In addition to consistent use, condoms must be used correctly. The purpose of this study was to identify prevalence and types of condom-associated discomfort among university students, the outcomes of this discomfort, and the role of discomfort in condom breakage. We conducted a cross-sectional study of 206 students attending a private university in the southern United States. We assessed 3 potential outcomes: breakage, not using condoms throughout sex, and low condom-use motivation. Nearly one third reported discomfort, including tightly fitting condoms, vaginal irritation, and Joss of sensation. Discomfort was associated with breakage (p = .0001), incomplete use (p = .0001), and less motivation to use condoms (p = .018). Gender moderated the latter 2 findings. Adjusted findings indicate that students reporting discomfort were 3.6 times more likely to also report breakage (p = .0009). Continued investigation of this topic is warranted. Prevention education may benefit university students by promoting several key practices, such as adding lubricant to condoms before they dry out and acquiring condoms that fit properly.