While promising, the evidence in support of tailored health communication has not been overwhelming. One explanation is that tailored materials may be far superior to non-tailored materials in some cases, but only slightly better, no different or less effective in others. In this study, 198 overweight adults were randomly assigned to receive either tailored or non-tailored weight loss materials. Participants' cognitive, affective and behavioral responses to the materials were measured at an immediate and 1 month follow-up. Analyses compared those who received tailored materials to those who received non-tailored materials that were--by chance alone--either a good fit, moderate fit or poor fit, based on the match between behavioral characteristics of the participant and content of the non-tailored materials. Findings showed that good-fitting non-tailored materials performed as well or better than tailored materials for several cognitive, affective and behavioral outcomes. However, moderate- and poor-fitting non-tailored materials were consistently inferior to both approaches. The art and science of creating tailored health communication programs is still evolving. Data from this study suggest present approaches to tailoring are more effective than non-tailored materials in most, but not all cases. Specific recommendations are made describing ways to refine tailoring methods to maximize the effectiveness of this approach.