Multiple medications are known to increase epileptogenicity in patients with and without an underlying seizure disorder. Paradoxically, some of these medications include anti-seizure medications (ASMs) and other medications, such as psychotropics, that act on the central nervous system (CNS). This article aims to discuss 3 clinical cases that highlight the gamut of epileptogenic reactivity secondary to CNS drugs ranging from increased epileptogenicity in the form of interictal epileptiform discharges (IEDs) without seizures, increased epileptogenicity on electroencephalogram (EEG) with associated non-epileptic movement disorders, and frank, de novo seizures. We also analyze the relevant literature on the impact of CNS medications on epileptogenicity.