Years ago, I once got hassled for entering a checkpoint repeatedly in DTW when I was trying to deal with an IROPS hotel issue (an agent inside security was helping me out, and I was trying to check in to the Westin hotel outside security). The agent rejected my existing boarding pass for being previously scribbled on, and the new boarding pass was for the next morning so invalid for entry.

I really enjoyed the look on the officer's face 10 minutes later when I returned with a gate pass produced by a DL checkin agent, with justification entered as "TO GET PAST TSA AGENT".