Advances in artificial intelligence and computing technologies has made it entirely possible to provide personalized health education and individualized learning on a mass scale. Interactive web technology not only provides an opportunity to present tailored health information in a number of formats, but it also provides the greatest ability to toggle between modalities, further enhancing learners' experiences and understanding of the material. However, development and deployment of these types of approaches often requires a high capital overlay or initial investment. This cost, however, is often justified based on wide assumptions about its effectiveness for achieving learning outcomes (e.g., mastery and deeper understanding of the course material). But, while there is growing evidence about the efficacy of computer-tailoring and adaptive learning environments on learning, we have yet to fully understand the mechanisms by which this affects how individuals process information. This paper presents preliminary results of a randomized controlled trial testing effects of a tailored educational site on human sexuality on the comprehension and elaboration of the health content by middle schoolers. The project is one of the first attempts to systematically tease out the effective components of a tailored health education website and to examine its effects singly and in combination on the comprehension of a complex health domain.