The prohibition and legalization of cannabis operate on a continuum. This book chapter analyzes the dynamics unique to—and shared by—prohibition and legalization. First, it investigates how each regime works by looking at its effects. Second, it explains the role each policy regime plays in its political-economic context. Finally, it analyzes how prohibition’s dynamics are altered or rearticulated through and after legalization. The chapter relies on and underscores the importance of ethnographic approaches in understanding the continuities and discontinuities between prohibition and legalization.