As people living with HIV/AIDS (PHAs) achieve more stable health, many have taken on active peer support and professional roles within AIDS service organizations. Although the increased engagement has been associated with many improved health outcomes, emerging program and research evidence have identified new challenges associated with such transition. This paper reports on the results of a qualitative interpretive study that explored the effect of this role transition on PHA service providers' access to mental health support and self care. A total of 27 PHA service providers of diverse ethno-racial backgrounds took part in the study. Results show that while role transition often improves access to financial and health-care benefits, it also leads to new stress from workload demands, emotional triggers from client's narratives, feeling of burnout from over-immersion in HIV at both personal and professional levels, and diminished self care. Barriers to seeking support included: concerns regarding confidentiality; self-imposed and enacted stigma associated with accessing mental health services; and boundary issues resulting from changes in relationships with peers and other service providers. Evolving support mechanisms included: new formal and informal peer support networks amongst colleagues or other PHA service providers to address both personal and professional challenges, and having access to professional support offered through the workplace. The findings suggest the need for increased organizational recognition of HIV support work as a form of emotional labor that places complex demands on PHA service providers. Increased access to employer-provided mental health services, supportive workplace policies, and adequate job-specific training will contribute to reduced work-related stress. Community level strategies that support expansion of social networks amongst PHA service providers would reduce isolation. Systemic policies to increase access to insurance benefits and enhance sector-wide job preparedness and post-employment support will sustain long-term and meaningful involvement of PHAs in service provision.