Purpose This study compared prisoners’ and their (ex‐)partners’ forecasts and actual experiences of life after prison. The aims were to: (1) assess prisoners’ self‐expectancies of problems and actual resettlement experiences; (2) compare prisoners’ post‐release expectations and experiences to their partners’ forecasts and valuations of these outcomes; (3) examine whether pre‐prison factors have an effect on each partners’ outlook of the future; (4) examine the predictive utility of each partners’ expectations on the men's post‐release outcomes; and (5) explore a range of resettlement issues which may play a vital role in pathways for reducing reoffending (i.e., family relationships, accommodation, finances, employment, alcohol use, and drug use). Method We employed a prospective longitudinal design and used semi‐structured interviews to gather quantitative and qualitative data from 39 male prisoners in England and their respective (ex‐)partners. Results The couples showed relatively strong agreement on the men's post‐release difficulties compared to their earlier predictions; however, there was some variation in the ‘realism’ and ‘optimism’ of their outlooks. Their expectations were partially based on pre‐prison factors: higher frequencies of pre‐prison problems were positively associated with anticipated difficulties post‐release. Pre‐release expectations significantly predicted the men's post‐release difficulties with substance use and relationship factors. Conclusion Overall, our findings lend support to a dual hypothesis on the function of prisoners’ cognitions of future resettlement. On one hand, a ‘realistic view’ is important in recognizing when one is at risk for adversity. On the other hand, a ‘positive mindset’ has been associated with active coping and positive outcomes (e.g., desistance). The findings also underscore the importance of a holistic, family perspective in release and resettlement planning, and highlight key areas for targeted service delivery to promote successful desistance.