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There are loads of reasons for the authentication prompt, the most common being an issue with the SSL certificate. Do you have a trusted SSL certificate on the server? Does the name on it resolve internally correctly and is Exchange configured to use it?<br />
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Simon.
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we purchased (renewed) the certificate from RapidSSL back in 2012. How do I check to see if it resolves internally correctly? Like I said, nothing has changed other than doing windows updates and the exchange updates.
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RapidSSL don't sell UC type certificates, so you must have it for your external host name only. Therefore you need to check that the common name on the certificate resolves internally. If it does not, then setup a split DNS system and configure Exchange to use the external host name internally.<br />
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<a href="http://semb.ee/hostnames" rel="ugc">http://semb.ee/hostnames</a><br />
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Simon.
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I just upgraded our Exchange 2010 server to the latest version, service pack 3 roll up 5. Since that upgrade, a few users (out of 40, maybe 5) are getting the security pop up. We have a terminal server running and I was just told (and confirmed) that it is also happening on that system. We run Windows 2008 R2 servers. <br />
The exchange server upgrade is the only thing that has changed.<br />
I've gone through the settings on the Exchange server (EMC) but everything looks fine there. Since it was working fine before &nbsp;the upgrades, I'm really not sure what to look for at this time
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I just upgraded our Exchange 2010 server to the latest version, service pack 3 roll up 5. Since that upgrade, a few users (out of 40, maybe 5) are getting the security pop up. We have a terminal server running and I was just told (and confirmed) that it is also happening on that system. We run Windows 2008 R2 servers. 
The exchange server upgrade is the only thing that has changed.
I've gone through the settings on the Exchange server (EMC) but everything looks fine there. Since it was working fine before  the upgrades, I'm really not sure what to look for at this time

Outlook 2010 windows security pop-up

Exchange is the server side of a collaborative application product that is part of the Microsoft Server infrastructure. Exchange's major features include email, calendaring, contacts and tasks, support for mobile and web-based access to information, and support for data storage.

Exchange

Microsoft Outlook is a personal information manager from Microsoft, available as a part of the Microsoft Office suite. Although often used mainly as an email application, it also includes a calendar, task manager, contact manager, note-taker, journal, and web browser.