@rlkoshak I have found my root of issue, described by lots of others here.
Basically cron is really unrealiable, so that’s why my Time Of Day won’t get updated every time (when it should get triggered by a cron).
Here is my original issue: Cron job failing to execute on OH 2.4
Is there a solution to drop cron triggers? Or how this ‘problem’ could be solved?