The study is focused on the reentry/resettlement problems that are faced by ex-prisoners in the Czech Republic (CR). Findings are based on semi-structured interviews with 26 ex-prisoners and 30 social workers who provide social services in prisons and after the release. Based on the data, which were coded inductively employing qualitative content analysis, several post-prison issues emerged: (1) material deprivation and insecurity regarding housing, subsistence, and stable employment; (2) debts and enforcement proceedings; (3) prisonisation effect; (4) health issues; (5) relationships with family and significant others; (6) drug abuse; (7) meaningful leisure time. Particularly, more attention was given to housing, subsistence, stable employment, and debts and enforcement proceedings because, compared to other countries, these issues have their specifics in the CR. Findings, interpreted through the optics of intersectionality, suggest that the Czech social policies regarding ex-prisoners are focused on a one or selection of factors, instead on the complex interplay of them, as well as not properly targeted and delivered in the right time. To improve the situation, the better system of social services financing that would address the ex-prisoners’ complex needs must be implemented along with the housing first policy and more accessible personal bankruptcy.