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I have links contained in Outlook (tested in 2007 and 2010) mail messages that point to internal websites hosted by IIS. They require windows authentication to be accessed. When someone opens one of these links Internet Explorer displays the generic "Internet Explorer cannot display the webpage" error. If the user hits refresh, IE displays the windows authentication dialog as expected.

This occurs in both Windows 7 (IE 9) as well as Windows XP (IE 8).

Here are a few things I have learned so far: These websites are on a different domain, but are still on our private network and require windows authentication. Because the sites are on a different domain, Internet Explorer does not automatically open them in the Local intranet zone. If I add the URL of these sites to the local intranet zone the problem goes away.

I have also noticed a significant difference between the request being sent when the URL is in the intranet zone versus when it is not:

When the URL is in the Internet zone the initial request contains this:

Accept: text/html, application/xhtml+xml, */*
User-Agent: Mozilla/5.0 (compatible; MSIE 9.0; Windows NT 6.1; WOW64; Trident/5.0)

When the URL is in the Local intranet zone the initial request contains this:

Accept: */*
User-Agent: Mozilla/4.0 (compatible; MSIE 7.0; Windows NT 6.1; WOW64; Trident/5.0; SLCC2; .NET CLR 2.0.50727; .NET CLR 3.5.30729; .NET CLR 3.0.30729; Media Center PC 6.0; .NET4.0C; InfoPath.3; .NET4.0E)

Does anyone know what is causing this issue?

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Have you excluded DNS timeout as a possible cause? –  user3463 May 17 '12 at 22:01
    
I haven't tested for it exactly, but the error is shown instantly. If it were a DNS issue wouldn't it remedy itself the first time the site was accessed (upon hitting refresh)? Wouldn't it also impact non-authentication required sites? –  ddechant May 19 '12 at 0:05
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