Outlook Security Alert for Someone Else's Certificate Problem

Posted on 2013-10-25
Last Modified: 2013-10-30
When I open Outlook 2013 on my Windows 8 Pro computer and open my Exchange 2010SP2 mailbox, I get a security alert for the domain "".  The problem is that this is not a server in my domain.  My server is "".  I select "No" to the alert and Outlook works flawlessly.  The Exchange Connectivity Analyzer does not report any problems.  I have tried deleting and recreating my Outlook profile, deleting/recreating/reinstalling server certificate, another version of Outlook, different computers with XP and 7, and connected to different networks with different ISPs and DNS servers.  I don't get this message when I use OWA.

What is causing this alert and how to I get rid of it?

Thank you in advance!
(Note: I have replaced the actual server names with fakes that follow the same format for security purposes.)
Question by:ADMlNlSTRATOR
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LVL 15

Expert Comment

ID: 39602972
What's the exact error message that you're getting?

Do you have a email in your inbox from someone in the domain (the server name that you're getting the alert about)?

Are you using autodiscover or have you specified your server name manually?  Do other people in this domain get the same warning?

It sounds like either:
1) There's an error in the autodiscover xml or
2) There's a signed message in your inbox that is invalid - though with this, I'd expect the warning only once.

Author Comment

ID: 39607263
Thank you for your comment!

Pop up window says "Security Information you exchange with this site cannot be viewed or changed by others. However, there is a problem with the site's security certificate.  Etc.  The rest of the message is not important because it is not my domain and I don't care if this certificate is good or not.
I don't have, or ever had, emails from this domain in my mailbox.
I am using autodiscover and other people in the domain also get this securit alert.

Please keep the comments coming, I am sure the answer is out there somewhere.
LVL 15

Expert Comment

ID: 39607731
I bet the exchange server is setup wrong.  

I know the domains you gave are only examples, but one wrong one (the one that shows in the alert) really the same as your real domain except it's missing the first word?  (for example, your domain is and the warning is about without the north?)

If so, I'm guessing that the exchange administrator setup autodiscover wrong and inadvertently left off the North part.  Could it be that the non-north domain is a cname to your valid mail server?  That would make sense as to why it's still woring, but with a warning since the certificate includes the North.

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Author Comment

ID: 39609058
Thank you for your comment.
The answer to your first question is, "Yes".
The answer to your second question is, "No".
Please take the time to read my comments and the comments of others before commenting again.  I already stated that I tested Exchange connectivity.
I will add that the wrong domain is not listed in the Exchange server's DNS, Autodiscover.XML or the public DNS.

Still looking for a solution...
LVL 15

Expert Comment

ID: 39609115
First, I'm so terribly sorry for recommending that you check the MS connectivity test tool.  I fully read your original post, but did no re-read it after you replied to my questions after 2 days, and forgot that you mentioned this one simple (but important) test.  I read lots of posts here in an attempt to help.  I know that you've paid for your membership, but please remember that we are all completely unpaid volunteers here.

If everyone who is using the Exchange server is getting this error, it's got to be something with the configuration - it's going to be a human error in not adding the "North" part of the server name.

Are you the server admin?  Can you run powershell commands on the server to look at the configs?

Author Comment

ID: 39609198
Thank you for understanding my concern weinberk.
I built the Exchange server and I am the sole administrator.
Please let me know what commands I should run.
LVL 15

Accepted Solution

weinberk earned 500 total points
ID: 39609740
Lets start with this:
Get-WebServicesVirtualDirectory |fl identity,internalurl,externalurl

and this:
Get-ClientAccessServer |fl identity,autodiscoverserviceinternaluri

Post the results (redacted)

Author Comment

ID: 39613171
The first command lists the wrong server name under "ExternalURL".
I used the "Set-webservicesvirtualdirectory" command to change it to the correct server.
I restarted the server but the security alert persisted.
I flushed DNS and recreated my Outlook profile and I haven't see the alert yet.

It looks pretty cut and dry.  I made a typo and found it with your help.

You are truly an expert.

Please let me know if you have any idea why ECA did not detect this problem.
LVL 15

Expert Comment

ID: 39613219
Glad to have helped.  Some time all it takes is another set of eyes.  

I've got no idea why MS's tool didn't detect the error.  You'd sure think it would.  

Wouldn't the XML for autodiscover show the wrong info too.

In any case, I'm glad I helped you get this sorted.

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