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BackgroundTobacco use remains the leading cause of preventable mortality in the United States; yet, evidence-based cessation services remain underused due to staffing constraints, limited access to counseling, and competing clinical priorities. Generative artificial intelligence (GenAI) chatbots may address these barriers by delivering personalized, guideline-aligned counseling through naturalistic dialogue. However, little is known about how GenAI chatbots support smoking cessation at both outcome and communication process levels. ObjectiveThis feasibility study evaluated the implementation of an evidence-based smoking cessation counseling session delivered by a GenAI-powered chatbot, Aipaca. We examined (1) pre-post changes in cessation preparedness, (2) communication dynamics during counseling sessions, and (3) user perceptions of the chatbot’s value, limitations, and design needs. MethodsWe conducted an observational, single-arm, mixed methods study with 29 adult smokers. Participants completed pre-post surveys measuring knowledge of smoking-related health risks and cessation methods, self-efficacy, and readiness to quit. Each engaged in a 30-minute text-based counseling session with Aipaca, powered by GPT-4 and structured using the 5A’s framework (Ask, Advise, Assess, Assist, Arrange). Sessions were transcribed for microsequential conversation analysis. Twenty-five participants completed semistructured interviews exploring perceived value, challenges, and design suggestions. Quantitative data were analyzed with paired-samples t tests, qualitative data were thematically analyzed, and transcripts were analyzed for interactional practices. The methodological strength of this study lies in its triangulated approach, which combines quantitative measurement of intervention effectiveness, qualitative analysis of user interviews, and conversational analysis of counseling transcripts to generate a comprehensive understanding of both outcomes and underlying mechanisms. ResultsParticipants demonstrated significant improvements in all preparedness indicators: knowledge of health risks, knowledge of cessation methods, self-efficacy, and readiness to quit. Conversation analysis identified three recurrent patterns enabling counseling-relevant dynamics: (1) contextual referencing and continuity, (2) formulations with elaboration prompts, and (3) narrative progression toward collaborative planning. Interview themes underscored Aipaca’s perceived value as an accessible, nonjudgmental, and motivating resource, capable of delivering personalized and interactive support. Criticisms included limited accountability, reduced cultural resonance, and overly goal-directed style. Participants emphasized design needs such as proactive engagement, gamified progress tracking, empathetic or anthropomorphic personas, and safeguards for accuracy. ConclusionsThis mixed methods feasibility study demonstrates that GenAI can deliver evidence-based smoking cessation counseling with measurable short-term gains in cessation preparedness and process-level communication patterns consistent with motivational interviewing. Users valued Aipaca’s accessibility, empathy, and personalization, while also articulating expectations for richer social roles and long-term accountability. Findings highlight both the promise and challenges of integrating GenAI into digital health: pairing adaptive language generation with human-centered design, embedding accuracy safeguards, and ensuring integration into multilevel cessation infrastructures will be essential for future clinical deployment.