This paper examines the empirical associations of a relatively broad and inclusive list of personality-related problems with both the high and low poles of the five-factor model of personality (FFM). Several studies have documented links between impaired functioning and the FFM, but these associations have largely been confined to the socially undesirable poles. In this study, a list of 310 personality-related problems was developed and administered to a large college student sample along with the International Personality Item Pool Representation of the Revised NEO Personality Inventory (IPIP-NEO) and an experimental manipulation of the NEO PI-R items (EXP-NEO). Numerous problems were associated with both poles of each trait domain and facet of the FFM, but both the IPIP-NEO and EXP-NEO were required to capture problems at both ends. Potential implications of emphasizing problems at one or both poles of trait continua are discussed. Future research should evaluate the structure and inclusiveness of the current list of personality-related problems against other representations of problem behavior, examine base rates of problems in other populations, and seek to understand the psychological mechanisms that might explain associations of problems across the full range of trait continua.