The disclosed embodiments are directed toward monitoring and classifying encrypted network traffic. In one embodiment, a method is disclosed comprising intercepting an encrypted network request, the network request transmitted by a client device to a network endpoint; identifying a network service associated with the network endpoint based on unencrypted properties of the encrypted network request; identifying, based on the encrypted network request and a series of subsequent network requests issued by the client device, an action taken by the client device, the action comprising an activity performed during a session established with the network service; and updating a catalog of network interactions using the network service and the action.