Servlets within a web server maintain state information concerning requests made by users of the server. The servlets associate each user with an HTTP session object. The session object is configured to include information that identifies the last-N web pages requested by the user. Periodically, or in response to a triggering event, the server analyzes the contents of the session objects, for example by tabulating the frequency with which each web page has been requested in the recent past. From the results of the analysis, web-page caching priorities are determined, and the contents of the server's cache are altered accordingly.