I recently had to upgrade a couple of servers running 10.8.5 to High Sierra. And found that it had to be done in stages- you can only go up 2 version of operating system at a time- try 3 and you’re SOL. but 10.8 to 10.13 is 5 versions of upgrade? So how did we do it?


  1. Backup, Upgrade to Yosemite 10.10.5, then log in to App Store. Click ‘install’ for Server. It will ask if you want to download an older compatible version, say yes. Install, test. Backup
  2. Upgrade to Sierra 10.12.6. Install Server.app v5 and test. Backup
  3. Upgrade to High Sierra, upgrade Server.app. Move shares, test, backup.

Get a pint of vodka. Neck in one gulp

This job took about 500% longer than I’d quoted, but in fairness I did do a lot of testing so I could be prepared if this happened again. Let’s hope it doesn’t!


On other interesting thing about this upgrade is that you can’t share folders from an APFS volume properly. When your client is a non High Sierra machine, you can browse to the first level of files, but you always get permission errors when trying to browse down more levels. The solution is to move the shared folders to a non APFS volume and share from there, which does operate as expected.