A method of enabling persistent access by a Web server to files stored in a distributed file system of a distributed computing environment that includes a security service. A session manager is used to perform a proxy login to the security service on behalf of the Web server. Persistent operation of the session manager is ensured by periodically spawning new instances of the session manager process. Each new instance preferably initializes itself against a binding file. A prior instance of the session manager is maintained in an active state for at least a period of time during which the new instance of the session manager initializes itself. Upon receipt of a given transaction request from a Web client to the Web server, a determination is made regarding whether a new instance of the session manager process has been spawned while the Web server was otherwise idle. If so, the Web server is re-bound to the new instance of the session manager process so that the new instance of the session manager process can respond to the transaction request.