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Past Due - Will be retried

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I deploy a lot of applications in my environment every year after our computer labs are re-imaged. This year we got a ton of computers that would just get stuck on random apps in Software Center saying "Past Due - Will be retried" - they never retry on their own even after rebooting the computer and waiting days. Clicking the app in software center and clicking install forces it to install but we have to this on every machine which isn't realistic. It just seems to be very unreliable when deploying multiple applications at once - the apps are all fine as they work on many other computers. 

1. Is there a way to force all PC's in a collection to "retry" on it's on via Configuration Manager?

2. Here are my deployment settings - please let me know if there is a better practice of doing this when pushing multiple applications at once. I always set it to "as soon as possible" just so it installs in the background as needed and I just deploy all of the applications to each individual collection at once:

Deployment Settings: Install, Required

Scheduling: Installation deadline - as soon as possible after the available time

I always check "Software installation" for the option of "When the installation deadline is reached, allow the following activities to be performed outside the maintenance window. I also leave the "Commit changes at deadline or during a maintenance window" checked as well. 



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