Individuals randomized to TAMI will interact with the fully automated, web-based MI-chatbot for the 6-month study period. Patients who continue to smoke will receive up to two text messages per week with the chatbot URL link to initiate additional conversations always beginning with an assessment of readiness to change but "remembering" prior conversations much like a clinician. Individuals in the preparation stage will move directly to EBP education, tailoring a quit plan and boosting both self-efficacy and outcome expectancies. Patients with sufficient confidence will be encouraged to set a quit date. Patients will be encouraged to include their PCP and/or state quitline. TAMI will provide support proximal to the quit date including guidance through common obstacles. TAMI will check back to assess treatment initiation, treatment sustainment (and/or cessation), or relapse. Patients who are unable to quit (or who relapse) will be encouraged to restart conversations with TAMI.

Individuals randomized to the Usual Care (UC) condition will receive a detailed educational handout on the health risks associated with smoking and information on Evidence Based Practice's (EBP) for cessation using the standard "Kick-It California" materials. Additional materials and referral resources regarding depression, stress, and other common barriers will be provided to all UC participants. Any UC individual can choose to quit at any time but they will not have access to TAMI. While this is not an "active" treatment condition, the handout and recurring assessments (at 3 and 6mo) may serve as reminders about the importance of quitting and may assist with finding support for co-occurring conditions or social needs.

The investigators address the problems of intrinsic motivation, Evidence Based Practice (EBP) education, and referral tailoring using a digital-coaching intervention that 1) promotes readiness to change, 2) educates and builds confidence about EBP's, and 3) creates a tailored quit plan sensitive to social obstacles and needs.

The primary clinical outcome is 7-day point prevalence abstinence (PPA) from smoking at 6-months. Abstinence will be biochemically verified with salivary cotinine.

To maximize the validity of our primary abstinence outcome, the investigators will require any participant in who reports abstinence at 6-month to complete salivary cotinine bio-verification using a mailed, commercially available test kit. Participants will be instructed to electronically send two photos - one of them giving a saliva sample and the other with the test results. Recent reviews of biochemical verification strategies have validated this methodology. People with at least 10 ng/ml cotinine in their saliva will be considered smokers. The investigators will ask participants to report any Nicotine Replacement Therapy use or vaping to identify false positives.

Self-reported point prevalence abstinence (PPA) from smoking at 3-month

Self reported smoking reduction (# cigs, >50% reductions, and # quit attempts). Change = (score at time point - score at baseline)

Self reported demographics

The Working Alliance Inventory is a validated, self-reported 12 item instrument measuring three key aspects of the therapeutic alliance: (a) agreement on the tasks of therapy, (b) agreement on the goals of therapy and (c) development of an affective bond. Possible scores range from 1 (seldom) to 5 (always).

Change = (score at time point - score at baseline)