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Objectives. We assessed factors associated with engagement in transactional sex among men who have sex with men recruited from one of the largest Internet sites for men seeking social or sexual interactions with other men in Latin America. Methods. We constructed multilevel logistic regression models to analyze factors associated with engagement in transactional sex in 17 Latin American countries in 2012. Results. Of 24 051 respondents, 1732 (7.2%) reported being paid for sexual intercourse in the past 12 months. In a multivariable model, higher country-level unemployment was associated with increased odds of transactional sex (adjusted odds ratio [AOR] = 1.07 per 1% increase in unemployment; 95% confidence interval [CI] = 1.00, 1.13). Individual or interpersonal factors associated with increased odds of engagement in transactional sex included self-reported HIV (AOR = 1.33; 95% CI = 1.04, 1.69) or sexually transmitted infection (AOR = 1.33; 95% CI = 1.11, 1.59), childhood sexual abuse history (AOR = 1.75; 95% CI = 1.48, 2.06), intimate partner violence (past 5 years, AOR = 1.68; 95% CI = 1.45, 1.95), and sexual compulsivity (AOR = 1.77; 95% CI = 1.49, 2.11). Conclusions. Structural-level economic interventions and those that address individual and interpersonal factors may improve HIV prevention efforts among men who have sex with men who engage in transactional sex. (Am J Public Health. 2015;105:e95–e102. doi:10.2105/AJPH.2014.302402) [ABSTRACT FROM AUTHOR]