I held back on El Capitan for a while as generally you don’t want to be on the bleeding edge in production but as macOS Sierra is around the corner, it’s time to get everything tested on El Cap.
Of course back up everything first.
I’d already upgraded VMware Fusion to version 8 at this point which is important as version 7 doesn’t have El Cap support. So with that prerequisite out of the way I merrily get on with the upgrade.
Downloading from the Mac App Store is painless as can be expected with he only weirdness of the double Agree dialog but whatever.
While I tested the upgrade process directly on the console, you can actually do this upgrade remotely over Apple Screen Sharing or other remote solutions like Remotix. (Of course there are risks involved, make sure you budget extra time and be ready to jump in your car if all goes tits up.)
Having said that, it’s at this point I ran into a minor obstacle while upgrading the production server. Apple Screen Sharing services won’t start until you’ve clicked through the initial setup wizard. Which is fine and dandy when you’re on the console but at a remotely, it’s a catch 22. You need Screen Sharing so you can click through the wizard but Screen Sharing won’t start until you’ve clicked through it.
So another lesson here is to have a robust remote access setup, and don’t rely on any single method. Thankfully I had two other methods on which I could fall back on. Goto Assist didn’t work either (it must be that all services don’t start until this cursed wizard is defeated) so I logged on to the remote kvm (which doesn’t rely on the OS) and finally vanquished this Gandalf-like wizard. Of course, there was always the car.
So there you have it. 3 lessons learned.
- Backup first.
- Check your software prerequisites before upgrading.
- Strange wizards can pop up and ruin your afternoon so be ready to defeat them with a robust remote access solution.
The Infosec Noob 