An increasing number of smokers are obtaining information from the web to help them quit smoking. In this study, we examined how smokers process different types of messages similar to those from a web-based smoking cessation program: personalization/feedback ("Jane, you are a 23-year old female smoker"), motivational ("If you quit smoking, you could save $1200 a year"), and instructional ("When you feel angry, talk to someone instead of smoking") messages. Using functional magnetic resonance imaging, smokers were exposed to the messages. On a later session, participants completed an online tailored smoking cessation program and started on a 10-week course of nicotine patch. Results show that participants indeed process the messages differently, activating brain regions associated with self-related processing (personalization/feedback), anticipated reward processing (motivational messages) and rules processing (instructional messages). This research is relevant for advancing web-based tailored interventions for substance use.