In this paper, a critical discussion is made of the role of entailments in the so-called New Paradigm of psychology of reasoning based on Bayesian models of rationality (Elqayam & Over, 2013). It is argued that assessments of probabilistic coherence cannot stand on their own, but that they need to be integrated with empirical studies of intuitive entailment judgments. This need is motivated not just by the requirements of probability theory itself, but also by a need to enhance the interdisciplinary integration of the psychology of reasoning with formal semantics in linguistics. The constructive goal of the paper is to introduce a new experimental paradigm, called the Dialogical Entailment task, to supplement current trends in the psychology of reasoning towards investigating knowledge-rich, social reasoning under uncertainty (Oaksford and Chater, 2019). As a case study, this experimental paradigm is applied to reasoning with conditionals and negation operators (e.g. CEM, wide and narrow negation). As part of the investigation, participants’ entailment judgments are evaluated against their probability evaluations to assess participants’ cross-task consistency over two experimental sessions.