Policy installing cached package installs then states "Failed"

Does your first policy that caches the installer package include an inventory collection at the end? That part is crucial. By default, policies don't run a recon at their completion. You need to enable the Maintenance payload to have that happen.

I don't know for certain if that's the main issue here, but to be sure you aren't getting policies re-running unnecessarily, I would double check that in your caching policy.

My caching policy did not have inventory update enabled. I actually had it enabled on the installer. The package has been on a lot of machines for weeks though and an inventory update has been done since then. Would it still have to be on the base policy?

No, not if you're sure that inventory collection has taken place since it was first cached. If that's the case, then it's not likely that it's an inventory problem you're seeing here.

I can't say I know for sure what it could be. If you're able to post any more details on your policies, such as scripts being used or screenshots of the settings, it might help someone here hone in on exactly what's causing your problem.

I kept it as simple as possible. I didn't use scripts. I just packaged the Catalina update from Mac. and cached it to machines. I then created a cache installer using the command listed above in the installer policy.

I can try and post screenshots shortly of the boxes I have checked.

@Tjernigan This is a bit old, but I'm experiencing this exact same issue. Did you find the cause/solution in your case?

@cfrank12 I did not. Though I have discovered a better way to upgrade my machines using the jamf framework.