raglencross wrote: 
> 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.

If you're happy doing it this way with a wait after boot then you can
automate that using cron (sudo crontab -e) and adding a line: 


Code:
--------------------
    @reboot sleep 300 && /usr/bin/python3 /your/path/to/the/file/updater.py
--------------------


If 300 seconds seems too long then reduce accordingly.


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