PMP Packages are Deploying but not Installing

[CODRyan]

I apologize for the probably "newb-level" question here, but I am hoping for direction on where to start with troubleshooting an issue I'm seeing on many devices in our environment (Configuration Manager). 

Example of the behavior I'm seeing: A device shows in Advanced Insights that several updates are required, spanning back quite some time.  This is a device that is otherwise receiving and applying non-PMP applications/packages as well as Windows/Office updates via ADR's in Configuration Manager.

If I log into this device and browse to C:\Windows\ccmcache, I can find the packages corresponding to the required updates but they're seemingly never being installed by the SCCM client.  I've tried manually running Machine Policy Retrieval/Software Updates Deployment Evaluation/Scan cycles, but those particular packages seem to never kick off.  Meanwhile, the majority of machines in those same collections are working as intended.

If I could get some help on where to look for breadcrumbs that would be greatly appreciated!

[Michael (Patch My PC)]

Hey CODRyan,

If you are seeing the contacted in ccmcache, but the updates are never installing, you might want to check the 'deployment' schedule of the Software Update Group that the updates are apart of.

If you don't have a maintenance window configured for the device, and the 'deadline' time for the deployment is in the future, then the device is waiting for that deadline time to run the updates.

You could also be in a situation that the deployment is perpetually getting extended to the future depending on how your ADR is configured.

I would suggest submitting a support case, or schedule a Review session and we can go over your setting and maybe see what is going on.