We review briefly the contributions of Skodol, Pincus, and Widiger (this issue) describing and critiquing the proposed changes in the assessment of personality and personality disorders for the DSM-5. Despite the hard work of the DSM-5 Work Group to date, there are shortcomings and areas of controversy in the current proposal that demand further attention and change. We discuss the controversy in the broader context of the DSM over the past 30 years. In addressing specific problems, we focus on the limitations of the proposed system for assessing traits (even as we endorse the movement toward dimensional assessment of personality) and the difficulties posed by the current "hybrid" model that attempts to include both traits and types. In moving forward, we suggest greater emphasis on decision-making regarding the presence and severity of any personality disorder (understood on the basis of generalized failures in adaptation) and greater flexibility in identifying the variants of personality disorders in order to accommodate both traits and types more inclusively during this transition toward dimensional approaches to assessment.