Can I upgrade to macOS Monterey from High Sierra

joannefromtampa Said:

"Can I upgrade to macOS Monterey directly from High Sierra??"

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Verifying Compatibility:

A. Start Here: Learn About Compatibility and how to Identify your Specific Mac Model - Apple Support

B. How to Verify:

I. Reveal your Model:

What is the Model of your Mac? To find out...

1. Go to: Apple menu
2. Click: About this Mac
3. View: Second Line-Down

then...

II. Compare the Results:

See if the Model you found is shown here: macOS Monterey is Compatible with these Computers - Apple Support

III. If Compatible:

Back Up your Mac First:  Be certain you Create a Time Machine Backup of your Mac, so that way you can have something to restore your Mac from, should anything go wrong with the reconfiguration.

The Age of this computer will Govern what newer version of macOS it will Qualify to install. Use About this Mac from the Apple Icon on Desktop - the required Information will be there.

With the above information in-hand - follow this How to get old versions of macOS and verify what version this computer Qualifies to install.  For Best results use Safari to commence the download as Others may not work.

Safari will open a redirect and open the Apple Store where the download can commence.

Computer Qualify for the Monterey upgrade

macOS Big Sur 11 hardware requirements

macOS Catalina 10.15 hardware requirements

macOS Mojave 10.14 hardware requirements

Caution - jumping over all the newer versions and directly to Big Sur  / Monterey on Qualifying computers is Technically possible - there are those who have attempted and were successful. Then there are those who attempted and had less than good results.

If this is a Production or Mission Critical Set-up - a more prudent and measure approach is suggested. 

The above is from observations on the Apple Support Community Forums and IMHO

Tips Big Sir Upgrade Released Nov 2020

Tips Monterey Upgrade  Released Oct 25, 2021

Make Time Machine Backup  is very useful and can be used to Revert to Previous Working macOS

Notation - Mojave is the Last version to support 32 bit applications / extensions and Drivers. Catalina, Big Sur & Monterey supports only 64 bit and there is no workaround.

Suggest using Go64 to find 32 bit application before attempting the upGrade. Some or many of the Application already installed may required update or upGrades to 64 Bit Versions.

Tips Monterey Upgrade 

SSD Drive or Fusion Drive or worse still Rotational / Mechanical Drive ?

SSD would be Best and anything else - well be sure to a Rescue Plan

Do you have a Rescue Plan In-Place. This comprises having 3 Backups using 2 methods and 1 Off Site incase of Theft, Loss or Natural Disasters. A Time Machine Backup  is very useful and can be used to Revert to Previous Working macOS. 

For addition purposes - two Tested Bootable Clones each to separate external drives. This is insurance incase the upgrades goes sideways. At least one Tested Clone and / or Time Machine Backup should be Off - Site

Yes, if your Mac's compatible.

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joannefromtampa wrote:

can I skip the intervening updates and go directly to Monterrey?

Yes.