Lingering federal prohibition of cannabis sales and possession creates myriad problems for state-legal users. This is particularly the case for military veterans. The Department of Veterans Affairs (VA) has issued confusing guidance at times regarding the ability of veterans to access state-legal medical cannabis and how VA doctors can advise their patients. This paper will examine the ways that veterans can fall through the cracks in accessing state-legal medical cannabis for the treatment of service-related chronic illnesses like post-traumatic stress disorder (PTSD), chronic pain, and traumatic brain injury (TBI). It begins with a review of the research specific to cannabis as a treatment for PTSD, pain, and TBI. It then reviews the history and present scope of states that include these as approved conditions under their medical cannabis programs. The article then turns to discussing the evolving guidance provided by the VA to patients and doctors and federal restrictions on efficacy research. The article concludes by discussing the administrative burdens veterans face accessing state-legal medical cannabis and how they will be compounded as states begin legalizing medical uses for other controlled substances like psylocibin mushrooms and MDMA (ecstasy).