This disclosure describes an automated process of discovering characteristics needed to integrate a web-based application to a web portal, such as a reverse proxy. This process eliminates the need for application owners and security analysts to manually discover the information needed for the on-boarding process. To this end, application-specific information is determined by monitoring network traffic flows in and out of the application, user authentication and authorization event data, and the like. An application discovery engine analyzes the discovered data, preferably against a set of patterns and heuristic-based rules, to discover or identify the one or more application characteristics. A set of configuration data is then generated, and this configuration data is then used to integrate the application into the web reverse proxy and, in particular, by specifying the configuration needed to “board” the application. Preferably, the monitoring and application characterization determination functions occur in an automated manner.