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Random request for login using Outlook

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Using a self signed cert for SBS Server adn exxchange email with Small Business Server 2008.  IT guys installed new cert and mail and everything works fine it's just every desktop randomly asks for us to login

Message is To use Micorsoft Office Outlook with your Microsoft Exchange Server you must provide a password. Click here to type password.

Outlook seems to be working fine but constantly getting prompted is annoying


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