Early career teachers experience exceptionally high rates of attrition from the profession, often due in part to elevated concerns about student behavior and poor occupational health. This study reports findings from a randomized controlled trial testing the combined effect of the PAX Good Behavior Game and MyTeachingPartner™ for 188 early career, early elementary teachers (Grades K–3). Of primary focus were observations of the quality of teachers' interactions with students and their self-reported occupational health over 2 consecutive school years. Results indicated that relative to comparison teachers, those in the intervention condition reported lower distress at follow-up (d = −0.23) and less decline in teacher affiliation across the 2-year period (d = 0.50). In addition, the intervention teachers who were highly distressed at baseline and who experienced high levels of disruptive behavior had higher quality interactions with students around emotional support (d = 0.27), classroom organization (d = 0.32), and instructional support (d = 0.69) at the end of 2 years than comparison teachers. This subgroup of intervention teachers also experienced more favorable changes over time in distress (d = −2.47) and teacher affiliation (d = 3.00) over the course of the study. Professional development focused on classroom management with coaching support may be particularly impactful for early career teachers experiencing higher levels of distress and in classrooms with higher rates of behavior problems.