Seen this too many times before, where the users (Developers were unaware of a server reboot that caused their Tentacle to stop. Here is a defensive way to make sure your Tentacles start consistently.
Here is how to update the Octopus Tentacle in the case that the server is scheduled for downtime or just in general to avoid Tentacles being or considered offline within the Octopus Deploy server UI. Typically during installation of a tentacle on a destination server you don’t have the ability to recover gracefully if something goes wrong. This can be troublesome during patching or long server reboot times. Hmmm. For some automation here.
Open PowerShell as Administrator:
Scroll to OctopusDeploy Tentacle service:
Right click and select properties:
Change Startup type to: Automatic (Delayed Start)
Switch to the Recovery tab:
Change the 1st, 2nd, Subsequent failures to Restart the service
Click apply or OK and you will now have a tentacle service that will be more stable after your machine boots from either a scheduled or maintenance reboot.