Background: Men who have sex with men (MSM) have an increased risk for sexually transmitted infections (STIs) and are disproportionately affected by the human immunodeficiency virus (HIV) Resultsing from risky sexual behaviors (RSB). There is a dearth of information about the prevalence of RSBs among men who have sex with men in Uganda. Therefore, we explored risk sexual behaviors among MSM in urban Uganda. Methods: Using exploratory qualitative design and snowball sampling, 20 men who had sex with men from Lesbian, Gay, Bisexual, Transgender, Queer/Questioning associations around Kampala and Wakiso districts consented to participate in in-depth interviews. The recorded interviews were transcribed verbatim and analyzed using qualitative content analysis. Coding was done using Open Code software version 4.03. Codes and categories were developed. Results: Risky sexual behaviors were highly prevalent, especially among the young men (20-25 years). The most common risky sexual behaviors reported included transactional sex, which was facilitated by dating apps and mediated by the need for financial support because most of them were rejected by their families. Group sex and having sexual intercourse when drunk were commonly reported and were mediated by the need for social acceptance and support. Some respondents reported having sex with females to avoid being suspected by their families. Knowledge of sexually transmitted infections was low, especially for respondents outside of Kampala in Wakiso. Conclusions: There are key implications for HIV/STI transmission Resultsing from RSBs among MSM, worsened by difficulty in obtaining information and implementing preventive measures due to intense social stigma and social isolation. Effective interventions, including the use of social dating apps to ensure increased access to health awareness messages and access to condoms, lubricants, and pre-exposure prophylaxis, are urgently needed to limit the consequences of MSM as a bridge for HIV transmission to the general population.