Abstract Objective The detrimental impact of in utero substance use on developing fetuses manifests well into adolescence (Wu, Ju, & Lu, 2011; Minnes, Lang, & Singer, 2011). Likewise, the effects of early childhood neglect during critical developmental periods may be long lasting (de Bellis, et al., 2009; Hildyard & Wolfe, 2002). Factors such as these may require creative adaptation of assessment. This case illustrates the process of evaluating a child presenting with an unusual developmental history and extremely challenging behaviors and describes efforts to maintain engagement while eliciting valid data. Successful and unsuccessful interventions will be reviewed. Method Patient is a 12-year-old Caucasian male admitted to a state psychiatric hospital with a complex presentation of emotional, behavioral, and cognitive difficulties. Aggravating factors consist of likely in utero drug and alcohol exposure, early trauma, chronic neglect, and unusually small physical stature. Neuropsychological evaluation was completed over the course of five days. Testing sessions were brief, on a unit where no one was present, and were structured using both intermittent and scheduled reinforcement to maintain effort and engagement. Results Testing indicated significant and consistent weaknesses in executive functioning, learning, memory, and attention. Despite the use of stimulant medication, difficulty with vigilance, sustained attention, and impulsivity persisted. Diagnoses were Neurodevelopmental Disorder associated with prenatal substance exposure, Generalized Anxiety Disorder, Attention Deficit/Hyperactivity Disorder, Combined presentation, and Oppositional Defiant Disorder, Moderate. Conclusions Unconventional history warrants unconventional approach to assessment. Recommendations included not only approaches to improving his attention, but just as important, strategies to elicit his best performance in various settings.