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johnny181 asked on

Outlook 2010 windows security pop-up

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
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johnny181

8/22/2022 - Mon
Simon Butler (Sembee)

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?

Simon.
ASKER
johnny181

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.
Simon Butler (Sembee)

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.

http://semb.ee/hostnames

Simon.
Experts Exchange has (a) saved my job multiple times, (b) saved me hours, days, and even weeks of work, and often (c) makes me look like a superhero! This place is MAGIC!
Walt Forbes
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johnny181

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johnny181

resolved myself