Purpose: This study examined adolescents' technology-based sexual communication with dating partners, and evaluated associations between technology-based communication and condom use. Methods: Participants were 176 high school students who indicated their use of technology to communicate with partners about condoms, birth control, sexually transmitted infections (STIs), HIV/AIDS, pregnancy, and sexual limits. Sexually active youth also reported their frequency of condom use. Results: Many adolescents (49%) used technology to discuss sexual health with partners, with rates varying by topic. Girls were more likely than boys to discuss HIV, pregnancy, and sexual limits. Ethnic minorities were more likely than whites to discuss condoms, STIs, HIV, pregnancy, and birth control. Importantly, rates of consistent condom use were three times higher among youth using technology to discuss condoms and birth control. Conclusions: Results provide novel preliminary evidence regarding adolescents' use of technology to discuss sexual health and demonstrate links between technology-based communication and condom use among sexually active youth. (C) 2014 Society for Adolescent Health and Medicine. All rights reserved.