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I need to update my OS from 10.9.5 to the latest OS (on a macbook pro). Can you tell me if I can do this in one go, a single update? Or is it a two-stage job, updating to a newer OS and then from there to the least OS? I've had different answers from the apple staff I've asked. Ta for any tips.
That’s a big jump.
But Apple says you can go direct
“Most Mac models introduced in 2012 or later are compatible with macOS Mojave, and you can upgrade directly from OS X Mountain Lion or later.”
https://support.apple.com/macos/mojave
And make sure you do a time machine backup before you start!!!!
A cleaner option might be a fresh install and then copy what you need over from a backup.
Do two backups on separate discs, plus the time machine one. If you want to be thorough a minimum three pass erase before a fresh install will make things sparkly. (The erase can take a day to complete depending on disc capacity and hardware speed).