Issue Description

We've had a few customers raise various Ruby-related issues with Crons, such as missed check-ins, failed check-ins, etc when they're not suppose to be failing.

Reproduction Steps

Monitor details can be found here: https://sentry-crons-05.sentry.io/issues/alerts/rules/crons/ruby/ruby-whenever-upsert/details/?end=2025-07-24T22%3A18%3A00&start=2025-07-24T21%3A44%3A00
Code: https://github.com/getsentry/sentry-crons-examples/tree/main/ruby/whenever

See additional details in the linked Linear issue.

Expected Behavior

Check-ins should never fail or be missed.

Actual Behavior

Check-ins are intermittently failing/not being sent to Sentry

Ruby Version

3.2

SDK Version

5.26.0

Integration and Its Version

No response

Sentry Config

No response