Making Proxy Server Work in a Windows 2000 Environment

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I recently made a decision to relocate my business to another state. During the process of planning the relocation, I realized that the type of Internet connection that I have now won’t be available in my new location. Presently, I am using a DSL connection. This connection comes into a DSL router. The router is then connected to one of the network cards on my Proxy Server through a standard CAT 5 cable.

As I was investigating the Internet connection possibilities in my new location, I realized that the only broadband connection available to me was through the use of a satellite modem. Unfortunately, rather than connecting to a network card the way that my DSL router did, the satellite modem connects to a USB port. The problem with this is that Proxy Server is designed to run on Windows NT, and Windows NT doesn’t support USB devices.

I realized that I was going to have to make some changes before I would be able to distribute my Internet connection to my other computers. The only real feasible options all involved upgrading to Windows 2000 because of Windows NT’s inability to interact with USB devices. My options were to use Windows 2000’s Internet Connection Sharing Service (ICS), use ISA Server, or figure out a way to make Proxy Server work under Windows 2000.

I decided to try to make Proxy Server work under Windows 2000 because ICS is less secure than Proxy Server, and with the move coming up so quickly, I didn’t have time to learn ICS. However, making Proxy Server run under Windows 2000 was easier than I ever expected.

I began the process by performing a full system backup of the server by using Symantec’s Ghost 2001. This utility allowed me to create an image file on a CD. I could use the image file to quickly restore the entire PC if something went wrong. I ran into some problems while creating the image CD though. Some of the long filenames in the proxy cache kept causing Ghost 2001 to crash. I got around this problem by manually emptying the cache directories. 1 GB and 75,000 files later I was able to successfully make a ghost image of the server.

Once I created a full systems backup, I decided to backup the Proxy Server Settings. To do so, go into the IIS Console and navigate through the console to Internet Information Server | your server | Web Proxy. Now right click on Web Proxy and select the Properties command from the resulting context menu. When you see the Web Proxy Service Properties sheet, you can use the Server Backup button on the Service tab to back up the Proxy Server’s configuration. If you have other types of proxies set up, such as a Winsock Proxy, you may have to back them up by using the same procedure.

Once I had a backup, I upgraded Windows NT to Windows 2000. As expected, I received a message stating that Proxy Server 2.0 wouldn’t run under Windows 2000. I ignored the message and continued the upgrade. When the upgrade completed, I downloaded a utility from the Microsoft Web site to allow you to run Proxy Server 2.0 on Windows 2000. You can find the utility at

After downloading the utility, insert your Proxy Server CD into the CD-ROM drive and run the utility. The utility will run the Proxy Server setup program and install Proxy Server onto your system. When I used this utility, I lost all of my Proxy Server settings. Therefore, I simply restored my Proxy Server backup by using the Server Restore button on the Web Proxy Service Properties sheet’s Service tab.

Once I restored all of my settings, the Proxy Server was back up and running. I didn’t have to make any changes to my clients, and there have been no noticeable problems since the upgrade.

Brien M. Posey is an MCSE who works as a freelance writer. His past experience includes working as the director of information systems for a national chain of health care facilities and as a network engineer for the Department of Defense. Because of the extremely high volume of e-mail that Brien receives, it’s impossible for him to respond to every message, although he does read them all.

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