It is a health education truism that instructional material will be more effective when audience characteristics are taken into account at the outset of program development. One strategy for disseminating relevant health information to individuals is known as "tailored messaging," which accounts for intra-individual information processing needs. This customized approach to health communication is proposed to catch individuals' attention and have a positive effect on cognitive-behavioral responses to health information. Because of the increased attention this communication strategy has received within the recent health education literature, this paper (1) revisits the origins of tailored communication, (2) contrasts tailored versus targeted communication, (3) outlines potential problems and weaknesses of tailoring, (4) discusses challenges associated with implementing and evaluating tailored health interventions, and (5) proposes a path and recommendations for the future of tailored messaging in health education. Future research should consider developing empirical models of tailoring to help clarify pathways for successful application. In addition, health education researchers should come to a consensus regarding whether tailoring represents a cost- effective, feasible alternative to targeted messaging. (Contains 4 tables.)