Through qualitative exploration with soon-to-be-released men in three prisons in England, this paper examines the difficulties that prisoners envisage on returning back to community settings; entering other settings such as workplaces; and the implications the transition may have for their health. Interviews and focus groups were conducted with thirty-six prisoners, some of whom were convicted of sexual offences and based on a vulnerable prisoner unit (VPU). While not all prisoners offered the information, approximately two-thirds of the sample had offended previously. The transition that individuals make from the prison setting to the community can be potentially complex and often detrimental to health. Accommodation issues were forecast as a major concern for those men without family ties.Temporarily residing with friends or living in hostel residences were viable options for many prisoners, but both had drawbacks which could increase the probability of engaging in substance misuse. Resettlement issues were perceived to be more difficult for sex-offenders; their 'identity' provided an additional burden which created further re-integration difficulties.Employment opportunities, for example, were predicted to be drastically reduced as the men had signed the sex-offenders' register. The paper suggests that opportunities for successful transition could be enhanced by a more 'joined-up' settings perspective and proposes that a settings-based approach to health promotion, which emphasises the synergy between social settings and addressing wider determinants of health, should be applied to prisons to reduce, rather than exacerbate, inequalities.