This written description of an analysis conducted while the analyst was in analytic training demonstrates the complexities of treating patients with attention deficit hyperactivity disorder (ADHD). This discussion focuses on that treatment and the treatment of similar patients in whom cognitive deficits have influenced development and led to difficulties with affect regulation and behavioral inhibition. These patients often fear a loss of control during an analytic regression that might expose the deficits that they have felt to be shameful. They might require a longer preparatory therapy before a transition to analysis, to gain a sense of trust and safety in the therapeutic process and to decrease their shame sensitivity. The analyst’s confusion in the countertransference often mirrors the patient’s lifelong confusion because of his deficits, and is a hallmark in such treatments. This analyst demonstrated significant analytic perspective as she reexamined her experience during the writing about it.