In certain embodiments, document-based resolution of user inquiries may be facilitated. A predicted intent of the user is determined based on chat activity information associated with the user. A response to a user inquiry may be provided to the user via a chat interface based on the predicted intent. User response may be obtained for the response, which may indicate a failure in providing a resolution to the user (e.g., regarding a user inquiry). Upon detecting a failure in providing the resolution, a document associated with the user and matching the predicted intent may be obtained and presented to via the chat interface. The document may have content related to the predicted intent. The document may be presented as a response to the user response to seek a confirmation from the user regarding its relevance to the user inquiry.