A method includes, for each of a plurality of web resources, receiving, at a communications server, data indicating characteristics of a respective web resource, detecting, based on the received data, that the respective web resource provides functionality for live assistance by a third party content provider through a chat user interface on the respective web resource, and storing, in a database, an entry that indicates that the respective web resource has the functionality. The method includes receiving, from a user, a request to access a particular web resource hosted by a particular third party content provider, determining, based on a stored entry in the database representing the particular web resource, that the web resource provides functionality for live assistance by the particular third party content provider through a particular chat user interface on the web resource, and initiating a chat session between the user and the third party content provider.