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By the way, I've tried simple things like rebooting on one of the machines. I didn't want to reboot the other because we would lose all access to our web based utilities and one operational machine is better than none. I'm slowly trying to educate myself on Windows 2000 networking, but it's difficult to research this problem and perform my other duties. After some study, I thought it might be a problem with DNS caching, but an "ipconfig /flushdns" did not resolve the problem. I've also tried swapping connections with other clients that are not experiencing problems, no difference. It seems to be exclusive to Windows 2000. Has anyone experienced this problem?

total shot in the dark, check connection settings under tools, internet options, specifically the lan button on the lower right hand side. Is there a proxy server somewhere in the mix? Also, maybe upload to latest version of I.E.

This may be impossible to diagnose over the web. Try some of these things.

Pick a web site, any web site, determine its IP address by pinging the website name, create a host file on the W2K machine for that web site. When you cannot access the web try that specific web site with the browser. If it loads then your DNS provider is having problems. If it does not respond then you need to look internally first. I am a Cisco person and don't know anything about Cayman routers, but if it were me I would buy a small 4 port switch then connect the router to one port and the two PC's to two other ports. Check your network cards and cables to make sure they are OK. If you get too much errors/collisions/noise this could be causing your problem.

Do you have any type of Access Control Lists set up or other types of packet filtering, usage policy, or security in place that could be causing this?

Do you know for sure that you actually have internet connectitivy when this happens? Is any other type of traffic going across your DSL connection?