Women fill the majority of the entry and midlevel student affairs positions across institution types yet are underrepresented in senior-level roles such as the chief student affairs officer role at doctoral-granting institutions. This explanatory mixed-methods study explored the experiences and perceptions of midlevel women student affairs professionals at doctoral-granting institutions. Of specific interest is how these individuals have experienced the culture and climate of their institution and how they perceive they have affected their career aspirations. Two-hundred fifty-seven participants completed the online survey and 10 completed a 60-minute semi-structured interview. Findings from this study revealed that women midlevel student affairs professionals continue to face challenges due to the cultures and climates of their institutions, which affect their career aspirations. Although about a third of the participants indicated that they aspired to senior leadership roles, personal and professional factors that are not supported by institutional cultures and climates have derailed their career aspirations.