Frontline healthcare practitioners face their own rendition of “Thunder Road” when it comes to providing quality pain management for their patients. It’s 2021, and we’re still in the middle of a pandemic, an economic roller-coaster, and the fledgling era of “legal weed.” Does “legal” mean truly legal when it comes to cannabis, whether medical or recreational? What are the legal implications for a prescriber who actively treats patients with controlled medication knowing that the patient actively uses cannabis? What is the DEA’s position on cannabis and how does it impact medical decision-making? How do practitioners document their way through this gauntlet and show reasoned and sound efforts to individualize patient care? Using case examples and regulatory resources, we will examine basic navigation tools that will facilitate how to clinically and legally reconcile the treatment of patients with controlled substances in the face of growing patient access to cannabis, legal or not. The law’s penchant for documentation of the prescriber’s individualized patient care and demonstration of sound medical reasoning will serve as the compass for surviving the journey.