The article explores desistance dynamics within prison, and what gang members say about its phenomenology. Qualitative methodology was adopted with research participants in English and Scottish prisons. The findings indicate desistance oriented dispositions develop gradually once gang ties, originating in the street gang, lose the resonance they once exercised on conformity to offending behaviour. This liberation from oppression means not merely that gang members are de facto left to fend for themselves, but also to find a liminal space in which to thrive. It gives them an opportunity to learn and develop pro-social values. Spirituality, a source of personal meaning, supports progression to desistance and fosters distance from the street self. Gang members’ loyalties and conflicts pre-dating incarceration challenge the potential of prison to break criminogenic ties and foster desistance.