Certain embodiments present a system for generating a medical teaching file message. An image identifier labels medical images based upon information pertaining to user interaction with the image. The system also provides an image search engine that scans and indexes images within a database based on a set of rules. The image search engine generates a subset of images from a larger group of medical images within a database based upon the rules. The system also includes a supporting data selection engine for accepting a free text search query from an interface. The supporting data selection engine scans medical databases based on the free text search query, and provides the supporting data search results via an interface. A teaching file message is generated either automatically or manually from the subset of images and the supporting data search results for transmission to a teaching file.