A user data engine residing on an endpoint machine generates a current user context reflecting a specific flow of operations performed by an end-user when interacting with a software application. A context engine residing on a sever machine compares the current user context to one or more stored user contexts included in a context database and generates a similarity value based on each comparison. A resource engine identifies resources in a resource database that are associated with the stored user contexts and then generates a relevance score for each resource based on the similarity scores corresponding to the stored user contexts with which those resources are associated. The resource engine transmits a resource list reflecting the identified resources to the user data engine based on the relevance scores. The user data engine displays on a display screen of the endpoint machine information associated with resources reflected in the resource list.