Prisoner made to pay penalty in prison? (8)
I believe the answer is:
confined
'prisoner made to pay' is the definition.
I can't judge whether this defines the answer.
'penalty in prison?' is the wordplay.
'penalty' becomes 'fine' (a financial penalty).
'in' is an insertion indicator.
'prison?' becomes 'cond' (I can't justify this - if you can you should believe this answer much more).
'fine' put into 'cond' is 'CONFINED'.
Can you help me to learn more?
(Other definitions for confined that I've seen before include "put inside" , "Lacking freedom" , "locked up" , "Restricted" , "deprived of freedom" .)