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The Five-Factor Model (FFM) is a dimensional model of general personality structure, consisting of the domains of neuroticism (or emotional instability), extraversion versus introversion, openness (or unconventionality), agreeableness versus antagonism, and conscientiousness (or constraint). The FFM is arguably the most commonly researched dimensional model of general personality structure. However, a notable limitation of existing measures of the FFM has been a lack of coverage of its maladaptive variants. A series of self-report inventories has been developed to assess for the maladaptive personality traits that define Diagnostic and Statistical Manual of Mental Disorders (fifth edition; DSM–5) Section II personality disorders (American Psychiatric Association [APA], 2013) from the perspective of the FFM. In this paper, we provide an introduction to this Special Section, presenting the rationale and empirical support for these measures and placing them in the historical context of the recent revision to the APA diagnostic manual. This introduction is followed by 5 papers that provide further empirical support for these measures and address current issues within the personality assessment literature.