We examined product adherence among 187 men who have sex with men and transgender women enrolled in a phase II, crossover trial comparing safety and acceptability of an oral tablet and a rectal gel used daily for HIV prevention. Participants reported adherence via daily text messages during 8-week periods. Trajectory analysis identified weekly patterns. Polytomous logistic regression identified characteristics associated with higher probability of trajectory group membership. We identified 3 groups per product: high-adherers (72% daily oral, 70% daily gel); decreasing-adherers (20% daily oral, 22% daily gel); and low-adherers (8% daily oral, 9% daily gel). Daily oral high-adherers (compared with low-adherers) were more likely to self-identify as male (OR = 4.76, 95% CI:1.35–16.67), to have more sexual partners (OR = 1.67, 95% CI:1.04–2.63), and to find the tablet easy to swallow (OR = 2.22, 95% CI:1.08–4.76). Daily gel high-adherers (compared with low-adherers) were more likely to be older (OR = 1.16, 95% CI:1.05–1.28), to find gel application easier at the last few applications (OR = 2.27, 95% CI:1.01–5.00), and to report a change in routine if gel was not used (OR = 5.26, 95% CI:1.23–100.00). Characteristics of participants likely to be high-adherers to product use vary according to product. Evaluation of acceptability prior to phase II/III trials could identify participants likely to maintain high adherence.