We present two recent successfully litigated malpractice cases in which patients with cerebrovascular accidents were misdiagnosed as stroke mimics. The first was diagnosed as a hemiplegic migraine, which occurs in only 0.01% of the population. The second was diagnosed as a conversion disorder, which ultimately has a neurologic etiology in 4% of cases. In both cases, issues of poor patient communication and poor documentation were paramount in the legal outcome. We discuss caveats of stroke mimics, tissue plasminogen activator administration liability, and pitfalls in patient and family interactions.