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Digital smoking cessation interventions frequently use automated delivery of content. Integrating a counselor may improve participant engagement and facilitate health behavior change. We investigated engagement with live counseling compared to automated content in a Facebook intervention and the impact of engagement on smoking cessation outcomes. The Tobacco Status Project is a 90-day smoking cessation intervention for young adults utilizing automated posts and weekly sessions with a live counselor in Facebook groups tailored to readiness to quit (precontemplation, contemplation, preparation). Data came from the treatment group of a randomized trial. Post-level analyses investigated participant engagement (number of comments) by post type (e.g., counselor posts or automated posts based on transtheoretical model of behavior change, clinical practice guidelines, motivational interviewing), stratified by readiness to quit. Participant-level analyses examined whether extent of participant engagement with counselor posts predicted abstinence at 3 months. We analyzed data of N = 251 participants and N = 2,941 posts, 11% of which were live counselor initiated, and together generated 8,403 comments. Post-level analyses found that compared to the most engaging automated content (motivational content for precontemplation and contemplation, informational content for preparation), live counseling generated more engagement among participants in preparation, similar engagement in precontemplation, and less engagement in contemplation. Extent of live counseling participation predicted 3-month verified abstinence (adjusted OR = 1.10, 95% CI [1.02, 1.20]). In digital interventions, counselor contact may be beneficial in addition to automated posts at yielding engagement and abstinence; however, participants engage differently with counseling according to readiness to quit.