A network manager establishes a network connection with a local area network (LAN) using a gateway device that interfaces the LAN with the Internet. A request is transmitted to the gateway device via the network connection to access a Web server of the Internet. A response page received from the Internet via the gateway device is examined to determine whether the response page is a redirect page, or if the response page is from a domain different from that was requested, from a Web proxy server that requires a user to log in, in order to access the Web server. It is determined whether credentials associated with the user required for the login page have been previously cached locally. The cached credentials of the user is automatically provided in response to the redirect page without user intervention to log into the Web proxy server, if it is determined that the credentials have been previously cached locally.