Recent research had indicated that treatment of psychopaths in therapeutic communities was problematic in terms of high rates of attrition, low levels of motivation, and increased reconviction. This paper reports on the development of a checklist (included in the article) completed by prison officers designed to measure behaviors associated with poor adjustment to a prison-based therapeutic community. Behavior checklist scores showed statistically significant correlations with the Hare Psychopathy Checklist Revised (1991), particularly with Factor 1 scores measuring interpersonal aspects of psychopathy. The paper discusses the potential for developing this method as a type of dynamic assessment for psychopaths undertaking treatment. It concludes that the checklist may be extended in future research to target the behaviors shown by psychopaths in therapeutic community settings and to assess whether there is behavioral change in psychopaths as a result of therapeutic intervention. Tables, references, note, appendix