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NTLM Authentication Issues for External users with domain machines

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We have decided to change our Exchange Servers from FBA to Windows Authentication. However, we have identified an issue with our setup which is causing issues

We currently have a url for webmail, which is https://myserver.mydomain.co.uk/owa. The Certificate is *.mydomain.co.uk, and is signed by a third party

Internally, we used Trusted sites to Automatically authenticate with SSL secured systems on the network in order to allow users access to remote apps using our terminal servers, and this extends to the mail servers, as this is global for internal servers. This all works perfectly, and everyone is happy

Until they get a laptop

Laptop users, when out of the office, physcially cannot access Webmail through Internet Explorer. When attempting to access webmail on IE from any machine with a set of valid Windows Credentials, a "Page Cannot be Displayed" error is presented. When the site is untrusted, the credentials can be entered and passed throuh correctly, but automatically this just fails.
Can anyone provide some assistance as to why this might be?



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