Doubt can modulate our decision-making process. Although conceptually different, conflict (choice similarity: difficult or easy) and uncertainty (individual reward-likelihoods: uncertain or certain) are commonly related and often conflated. By posing as an evidence-accumulation problem, we assessed doubt, dissociating contextual conflict, and uncertainty and showed obsessive-compulsive disorder patients have specific impairments while processing difficult-uncertain contexts. It remains unclear whether this deficit is disorder-specific or a reflection of broader mental-health dimension. Multi-dimensional trans-diagnostic approaches help to tease out the mechanistic nature (specific or usual) of clinical observations and their validity in sub-clinical populations. Here, we first aimed to validate our conflict-uncertainty analysis approach in a larger non-clinical cohort (n>1300). Second, we assessed the relationship between decisional-parameters of difficult-uncertain contexts and a trans-diagnostic factor capturing individual differences in ‘compulsive-behavior and intrusive-thoughts’. We replicate our previous findings in a large, general population sample and highlight that the amount of evidence accumulated in difficult–uncertain scenarios increases functionally with compulsive-behavior and intrusive-thought emphasizing greater cautiousness. We further show that those with high social-withdrawal tendencies gather less evidence irrespective of context reflecting a ‘jumping to conclusions’ tendency in judgment. We attempt to bridge the gap between behavior and psychological markers by integrating trans-diagnostic and computational methods.