PositiveLinks (PL) is a mHealth platform to support care engagement by people with HIV (PWH). Daily reminders prompt the user to report medication adherence, mood, and daily stress. Higher response rate to PL check-ins has been associated with better suppression of viral load over 6-18 months. We conducted a retrospective chart review for a three-year period collecting demographic information, average mood and stress scores, and all viral loads obtained in usual patient care. We performed multivariable logistic regression modeling to identify factors associated with loss of viral load suppression and a time-to-event survival analysis until first unsuppressed viral load stratified by PL usage. Of the 513 PWH included, 103 had at least one episode of viral non-suppression. Low users of PL were more likely to have an unsuppressed viral load with an adjusted Odds Ratio (aOR) of 5.8 (95% CI 3.0-11.5, p < 0.001). Protective factors included older age (aOR 0.96; 95% CI 0.93-0.98, p = 0.003) and income above the federal poverty level (FPL) (aOR 0.996; 95% CI 0.995-0.998, p < 0.001). High PL use was also associated with better viral load suppression (VLS) over time (p < 0.0001 ((aHR) of 0.437 (95% CI 0.290-0.658, p < 0.001)) after adjusting for age and FPL. High stress scores were related to subsequent loss of viral suppression in an exploratory analysis. High check-in response rate on the PL app, older age, and higher income are associated with sustained VLS over time. Conversely, lack of response to check-ins or increased reported stress may signal a need for additional support.