Upgrading from Mavericks to Sierra: What to look out for?

[danqi]

My 2014 MacBook Pro and my 2010 Mac Pro are both still running OSX 10.9.5, mostly because of some specific software compatibility issues and because I use these machines for work and am always hesitant to upgrade.

Now, the time has come where the compatibility issues of not updating have gotten bigger than those of updating and I have decided to take the plunge and update both Macs to Sierra.

Is there anything I should be looking out for to make this go smoothly? Anything to prepare before I update and any (hidden) settings or issues I should address afterwards?

To be honest, I have been out of the loop for such a long time that updating seems a bit intimidating...

 

[Rok73]

Make a backup and update.

 

[throAU]

^ whs.

I'd make a backup and try an upgrade, but be prepared to wipe clean and restore data if it doesn't go well.

Reinstalling OS X from scratch isn't that scary so long as you have a decent backup. I'd make 2 backups, just to be sure (just in case you find your backup is not as healthy as you thought).

 

[Fishrrman]

Posts 2 and 3 have it right.

The most important thing you can do BEFORE you attempt the upgrade is -- create a BOOTABLE CLONED BACKUP using either CarbonCopyCloner or SuperDuper.
Both are free to download and use for 30 days.

If you DON'T have a bootable cloned backup, you will find it VERY challenging to "get back, get back, get back to where you once belonged" if for some reason the upgrade doesn't go well.

With a cloned backup, you can just:
1. boot from the backup
2. re-initialize the internal
3. RE-clone from the cloned backup
... and you'll be right back where you started from.

Otherwise.... ?????