I have a maintenance window that runs from 10PM to 4AM daily. I have three deployments with deadlines during that time. I'm also using the default restart times of 90 minutes and then 15. One of them runs at 11PM, the next at 1AM, and the last at 3AM. Two are software updates.
So if the first runs at 11PM and the updates install (they had already downloaded prior to the deadline) successfully. They each have a max runtime of 5 minutes. Now a user is still logged in from earlier that day. The 90 minute restart countdown starts.
Will the second deployment still run at 1AM if the first one hasn't completed its restart yet?