How do I upgrade to the latest OS Catalina if I'm currently on OS X Yosemite 10.10.5
I have a MacBook Pro 15in Retina, Mid 2014. I'm on OS X Yosemite. Can I upgrade to OS Catalina? And if now, how high can I upgrade?
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You can upgrade to the current macOS Catalina 10.15.7. See information in How to upgrade to macOS Catalina - Apple Support