It seems when upgrading every so often a tentacle will just keep sending back the old version number when upgrading and then never upgrade. The only solution to this is to cancel the upgrade then start it over and this usually fixes it. This usually happens to at least a few of our tentacles every upgrade. Would it be possible to build in something where if it reports the same version number over and over it restarts the process on that tentacle? Attached is screen shot.
Thanks for getting in touch. We updated the tentacle upgrade process (https://github.com/OctopusDeploy/Issues/issues/2145) late last year to wait for 15 minutes to prevent polling tentacles from hanging. Do you know if it completes within this timeframe or do you cancel it before it times out? Does it fail different tentacles each time or is there any pattern you can see?
Looking forward to your reply.