I’ve been having a consistent, problem with a tentacle on a Win 10 server.
Consistently it fails to restart the tentacle when the machine restarts. The service is marked as automatic so it should restart automatically, but its not. Since I was a version behind I went and updated the server. All the tentacles updated, except my Win 10 server.
So i installed the tentacle manually and I can see the service running, but the tentacle app itself keeps returning me to the welcome screen and I can add the service again.
I then uninstalled and reinstalled the tentacle and that had the same effect.
For the original issue we have our watchdog service which will catch the Octopus service didn't start issue that you experienced. Have a read of the page I linked to as to why we went with this approach.
As for your current issue, are you able to let me know what state you’re in? A screenshot of the screen your presented will probably go a long way. The only suggestion I really have at this point is to do a full manual uninstall of Tentacle, then re-run the installer and see if you run into the same problem.
It may also be useful to attach any logs (c:\Octopus\Logs) for this Tentacle, provided we have gotten to the point of writing logs that is.
Hopefully we can get this sorted for you, I look forward to hearing from you shortly.