I think there’s a way to do this. Here’s my hypothetical setup:

Let’s say you want to send your checklist on Jun 1 and close on Jun 14. Make the work start date Jun 14 and schedule your client request to go on Jun 1. You’ll be sending the client requests when the work is in ‘Planned’ status.

Add the two automations I show in my screenshot so that when Jun 14th passes, the work goes from ‘Planned’ to ‘Ready to Start’ triggering the first automation, which triggers the second automation, marking the work ‘Completed’.

I was just looking at this as well. @max In this case would the client tasks remain open even though the work is closed? I was looking for a way to mark the client tasks as completed, it came up in another conversation in the Community and I could not see a way to make it work.