Various embodiments of the present invention provide methods, apparatus, systems, computing devices, computing entities, and/or the like for performing natural language processing (NLP) operations on multi-segment documents. For example, certain embodiments of the present invention utilize systems, methods, and computer program products that perform NLP operations on multi-segment documents by generating document segmentation machine learning models, using document segmentation machine learning models to determine document segments of input multi-segment documents, enabling adaptive multi-segment summarization of multi-segment documents, and enabling guided interaction with multi-segment documents.