Timeout check-ins do not create issues under some cases

[rodolfoBee]

Environment

SaaS (https://sentry.io/)

Steps to Reproduce

1. Create an interval cron monitor that expects a check-in every 5min
2. Set the timeout time to any value longer than 5min, for example, 10min.
3. Send only "in progress" check-ins every 5min

Expected Result

When the check-ins start to timeout after 10min, an issue is raised in Sentry.

Actual Result

The consecutive "in progress" check-ins seem to be preventing the timeout issue from being raised. Screenshots from two affected organisations.

Normal timeouts (with no check-in afterwards) raise issues as expected.

When check-ins are still in-progress:

Multiple timeouts:

Internal issue link
Similar to this issue: #59431

• link to test monitor: https://dev-curumas.sentry.io/issues/alerts/rules/crons/plain-python/ef57c573-124d-497e-bae7-7e2bfa057da9/details/

Product Area

Crons

Link

No response

DSN

No response

Version

No response

[getsantry]

Assigning to @getsentry/support for routing ⏲️

[getsantry]

Routing to @getsentry/product-owners-crons for triage ⏲️

[evanpurkhiser]

@gaprl We're tracking this in Linear now yees?