Chronic pain is an important and understudied comorbidity in people living with HIV (PLWH). We conducted a pilot trial of Skills TO Manage Pain (STOMP), an innovative social cognitive theory-based pain self-management intervention tailored to PLWH, to assess feasibility, acceptability, and preliminary efficacy. Eligibility criteria included being HIV+, ≥ moderate pain for ≥ 3 months and a score of ≥ 4 on the three-item PEG pain severity and interference scale. Participants were randomized in a 1:1 fashion to STOMP or a usual care comparison. Among 22 participants randomized to STOMP, median session attendance was 9/12 (75%). Of 19 STOMP participants surveyed, 13 reported being “much better” overall since beginning treatment. Brief pain inventory-total scores decreased by 2 points in the intervention group and 0.9 in the control group (p = 0.11). STOMP is feasible, acceptable, and shows preliminary evidence of efficacy and promise for a full-scale trial.