What prevents employees from supporting their colleagues who are stigmatized because of their social identity? I develop a theoretical framework based on risk-taking, legitimacy, and trust that explains the mechanisms leading to a stronger relationship between stigmatized employees and their allies along with the factors preventing someone from acting as an ally. Using theory of planned behavior, I theorize and investigate ally risk beliefs shaping ally risk-taking and propose how servant leadership can reduce the impact of these risk beliefs on risk-taking. My dissertation findings contribute to HR theory and practice by advancing research on allies to employees with a stigmatized identity and opens avenues for further discussion on the relationship dynamics between stigmatized employees and their allies which may thrive under the supervision of servant leaders.