The likelihood of an outcome (uncertainty or sureness) and the similarity between choices (conflict or ease of a decision) are often critical to decision-making. We often ask ourselves: how likely are we to win or lose? And how different is this option's likelihood from the other? Uncertainty is a characteristic of the stimulus and conflict between stimuli, but these dissociable processes are often confounded. Here, applying a novel hierarchical drift diffusion approach, we study their interaction using a sequential learning task in healthy volunteers and pathological groups characterized by compulsive behaviours, by posing it as an evidence accumulation problem. The variables, Conflict (difficult or easy; difference between reward probabilities of the stimuli) and Uncertainty (low, medium or high; inverse U-shaped probability-uncertainty function) were then used to extract threshold ('a', amount of evidence accumulated before making a decision) and drift rate ('v', information processing speed) parameters. Critically, when a decision was both difficult (high conflict) and uncertain, relative to other conditions, healthy volunteers unexpectedly accumulated less evidence with lower decision thresholds and accuracy rates at chance levels. In contrast, patients with obsessive-compulsive disorder had slower processing speeds during these difficult uncertain decisions; yet, despite this more cautious approach, performed suboptimally with poorer accuracy relative to healthy volunteers below that of chance level. Thus, faced with a difficult uncertain decision, healthy controls are capable of rapid possibly random decisions, displaying almost a willingness to 'walk away', whereas those with obsessive compulsive disorder become more deliberative and cautious but despite appearing to learn the differential contingencies, still perform poorly. These observations might underlie disordered behaviours characterized by pathological uncertainty or doubt despite compulsive checking with impaired performance. In contrast, alcohol-dependent subjects show a different pattern relative to healthy controls with difficulties in adjusting their behavioural patterns with slower drift rates or processing speed despite decisions being easy or low conflict. We emphasize the multidimensional nature of compulsive behaviours and the utility of computational models in detecting subtle underlying processes relative to behavioural measures. These observations have implications for targeted behavioural interventions for specific cognitive impairments across psychiatric disorders.