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IIS site that uses Windows Auth doesn't prompt for credentials from outside

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We have a staff portal site on IIS with Windows Authentication for SSO, when accessed externally on work machines the site is inaccessible and returns 'this page cannot be displayed' a fiddler check show it getting a 401 Unauthorized error.

On non work machines like home pcs it prompts for the user credentials and then works fines.

I believe the problem is caused by the fact that this site is added to a IE security zone that has 'automatic logon with current user name and password' enabled.

But it should just prompt if it can't login.


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