Abstract: A system and method of presenting context-sensitive learning assets, such as videos or other files, in a user interface. The user interface components send an identifier of the context of a user interface to a learning platform, which is used to identify content descriptors for the appropriate learning assets. The content descriptors are sent back to the user interface, where the learning assets described by the content descriptors can be viewed by the user. The system and method uses one of three modes for creating content descriptors. In Static Mode, a unique identifier is sent from the user interface and the content descriptors that are identified by that identifier are returned. In Dynamic Metadata-Driven Mode, metadata is sent, and rules determine which content descriptors are returned. In Dynamic Content-Driven mode, the entire page content being viewed is analyzed and specific search algorithms determine which content descriptors are returned.