updating macOS from Monterey to Ventura

[TheCrusher4Real]

First time I've attempted an OS upgrade in Jamf. Trying to upgrade some devices at work from Monterey to Ventura. 

I have a Smart Group to show me how many devices are running Monterey. In Jamf, I went to "Software Updates", found the name of my group and selected the checkbox, then clicked "Update 1 selected".

Then selected “Download, install, and allow deferral” and set “Target version” to the most recent version of Ventura (13.6.8). Set the deferral value to 1. End users have received plenty of notifications by now, but thought I'd try to make the upgrade process as painless as possible for them.

Did this about a week ago. None of the devices installed the new OS. When I query a specific device in Jamf and look in "Management > Management Commands", I see this:

Not sure what I've done wrong. 

[jamf-42]

Scheduled updates require macOS 14. 

For major upgrades, you'll want to look at Nudge https://github.com/macadmins/nudge or https://github.com/grahampugh/erase-install

or you can roll your own with cached installers / smart groups and Swift Dialog. 

Updates via MDM are next to useless and really you need to be on macOS 14.6 anything else is not secure. 

[obi-k]

Can you jump to Sonoma? Try caching and installing from the installer as well.

https://mrmacintosh.com/category/macos-installer/

[TheCrusher4Real]

Good callout. Was going to mention this in the original post but opted not to. With this particular user group, we opted to go to Ventura first and then to Sonoma as a second step. Getting this group to make any changes at all is an ongoing battle and they will freak out if a shade of a color appears to suddenly be in a different shade. It's an ongoing process of user education, but we're getting there sloooooowly.
At any rate, this is why we opted to upgrade to Ventura first.

[jamf-42]

so thats double the work for you and two lots freak out for them... and macOS 15 is just round the corner.. move to Sonoma.. you'll thank yourself later.. even if they won't 😎

[mschlosser]

I agree with the recommendation for https://github.com/grahampugh/erase-install recently used it for 100+ machines, and only had to touch one. Pretty epic. Can upgrade or erase. hope that helps