In my setup I have three environments: Dev, Demo and Prod. We have multiple projects and for one weird reason (I don’t want to explain that here) I have to have one machine in two environments. So in Dev and Demo I have machine X. When doing an “Upgrade all” the tentacle upgrade on that machine fails but it works fine on all the other machines. I’ve had that problem the last couple of upgrades now so I think it is caused by the machine beeing in two environments.
Upgrading the tentacle manually works just fine and that is how I do it now.