Health communication researchers have shown that tailored health communication messages outperform nontailored materials. Non-tailored materials are typically “one-size-fits-all” messages designed to reach as much of the total audience as possible. Tailored materials are designed to match the needs and other factors of individuals. The technology used to perform this tailoring has traditionally been expert systems. This project suggests that a software agent approach will improve the delivery of tailored messages. Specifically, this work-inprogress paper discusses (1) the health communication and behavior change theories that apply to smoking cessation, (2) how those theories would be used in a software agent system, and (3) a proposed efficacy test of the system.