Hi everyone, I just stumbled across a surprising behavior with combined SCHEDULED and DEADLINE timestamps that repeat. Here is the example org file contents:

* TODO My late recurring todo

SCHEDULED: <2023-04-12 Wed ++1w> DEADLINE: <2023-04-13 Thu ++1w>

Right now it is Wednesday (2023-04-26 to be precise), and as shown above, my task had a scheduled timestamp on a Wednesday from a previous week. The repeater is ++1w, so marking the task as done bumps it to repeat on Wednesday of next week (2023-05-03 to be precise). That functions as expected.

But the deadline timestamp is on a Thursday of a previous week with a repeater of ++1w, so marking the task as done bumps it to Thursday of this week (2023-04-27 to be precise). So marking it as done it has the logical but unexpected result of having the scheduled timestamp for a date (2023-05-03) after the deadline timestamp (2023-04-27).

Is there a way to link the timestamps so that marking the task done will always bump the deadline timestamp after the scheduled timestamp? On the IRC channel I was kindly directed to look into org-todo-repeat-hook as a way to approach it, but to share this here in the mailing list as an edge case to be considered.