If you flush the failed management commands from the affected device I have found it will try again (I found it happened the next day), there is usually a failed command for the app in question.
You can also batch flush for a group of devices using the "Action" button at the bottom of a list of devices.

I've also found that flushing the "Pending Apps" in the History tab will help with this, but alas there is no action button to do this for multiple devices.

Gabe Shackney
Princeton Public Schools