Psychopathic personality traits have been identified as an important predictor of associative learning capacity. Prior work has associated psychopathy with deficits when adapting learned associations in response to novel information. However, findings are inconsistent and are hypothesised to vary as a function of the processing load created by different experimental paradigms. We tested this hypothesis by examining the association between psychopathic traits and Stimulus-Response-Outcome contingency learning whilst manipulating contextual processing load. In experiments one and two, participants completed three versions of a configural object discrimination task that required participants to use increasingly multidimensional learning cues. Across both experiments, it was found that elevated levels of psychopathic traits were associated with a lesser capacity to form S-R-O associations in the bidimensional but not tridimensional versions of the learning task. This suggests psychopathy-related learning deficits may vary as a function of the processing load inherent to the bidimensional learning environment, rather than the type of learning taking place. This provides some of the first experimental evidence that psychopathic learning deficits are detectable during the acquisition phase of learning.