Tailoring information to a target individual's features is a promising line of development in self-help interventions. In this article, 752 smokers with explicit low intention to quit were randomly assigned to 1 of 5 conditions: (a) multiple tailored letters with self-help guide, (b) multiple tailored letters only, (c) a single tailored letter with a self-help guide, (d) a single tailored letter only, or (e) a nontailored intervention. Follow-up assessment took place 4 months after the intervention. Results indicated that the single tailored intervention only had no surplus value compared with a nontailored look-alike intervention. The addition of a self-help guide to a tailored intervention was only useful in highly dependent smokers, and multiple tailoring was more effective than single tailoring. It remains important to elucidate why and for whom certain tailored interventions are more effective.