I need to do a confluence upgrade from v5.0 to v5.4 and a migration from a windows desktop using oracle to a linux virtual server using MySql. We also use the EAR-WARS edition which adds some complexity. There are also some in house plugins which broke and needed to be fixed on our last upgrade so I am suspecting the same problem this time around. Does anyone have any advice on the order we should perfrom these steps? do you upgrade first on windows and then migrate? or migrate to linux and MySql and then do the upgrade? should I fix the plugins after the upgrade on windows and prior to migration or just wait till the end to start fixing the problems? I have read through the different migration documentation but I am still unsure really where to start and which step I should be doing first.
You should do this in a test environment first. Backup your db and Confluence App and restore them to another machine. Atlassian has a document for migrating to another machine. I'll put the link below. As for which to do first upgrade or migrate I don't think it matters much but test the process and follow the same order when you do prod.
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