I created a task to run on a Server 2016 DC, with three triggers: at system startup without delay, a second one at system startup with one minute delay in the trigger's "advanced settings", and and a final time at startup with 2 minutes delay.
The task was executed after a reboot according to the task history, but apparently the delays are being ignored.
I got two warnings "Launch request ignored, instance already running".
Besides that, the first few logs are missing from the history, maybe because the system wasn't ready to log them yet so close after a reboot (it happens to be another issue like that that I was trying to circumvent by retrying twice).
The entry at 10:15 in the screenshot is from a test run before rebooting.