Systems, computer-implemented methods, and computer program products to facilitate contextual comparison of semantics in conditions of different policies are provided. According to an embodiment, a system can comprise a processor that executes computer executable components stored in memory. The computer executable components can comprise a comparison component that contextually compares semantics of conditions in policy data of different policies based on a feature of at least one entity. The computer executable components further comprise a contextualization component that employs a model to provide a contextual explanation of how a first condition in first policy data of a first policy is semantically different from a second condition in second policy data of a second policy based on the feature of the at least one entity.