I'm a partner at a small software development company. We've got 23 employees and 30ish MacOS machines. I've been searching for a better way to handle OS updates than walking around and making sure all updates are installed. I'd prefer not to turn on auto-updates on all of the machines for a number of reasons.
I tried Apple Remote Desktop, but it seems to have issues when the machines have FileVault on. I have tried sending unix commands to the machines (softwareupdate -i -a) to get them to update. It downloads the updates, but always hangs installing. I can run around and type in passwords to get past FileVault, and if I get to all of them fast enough, they will install...
So...in my research, it seems DEP-enrolled machines is what I need, plus an MDM to force the updates to run. Over the years, we've bought the machines via Apple Retail, with no customer number, so it seems like I'm screwed on DEP. I tried Jamf NOW, but without DEP, I can't push updates.
Is there something I'm missing?? It really seems like there's got to be some way to easily manage a small network without needing to buy all new machines so that they are DEP enrolled. Does anyone know if there's some magic with Remote Desktop I'm missing?
Greatly appreciate any advice. This has been driving me crazy for months now.
