Upgrading from Mavericks to Sierra?

[splitpea]

Yeah, this machine is way behind the times. There have been some misfeatures and bugs in newer versions (encountered on work computers) that I've tried to avoid by staying on Mavericks, but it's finally gotten to the point where I can't install some software/upgrades due to the older OS version.

Could someone please help out by answering a few questions that are still holding me back from starting the upgrade process?

1) If I take a bootable backup using SuperDuper before the upgrade, I can restore from that and go back to Mavericks in a pinch, right?

2) Will my non-subscription versions of Photoshop (CS6) and MS Office (2008) still run properly?

3) Should I do a completely fresh install and migrate, or an upgrade? (Keeping in mind I have a ton of data and config that I don't really want to have to restore after the fact; but would also like to get a clean system.)

4) Is there anything else I should be asking or keeping in mind regarding this upgrade?

Thanks for your help!

 

[Fishrrman]

"If I take a bootable backup using SuperDuper before the upgrade, I can restore from that and go back to Mavericks in a pinch, right?"

Yes. BE SURE to do this.
I've seen many many posts here from others who upgraded without a cloned backup, and then started asking, "how do I get back?" afterwards (when they were unhappy).

I suggest El Capitan instead of Sierra.
Because it represents a "mature" version of the OS, as distinguished from Sierra, which is still in something of an "early release version".
But that's just me...

 

[CoastalOR]

1) If I take a bootable backup using SuperDuper before the upgrade, I can restore from that and go back to Mavericks in a pinch, right?

2) Will my non-subscription versions of Photoshop (CS6) and MS Office (2008) still run properly?

3) Should I do a completely fresh install and migrate, or an upgrade? (Keeping in mind I have a ton of data and config that I don't really want to have to restore after the fact; but would also like to get a clean system.)

1) A caution on SuperDuper!, it does not clone the Recovery partition. If you have to restore 10.9.5 from the SuperDuper! clone then your internal drive will not have the 10.9.5 Recovery partition, it will have the 10.12 Recovery partition. Carbon Copy Cloner (CCC) can clone and restore the Recovery partition. CCC has a fully functional 30 day trial. I have used it for years and it has never failed me.

2) They should work ok as long they are still on the original Mac that they were installed on. Another reason not to do a fresh (clean) install. People have been successfully using Photoshop (CS6) and MS Office (2008) with Sierra.

3) I have had good luck with the upgrade method. If you have issues then try the more extreme methods. BTW, before upgrading, test you clone backup by booting from it.

 

[chown33]

The answers to #1 and #2 can be confirmed by actually booting from the cloned backup. You should do this, so you know what actually happens, rather than relying on someone's description of what ought to happen.

I would answer #4 by saying, "Always test a bootable backup by booting from it." Which relates to #1 and #2.