We have had the same problem ongoing now since we began using the Crio's. Sometimes it will deploy, most often it will not. We have checked with the system manager and it does not show high utilization.
There are two solutions. You can get in the habit of throwing the no-execution switch on the crio so it boots without running the code, or you can reimage it. Either way will allow ou to deploy your code (just remember to change the dip switch back if you go that route).
We've met a number of other teams with the same issue, and I believe if you search you'll find other threads about the same thing.
http://www.chiefdelphi.com/forums/sh...517#post951517