Older women with HIV face challenges to their quality of life, including neurocognitive decline, early-onset menopause, and chronic health issues. Chief among these concerns is depression, the most common psychiatric comorbidity among people living with HIV, with rates twice as high among women as men. However, tailored interventions among older women living with HIV and depression are lacking. Following the ADAPT-ITT framework to adapt existing interventions for cultural relevance among groups of people living with HIV, the study team revised an evidence-based intervention, the ‘Stress Management and Relaxation Training/Expressive Supportive Therapy Women’s Project (SMART/EST),’ for online implementation. Working with two community stakeholders, the study team conducted focus groups, theater testing, and manual adaptation. This resulted in the development of e-SMART/EST, an online teletherapy group co-facilitated by a Licensed Psychologist and a credentialed Peer Counselor. The adapted, eight-session weekly intervention was tested with an exploratory pilot sample of eight older women (55 years and older) with HIV and depression. Participants rated the acceptability, feasibility, and appropriateness of the intervention, as well as symptoms of depression and HIV-related quality of life before and after the group. The e-SMART/EST Women’s Project demonstrated high acceptability, feasibility, and appropriateness. Engagement was high, as women attended an average of 6.8 sessions. In qualitative interviews, participants reported peer co-facilitation, culturally relevant themes (e.g., HIV-related minority stress, critical consciousness, grief, and sex and pleasure), mindfulness techniques, and cohesion with other women as main favorable elements of the intervention. Barriers to online implementation included technological issues, distractions due to remote participation, and hindered emotional attunement compared with in-person group therapy. Findings support further research to test similar interventions in full-scale trials with older women living with depression and HIV.