Contrite worker who’s been confined again? (9)
I believe the answer is:
repentant
'contrite' is the definition.
(similar in meaning)
I can't explain the rest of the clue.
(Other definitions for repentant that I've seen before include "Contrite" , "Regretful" , "Feeling remorse for misdeeds" , "showing contrition" , "sorry state" .)