In addition to standard parole conditions, parolees under federal community supervision may be subject to special conditions as determined by the Parole Board of Canada; such conditions are intended to manage factors associated with criminogenic risk and need. One set of special conditions places restrictions on parolees’ social relationships and associations, which can include general restrictions (e.g., non-association with individuals involved in crime) or specific restrictions (e.g., no contact with one’s victim or co-accused). Drawing on case files of women under community supervision (n = 43), we explore how non-association and no contact orders shape community release experiences. We suggest that such conditions can have wide-reaching effects on women’s social lives and reintegration (e.g., in the areas of social support, employment, and housing), thereby, at times, complicating women’s attempts to construct post-institutional lives and identities. We consider how association conditions illustrate the broader tension between parole requirements and reintegration.