Introduction: Previous research suggests that driving practice in diverse contexts may contribute to earlier licensure and improve driving skills among teen drivers. However, few studies have examined the role of practice diversity in driving outcomes post-licensure. Specifically, examining self-regulatory driving practices post-licensure may provide insight into the extent to which teens choose to avoid driving various environments. The current study examined the relationship between learner phase driving practice diversity and teen self-regulatory driving practices over the first six months of licensure. Methods: Fifty-six newly licensed 16-year-olds reported pre-licensure practice diversity, driving exposure and, self-regulatory driving practices at three timepoints (within 2 weeks of licensure and at 3 and 6 months post-licensure). Results: Multi-level models revealed self-regulatory driving practices significantly decreased over the first six months of independent driving. Practice in complex environments (e.g., on a commercial road, on a highway, etc.) was associated with fewer self-regulatory driving practices at baseline. Practice in simple environments (e.g., in a residential area, in a parking lot) was associated with more self-regulatory driving practices at baseline. Practice driving at night and in bad weather conditions predicted greater post-licensure self-regulation of driving in those specific environments. Conclusion: This study reinforces the importance of practice diversity for teens before independent driving, as early practice can have implications for self-regulatory driving practices immediately upon licensure. Future research examining this topic may inform parent-based interventions to maximize teen driver safety during the critical post-licensure period.