Abstract: Many adolescents do not receive accurate and complete sexual health education in middle school. There are many barriers to traditional teacher-led sexual health education including lack of sexual health training for educators. Using web-based, self-directed learning (WBSDL) in a classroom setting is a novel approach to overcoming these barriers. Using a Case-Based Reasoning (CBR) or Goal-Based Scenario (GBS) design model, a WBSDL was designed, developed, and implemented to ensure that accurate health information is taught to middle school students and to decrease potential student embarrassment that may accompany group instruction. Student learning and satisfaction of the two sexual health lessons were evaluated, and analyses indicated overall positive findings for this instruction, as well as several gender differences.