How can I configure the Microsoft Proxy Sserver to automatically dial out to the ISP when needed?

From the Start menu, select Settings, Control Panel, then Services to start the Services Control Panel applet.

Select Remote Access Autodial Manager, and click Startup.

Select the Disabled setting, and click OK.

Select Remote Access Connection Manager, and click Startup.

Select the Automatic setting, and click OK.

Close the Services Control Panel applet.

Select Start, Settings, Control Panel, Network, then the Network Control Panel, or right click Network Neighborhood and select Properties.

Select the Bindings tab.

Select Show Bindings for all adapters.

You might have several Remote Access WAN Wrappers. Expand each one, and if you see WINS Client(TCP/IP), select it and click Disable.

Click OK.

Your OS will update your machine’s bindings, and you should click Yes to restart your computer.

Select Start, Programs, Microsoft Proxy Server, then ISM.

Double click a computer name next to either the Socks, Winsock, or Web proxy service.

Click the Auto Dial button.

Select the Configuration tab, and check Enable dialing for Winsock and SOCKS proxy if you want the server to automatically dial for either service. Check Enable dialing for Web proxy primary route if you want dialing for the Web proxy service.

You can also choose a specified timeframe during which the autodial is valid.
Note: The connection will not hang up during unspecified hours, but Proxy Server won’t initiate a new connection.

Click the Credentials tab.

Select the Phonebook entry and the required username and password details. I would advise you to create a connection script if you need to enter logon information in a terminal window during the connection (see Q. How can I create a RAS Connection Script?).

Click Apply, then OK.