For now several years, many researchers have emphasized the importance and effectiveness of parole in the reintegration process of offenders, especially in reducing recidivism rates. A review of the existing literature revealed that, although little was known about conditional release decision-making in general, there was a flagrant lack of scientific knowledge pertaining to conditional release decisions regarding women offenders incarcerated in Canada. Using a constructionist theoretical framework and qualitative thematic analysis, this research aimed to understand which “factors” were documented by the Parole Board of Canada’s (PBC) Board members in their written parole decisions for federally incarcerated women in Canada who were serving a sentence of five years or more, between 2005 and 2015. The findings ultimately showed that, despite the implementation of more stringent government policies based on risk management, the PBC’s Board members seem to have retained their concern of promoting the reintegration of women offenders in their parole decisions. The analysis revealed that the Board members have indeed continued to place great emphasis on the women’s potential for change through a discretionary assessment of their dynamic factors. This seemingly more reintegrative vision nevertheless remains marked by the risk management approach, which raises questions about the way Board members interpret and evaluate the specific needs of the women and their potential for reintegration.