Introduction Despite a decline, smoking rates have remained high, especially in communities with lower income, education, and limited insurance options. Evidence shows that physician-initiated counseling on smoking cessation is effective and saves lives, and that specific skills are needed to appropriately lead this type of patient-physician communication. Residency is a critical moment for future physicians and may be the optimal time to learn, practice, and refine this skillset. Unannounced Standardized Patients (USPs) have been found to be effective, incognito evaluators of resident practices. Methods This study introduced rigorously trained actors (USPs) into two urban, safety-net clinics to assess resident ability to engage, activate, and counsel a pre-contemplative smoker. A complementary chart review assessed appropriate documentation in the patient's electronic health record (EHR) and its relationship to counseling style and prescribing practices. Results Resident scores (% well done) on patient education and engagement were low (33% and 23%, respectively). Residents who coupled cessation advice with an open discussion style activated their patients more than those who solely advised cessation across all comparable measures. On EHR documentation, residents who accurately documented smoking history were more likely to directly advise their patient to quit smoking when compared to residents who did not document (t(97) = 2.828, p = .006, Cohen's D = 0.56). Conclusions Results highlight the need to reinforce training in patient-centered approaches including motivational interviewing, counseling, and shared decision-making. Future research should focus on the effects of smokers in pre-contemplation on physician counseling style and examine the relationship between medical training and provider communication to guide interventions.