Abstract Background and Objectives Older people have an increased risk of developing frailty, an age-related clinical syndrome associated with worse health outcomes. This study examined the effect of self-perception of aging (ie, age discrepancy—individuals feel younger/older than their chronological age and aging satisfaction) on frailty transitions. Research Design and Methods We use longitudinal data from 549 HIV−/499 HIV+ sexual minority men aged 50 years or older enrolled in the Multicenter AIDS Cohort Study. To test the association of self-perception of aging on transitions between states of frailty (nonfrail/frail), defined using Fried Frailty Phenotype, a multinomial modeling was used. Results With remaining nonfrail as the referent group, participants reporting low aging satisfaction (vs moderate aging satisfaction) had increased odds of transitioning from nonfrail to frail (odds ratio [OR]: 2.72; 95% confidence interval [CI]: 1.56–4.74), frail to nonfrail (OR: 3.40; 95% CI: 1.62–7.12), or remaining frail (frail to frail; OR: 6.64; 95% CI: 3.88–11.38). Participants reporting older subjective age (vs no age discrepancy) had increased odds of transitioning from nonfrail to frail (OR: 2.50; 95% CI: 1.11–5.64), frail to nonfrail (OR: 4.47; 95% CI: 1.85–10.81), or remaining frail (frail to frail; OR: 5.68; 95% CI: 3.06–10.56). High aging satisfaction and younger subjective age were not statistically associated with frailty transitions. Discussion and Implications Our findings show that negative self-perception of aging (ie, older subjective age and low aging satisfaction) is associated with frailty transitions (nonfrail to frail, frail to nonfrail, and frail to frail) when compared to remaining nonfrail.