompt processing, no tool calls, no assistant output — for many hours. This has now happened on 6 out of 6 attempts for one specific routine, across both genuine cron-scheduled fires and manually-forced fires, including a brand-new trigger created from scratch. Two other independent routines on the same account have separately shown related but different connectivity/tooling issues over the same ~5-day window, suggesting a broader platform instability rather than one broken trigger.

Account context

• Claude Pro account under frans@micon-it.nl (individual account, not an enterprise org)
• Cloud environment: a custom "Trusted"/Custom-network environment (env_01NR1Hmi2tPKHetyEDj6xiQH) with api.open-meteo.com and opendata.dwd.de on the Custom domain allowlist
• Git source: FransM-ai/mainframe (GitHub, private repo)

Primary issue: routine hangs with zero transcript activity

Routine: "Bassano Skew-T-briefing" / "Bassano Skew-T-briefing v2"
Trigger IDs: trig_01GtNGtkfnPKqUeAnnUiV8TB (original, now disabled), trig_016oPnCWagtAikmJtJaoTmz2 (recreated fresh to rule out per-trigger corruption — same result)

Failed sessions (all show: infra events complete normally, then last_event_at == created_at forever, no transcript):

| Date | Session ID | Trigger source | Result |
|---|---|---|---|
| 2026-08-21 | cse_01PrrwuvWw627tGKttRU52KU | one-off run_once_at test | stuck |
| 2026-08-22 | cse_01S45pfZ1AEEMn3eKcsRhr2J | one-off run_once_at test | stuck |
| 2026-08-22 | cse_011QwxZYf7kX6t9LRWapUPmV | manual RemoteTrigger run on newly-created recurring trigger | stuck |
| 2026-08-23 | cse_01EyWFit1B2Cq3bRKwvEKaLH | genuine cron fire, 04:50:50 UTC | stuck |
| 2026-08-24 | cse_01J6Muu6WYQNUiHTyzrmfyRS | genuine cron fire, 04:50:37 UTC | stuck |
| 2026-08-25 | cse_01ARAm1P3cHBkANA6CiAW6Aj | genuine cron fire on brand-new trigger v2, 04:50:39 UTC | stuck |

Sample log (identical pattern every time):

env[info]: Allocating sandbox
env[info]: Environment runner started
env[info]: Fetching repository FransM-ai/mainframe (x2)
env[info]: Finished processing sources
env[info]: No setup script configured
env[info]: Starting Claude Code
env[info]: Claude Code process started
[... nothing further, checked hours later ...]

The injected prompt was simply /bassano-briefing (a slash-skill invocation defined in the repo), same pattern used successfully by other routines on this account.

Contrast: other routines on the same account/environment DO work

• "Ochtendbriefing mail" (trig_01K8sW3AB2zEqCJyvk9PHjkt), same custom environment, same git repo, fires daily and produces real transcript activity (multiple minutes of tool calls) and writes/commits files — but has separately shown an intermittent connectivity issue on the same days: api.open-meteo.com calls failing with HTTP_STATUS:000/exit 56, and outlook_send_mail missing from the session's tool list, on 5 consecutive days (2026-08-21 through 2026-08-25).
• "T.C. Zuid agenda-sync" (trig_01PDaWnDgjsoEc76PwNG1SEM) also fires and runs correctly, but outlook_create_event has been absent from the cloud-routine tool list for 5 consecutive daily runs (2026-08-21 through 2026-08-25), despite other Microsoft-365 tools (outlook_calendar_search, outlook_modify_labels, outlook_create_label, etc.) being present.

So: the Bassano routine hangs completely (0% success), while the other two routines run but hit partial/intermittent tool-availability or egress issues. All three problems appeared/worsened in the same ~5-day window (roughly since 2026-08-20/21), which is around when the account was migrated from an ITsmart-org Claude account to this individual micon-it.nl Pro account.

Separately: interactive-session MCP tool-list staleness

In my interactive (non-routine) Claude Code session, claude mcp list reports claude.ai Microsoft 365 as ✓ Connected, but ToolSearch cannot find outlook_send_mail (or any mcp__claude_ai_Microsoft_365__* tool) for 3 consecutive days within the same long-running interactive session, even after the health check reports the server healthy. This may be a related symptom (stale tool registry not refreshing after a connector hiccup) or a separate bug.

What I'd like

1. Confirmation of whether this is a known issue with the routine-scheduling infrastructure (stuck sessions with zero transcript activity).
2. Any guidance on why a brand-new trigger would reproduce the exact same hang as the original one (rules out trigger-specific corruption in my mind, but maybe there's something about my account/environment config that's the common factor).
3. Whether the outlook_send_mail/outlook_create_event tool-list gaps and the api.open-meteo.com egress flakiness are related to the same root cause or separate issues worth filing separately.

Happy to provide more session IDs, timestamps, or account details as needed.