This has been the case for about the last 10 Releases and perhaps even longer. Our scenario is that we have some environments with passive (push) tentacles and some with active (poll) tentacles. All tentacles are running as an AD service account that is local admin on each server.
When a new Release of Octopus comes out, of course we go ahead and have Octopus upgrade the tentacles for us. In the case of the Active tentacles, about 90% of the time, it just hands on the upgrade and you need to click Cancel. If you then go in and do a health check on the machine or whole environment, usually you will see that the upgrade did, in fact, occur. This is what we see in the UI when it hangs:
This server does not have version 3.1.30 of the Calamari package. It will be pushed automatically.
C:\Octopus\Calamari\3.1.30\Success.txt
Running Tentacle version 3.2.16
Beginning upgrade
Waiting for Tentacle to shut down and restart with the new version 3.2.20…
Running Tentacle version 3.2.16
Because Octopus will only do 8 or so machines at a time, this can become very tedious.
It should be noted that this does happen about 10% of the time for Passive tentacles as well. Can anyone help?