Honesty is the best policy. Get it off your chest and whatever the outcome you'll still feel better. Management might even appreciate your honesty.
With regard to uploading I had a PDA the other day that would not send anything. The count went up eventually to 18 including 4 specials. I reconnected comms at least twice logged on and logged off twice before I tried to log off again back at the office. Still wouldn't send. Said it was but wouldn't. Told guy in locker. Went home. Next day got pulled up by manager in charge of complaints/failures etc as if it was my fault! He did go away when I told him what had happened but it was still a bit irritating - as if there is anything you can do to leave a load of stuff on there even if you wanted to!
Next day there were unsent items on loads of them as people came back, must have been something wrong with the main system however that happens.
If I were you and was as worried about as you seem I would ask if it did come up as a failure by way of wanting to learn more about the way it works. Either that or just completely ignore it, if no-one has said anything so far they probably never will!!!