updating OSX in 2019 27" iMac

[macj3]

I have a 2019 27" iMac, 3.7 i5, 8Gb ram, 1tB SSD. Running Mac OSX 10.14.6. The new Tax program needs 10.15. I was wondering If I should just "jump up" one OS from 10.14 to 10.15 or go further? Maybe all the way to macOS Monterey? Will the newest macOS Monterey play well with my 2019 iMac? or just go to Catalina (10.15) or Big Sir (11.6.2)? Would it be best to jump incrementally or just go up in one big leap?
Have an iPad running iOS 12.4.9, will that be effected?
Thanks in advance for any replies!

 

[Cayenne1]

I have a 2017 iMac 27" 1TB SSD and went from High Sierra to Monterey. It has worked very well but note I did a PC type clean install. That is I totally wiped the system disk and reloaded and re-configured each account, application and data by hand one by one. NO Migration assistant.

This approach takes time to prepare and execute. I maintain approx. 60 application installers on a separate HD including Windows apps via Parallels. Included with the installer folders are any application account logins and license key information. Prior to upgrade, I note any key settings including all System Preferences by taking screen snapshots prior to wiping the disk. I do not rely on copies of pList files.

Think of it as I just got a new Monterey Mac in a box, Migration Assistant doesn't exist and I want to load all my current Mac programs, data and accounts onto it. How would you do that without losing anything but Customization settings.

There is a downside to Monterey and I think Big Sur as well. You can no longer create reliable bootable Carbon Copy Cloner image backups per CCC documentation. I used CCC to restore HS in the past, But now its messy. If I had to restore a blown Monterey disk I'd use my approach above combined with Time Machine data recovery as necessary.

Sorry, a lot of explanation, but going to Monterey should work fine. Just make sure to do prep for the inevitable "oops".

 

[Fishrrman]

Before you upgrade, be sure that you have no other software that requires a 32 bit OS. Mojave (10.14.6) is the last OS that can run 32 bit software.

Another way to do things:
Get a small USB3 SSD (256gb would do fine, you can put one together yourself easily).
Install Monterey onto it (easy to do).
Install your tax software onto this SSD.

Now you can boot from the EXTERNAL SSD when you need Monterey, and your internal setup is left "untouched".

You can also "experiment" with all your other applications, so you know they will continue to work -- BEFORE you upgrade. Once you upgrade, "getting back to where you once belonged" isn't so easy, so... look before you leap.

 

[BrianBaughn]

What I'd do is use Carbon Copy Cloner (it's free for 30 days if you've never used it before) to clone the Mojave installation to an external drive. The external wouldn't have to be an SSD.

Then, you can try the Mojave to Monterey installation on your internal SSD…knowing that thing go badly you have the clone as a backup. If the upgrade to Monterey goes badly (either a failure or software doesn't work properly) you can then try a clean install of Monterey on your internal and immediately use Migration Assistant to migrate from the clone.

If upgrading AND migrating both fail you still have your Mojave clone and can try other methods.

Be sure to read Apple support documents regarding upgrading your system.

 

[macj3]

Thanks to everyone who replied. I guess I'l get an SSD external, clone the system to it and then upgrade that ...need to do alot of prep and reading before I go further. I don't have any 32bit programs. so that's one thing not to cause issues....Thanks again.