Abstract: The comparative rate of women entering the formal correctional system and serving custodial sentences, both in prison and prison remand awaiting trial, is on the increase. This is accompanied by a similarly increasing number of women eventually exiting prisons annually. This study sought to investigate the Relationship challenges influencing re-integration of women ex-offenders in Nyeri County, Kenya. Labeling and the social bond theories provided the theoretical framework. Case study design was used. With the site selection and sampling procedure being purposive, respondents were picked through snowballing until saturation was attained with a sample size of 41 women ex-convicts. The Key informants and Focused group discussants were also purposively selected. Data was collected by use of semi-structured interview schedule orally administered through personal face-to-face interviews and field sheets. The results showed that change in relationships between the ex-convicts, their families and significant members in the community were the major issues that the ex-convicts faced. Some indicated that they had good relationships while others had strained relationships, both before and during incarceration or even after release. Research on methods to smoothen the relationships between female convicts and their families and the communities they are released into is recommended in order to ameliorate the process of reentry and re-integration. Understanding relationships’ related challenges is significant in successfully re-integrating back into the community for the women returnees in the Kenyan context. Key words: Relationships, offenders, ex-convicts, incarceration, re-integration