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Outlook Security Warning

Posted on 2011-02-14
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Last Modified: 2012-05-11
I am having a problem with users running Outlook 2007 and trying to send email though Port 587 using TLS.  I think the problem is on the server.  In the Exchange Shell screenshot below you will see the CN name as "SERVER" and then you will see the correct CN name below it.  If you look at the details of the error that Outlook is giving, you will see the "Issued To" also states "SERVER" but should be the FQDN.  Any suggestions on what looks wrong here?  Thanks. Certificate CN from Exchange ShellOutlook-Cert-Error-Message.gif
Certificate-Error---Wrong-CN-Nam.gif
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Question by:gruen33
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by:Suliman Abu Kharroub
ID: 34892699
from MMC, copy this certificate from personal store to trusted root certificates.
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Author Comment

by:gruen33
ID: 34893626
Thanks Suliman.  I tried copying both items to the Trusted Root Certification Authorities >Certificates folder.  Still having the same issue.  I am attaching a screenshot of the MMC.  Please let me know if you have any other ideas.  Thanks. MMC Screenshot with Cert Info
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by:Suliman Abu Kharroub
ID: 34901998
From EMC, go to server configurations and from action panel use the "assign services to certificate" wizard to assigned the correct certificate (Godaddy) to outlook anywhere ( rpc/https) service.
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Author Comment

by:gruen33
ID: 34907863
SulimanW, I do not see that option in Exchange 2007.  I have researched that option and I see where that is done in 2010.  Any thought on how to do this in 2007?  Thanks, it appears we may be on the right track.
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by:Suliman Abu Kharroub
ID: 34908692
In exchange 2007, you can do it using powershell:

Enable-ExchangeCertificate -Services:"SMTP" -thumprint "thumprint"

where services one of these values :Pop,SMTP,IIS, IMAP, None, federation.

You can find the thumprint from certificate details. but make sure to remove spaces.
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by:Suliman Abu Kharroub
ID: 34908709
also "Get-ExchangeCertificate" will show you thumprints.
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Author Comment

by:gruen33
ID: 34911591
Thanks.  I did do this and was asked if I wanted to overwrite the Existing Default SMTP Certificate and I chose YES.  I am assuming that the S under Services refers to SMTP.  The old valude still exists along with the new value.  Below is a screenshot.  How do I remove the old Thumbprint that shows CN=SERVER?  Thanks- screenshot-1
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by:Suliman Abu Kharroub
ID: 34911623
You can safely delete the certificate, but as backup just export it from MMC console to somewhere safe. then delete it. You may need to restart exchange services.
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Author Comment

by:gruen33
ID: 34913286
Well that error is gone but I have a new one.  Outlook is configured for SMTP Port 587 with TLS.  The error is in the screenshot when testing the send functionality.  Thanks, I really appreciate you helping me out on this. New test send error using TLS
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by:Suliman Abu Kharroub
ID: 34913888
Do you have latest updates installed on outlook and exchange ?
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Author Comment

by:gruen33
ID: 34916553
I performed the steps you gave above by exporting the Certificate that had the Thumbprint associated with CN=SERVER and then deleting it via MMC.  I restarted the server and now there is only one certificate showing up in MMC which should be correct.  OWA Certificate works just fine, still not working with SMTP.  Is there a method where I have to "Bind" it somewhere, like to the local IP address.  Yes, all updates are current for both Exchange 2007 and Outlook 2007.  Below is a screenshot of the Cert via Shell.  Thanks- Cert Screenshot After Removing CN=SERVER Thumbprint
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Author Comment

by:gruen33
ID: 34920342
FYI:  I can send just fine with encryption setting as "None".  I would rather not do that though.
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Accepted Solution

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Suliman Abu Kharroub earned 500 total points
ID: 34922544
please try again:  "Enable-ExchangeCertificate -Services:"SMTP" -thumprint "thumprint""

If that does not work please refer to "Client to Server Secure SMTP Connectivity in Exchange Server 2007" :http://www.shudnow.net/2008/02/10/client-to-server-secure-smtp-connectivity-in-exchange-server-2007/
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Author Comment

by:gruen33
ID: 34923442
Thanks, I read that.  Still no luck.  It doesn't make sense that I can send using Port 587 using authentication without TLS or SSL selected.  Testing with either TLS or SSL seleced gives me the error I posted earlier "Your server does not support the connection encryption type you have specified".  I'm stumped.  I will keep researching.  If you come up with another idea please let me know.  Thanks for all the work you have put into this for me.
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by:Suliman Abu Kharroub
Suliman Abu Kharroub earned 500 total points
ID: 34926552
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Assisted Solution

by:gruen33
gruen33 earned 0 total points
ID: 34931578
OK, it actually ended up being something simple.  I went into MMC and into the properties of GoDaddy Class 2 Certificate Authority and selected "Enable All Purposes for this Certificate".  I am not sure why it was not selected but that did the trick.  Thanks for all your help and direction. MMC where i changed the properties
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Expert Comment

by:Suliman Abu Kharroub
ID: 34932919
Glad to hear that..
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Author Closing Comment

by:gruen33
ID: 34959296
Sulimanw pointed me in the right direction on serveral responses.  After digging a bit while using his responses I was able to find the solution.
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