BACKGROUND: Men who have sex with men (MSM) experiencing recurrent sexually transmitted infections (STIs) may play a crucial role in the STI epidemic. However, there is limited understanding of what kind of behavior leads to recurrent STIs. METHODS: A total of 179 MSM using preexposure prophylaxis were followed up for 18 months and were screened quarterly for chlamydia, gonorrhea, and syphilis from 2015 to 2018 in Belgium. Participants were stratified into 3 different groups (no STI, one STI episode, recurrent STI episodes during the study). Sociodemographic and sexual behavioral characteristics were compared between the 3 groups, and significant associations with recurrent STI were explored using multivariate logistic regression models. RESULTS: A total of 62.0% (n = 111/179) of participants experienced at least one STI during the study, and more than 1 in 3 became reinfected with an STI at another visit (n = 66/179 [36.9%]). Participants experiencing recurrent STIs reported the highest frequency of sexualized drug use (86.4%) compared with participants experiencing one (60.0%) or no STI (47.1%). Therefore, sexualized drug use was highly associated with recurrent STIs (adjusted odds ratio [aOR]. 4.35). Other factors associated with recurrent STIs were being younger than 40 years (aOR, 3.29), had a high number (>4) of nonsteady partners with whom receptive (aOR, 1.17) or insertive (aOR, 1.12) condomless anal intercourse occurred in the last 3 months. CONCLUSIONS: Sexualized drug use was the greatest risk factor for having recurrent STIs. Tailoring prevention and care, including specialized services tackling problematic drug use in a sexual context, may help to curb the STI epidemic among MSM.