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I have a question about windows servers and proxies. I'm the web person for a large hospital and our IT team can't solve an issue involving our domain name.

We recently moved our web hosting server from an internal machine to a leased, external, dedicated server at my recommendation (our I.T. people couldn't even get us a proper database running on the internal one).

Any computer connected to our internal network has a setting in their internet explorer that says if they are visiting *.ourdomain.com then do not redirect them through the proxy server and just send them to the proper server in our network. This is all good, except we need www.ourdomain.com to point to the new web server and it should go through the proxy. Well, we have about 15 or 20 subdomains and the I.T. people say they'd prefer not to list them all out in the i.e. exceptions because it'd require too much work to manage (wtf?).

So, is there any other solution? Right now what I've done is put a redirect isapi filter in IIS on the internal web host and any request is rewritten as replace www.ourdomain.com with www.ourOtherdomain.com which is confusing a ton of people. We don't want visitors hitting ourOtherdomain.com.

Any advice or firepower for my meeting with I.T. tomorrow would be awesome.

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Why do you want to be proxying your externally hosted domain? I can see that it may save bandwidth, but people updating pages will experience weird issues related to caching. – Zoredache Aug 11 '10 at 19:51
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3 Answers

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Any computer connected to our internal network has a setting in their internet explorer that says if they are visiting *.ourdomain.com

If I understand your question correctly the majority of your servers on your domain exist on your internal network and you do not want to proxy those, but you do want to proxy the externally hosted servers.

One way to do this may be to simply remove the *.ourdomain.com exception and instead add exceptions based on your internal address space. So if you where using private addresses inside your network you might add an exception like this 10.0.0.0/8, 172.16.0.0/12, 192.168.0.0/16. Of course you would just use the network or networks that is actually being used.

You might suggest to your IT guys to also consider setting up WPAD this technology allows you to specify the exceptions and proxy configuration in a single javascript file hosted somewhere on your network. I find that a WPAD configuration is far easier to maintain then the a group policy exception list. WPAD is supported by most browsers, although you do have to enable it on Firefox.

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Are you actually using a .com - if you're a uk based hospital and have a .nhs.uk based domain the rules for subdomains become a bit tricky because of the odd way connecting for health administer the domains.

I don't see why they couldn't use a logon script... and also take a look at this thread on neowin

http://www.neowin.net/forum/topic/631024-global-proxy-setup-for-windows-vista/

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it's a us, .com domain, checking out that article now – Chris Flannagan Aug 11 '10 at 19:49
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What about using DNS to catch internal requests and forward them to the appropriate location?

i.e. requests for internal.foo.com are forwarded to new.internal.foo.com

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That's what a couple people have recommended, but one fella said this would be an issue with doing that: it doesn't look like "Bypass proxy server for local addresses" will solve your problem in this case, since that setting applies to hostnames. In the Windows XP/7 proxy settings, any FQDN or IP address (anything with dots in it) gets sent to the proxy, even if it's on the LAN, unless an explicit exception is specified support.microsoft.com/kb/262981 – Chris Flannagan Aug 11 '10 at 19:50
Why does your organization need to run the new web server through the proxy, or rather without the proxy? It would seem that if you are going outside the organization you would want to treat it as any other web site when viewing. – Chris Aug 11 '10 at 19:55
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