Since psychopathy poses major problems to society, it is of importance to gain more insight in this construct, which might be established by increasing knowledge of its neurocognitive underpinnings. Psychopathy may be related to failure to incorporate and learn from subtle or ambiguous feedback, which may lead to diminished awareness of potentially harmful consequences of choices. In result, this could induce increased risk-taking and decreased capability to adapt such behaviour. The aim of the present study was to investigate if a relation exists between psychopathic personality traits and risky decision making tendencies, and how this relation can be differentiated along specific symptoms of the psychopathic spectrum. Male prisoners (N = 119) completed a neuropsychological assessment of decision making tasks (the Iowa Gambling Task [IGT] and the Wisconsin Card Sorting Task [WCST]) as well as a self-report measure for dimensional psychopathic personality traits (Psychopathic Personality Inventory – Revised). In line with some of the previous literature, no significant correlations were found between measures of psychopathy on the one hand, and measures of decision making on the other hand. Other variables, such as age (with a negative correlation) and presence of a history of drug abuse did contribute significantly in the prediction of the total amount of psychopathic personality traits. Implications for interpretation of previous studies and strengths and limitations of the present study are discussed. The literature on the topic of decision making and psychopathy is now building up, but leaves inconsistent and certainly no convincing consensus. Future studies on psychopathy and neurocognition may need to shift away from traditional decision making tasks and instead focus more on experimental, ‘pure’ neurocognitive measures to better identify how specific cognitive pitfalls in psychopathy influence behaviour and ability to learn.