The current study offers preliminary insight into the efficacy of a technology-based question-asking, sexually transmitted infection (STI) prevention program to promote condom use and reduce the incidence of STIs. Participants were 104 college students who were provided safe sex information via 12, email messages, delivered over a four (4) week period. During information delivery, students were randomly assigned to a deep-level reasoning message condition or to a standard message condition. Students assigned to the deep-level reasoning condition were prompted by a question, prior to the delivery of each email message while those assigned to the standard message condition received the email message without a question prompt. Students in the deep-level reasoning condition showed greater ease in suggesting condom use to their partner, were more likely to get tested for an STI and to use a condom during vaginal sex. Those in the standard message condition reported more condom use during anal sex at post-test. These findings suggest that technology-based (email delivered) STI interventions can be used to facilitate positive behavioral change.