Under the Controlled Substances Act (1970), the federal government classifies cannabis as a Schedule I drug with high potential for abuse and no accepted medical use. Meanwhile, thirty-five states have defied federal prohibition and approved cannabis use for either medical or medical and recreational purposes. States are chipping away at War on Drugs policies with little clear guidance from the federal government. The starkly divergent approaches to cannabis regulation lead to administrative challenges for adopting states and the budding industry. We examine how the federal government’s rhetorical and regulatory fickleness on cannabis policy has led to several downstream administrative consequences in banking, taxes, social equity, and bankruptcy protections. We also discuss whether recent events like the coronavirus pandemic and more state adoptions can accelerate change at the federal level. Finally, we argue for additional research attention to cannabis policy by federalism and public administration scholars.