While deciding which OS to use for the VM, I ended up with CentOS, as that’s the only one on which the installer is officially supported. Fixing that requires some fun directly in the database, but that’s a story for another day (it’s also well documented on the Atlassian support page.) Setting the stage In my case the biggest pain point was authentication, I’m using the JIRA user database for Confluence, and when restoring from backup, your application link from Confluence to JIRA won’t get restored, so the first thing you do is you lock yourself out of Confluence. Backing up JIRA and Confluence is always a bit of a pain, especially if you want to move across servers. I used to run JIRA & Confluence “bare metal” on an Ubuntu machine, but recently I’ve decided to put them into a VM.