Someone who can't function being out of jail
Solution 1:
The term institutionalized is often used
(Of a person, especially a long-term patient or prisoner) made apathetic and dependent after a long period in an institution.
Oxford Dictionaries Online
Note that the term is used for people who have been in other types of institutions, such as mental hospitals.
Solution 2:
In the movie Shawshank Redemption, Red tells Andy that Brooks has been in Shawshank for so long he was "institutionalized."
http://youtu.be/Fl3J_QDBRMs