I have tried running "ExecStartPost=/bin/sleep 90" before the updater script with no success. Interestingly, if I increase the sleep time to anything beyond 90s (e.g. 2m), the ngrok web gui is not accessible. I understand your "EDIT", but is it possible there is some interaction between the "sleep" and the "Restartsec" times that results in the behavior I am seeing? Regardless, I am still able to get things working by manually running the updater script several minutes after rebooting. Not as elegant as having the updater do its thing, but certainly faster than using the Alexa app.
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