A real-time agreement comprehension tool is described. Initially, a user is selected as a signing party to an agreement. A document deployment system enables a computing device associated with the user to access the agreement. The computing device presents the agreement via a display device for digital signing by the user. While the agreement is presented, a voice assistant platform obtains a query from the user about at least a portion of the agreement. Responsive to the query, an agreement comprehension tool of the computing device determines an answer to the query by processing a limited set of documents that are relevant to the portion of the agreement. This limited set of documents includes a corpus of documents corresponding to the authoring organization and previous agreements with which the signing user has interacted. The agreement comprehension tool then causes the answer to be presented for display and/or audibly output.