1. A computer system, comprising: an endpoint machine that includes a user data engine (UDE) configured to: generate a current user context reflecting a first flow of operations performed by an end-user when interacting with a software application executing on the endpoint machine, and transmit the current user context to a context engine residing within a server machine; and the server machine that also includes a resource engine, a context database and a resource database, wherein the context engine is configured to: compare the current user context to a stored user context included in the context database, wherein the stored user context reflects a second flow of operations performed during a prior interaction with the software application or with an instance or a version of the software application, generate a similarity value for the stored user context based on comparing the current user context to the stored user context, wherein the similarity value indicates a degree of similarity between the first flow of operations and the second flow of operations, and transmit the similarity value to the resource engine.