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Why can't I receive email after renewing my MS Exchange 2007 server SSL certificate?

Posted on 2015-01-15
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Last Modified: 2015-05-24
We renewed the SSL Certificate on our MS Exchange Server 2007.  Users using MS Exchange with MS Outlook 2007/2010 kept working fine.  Users using MS Outlook 2007/2010 with POP3 stopped receiving email.

We were forced to renew the certificate with new hash strength, from SHA1 to SHA2.

1.  We checked our firewall.  No changes made.

The only change was to replace the SSL certificate on the email server.  We verified that POP was assigned as a service to the certificate thumbprint.

Any thoughts?  SHA2 issue???

Luis Mendoza
(Net Admin)
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Question by:Luis Mendoza
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11 Comments
 
LVL 30

Expert Comment

by:Sudeep Sharma
ID: 40551687
Which client are you using for POP3 download?

Did you tried Microsoft Remote Connectivity Analyzer for POP3 emails, is that reporting it fine?

Remote Connectivity Analyzer
https://testconnectivity.microsoft.com/

Thanks,
Sudeep
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LVL 33

Expert Comment

by:Dave Howe
ID: 40551951
Could be an schannel version issue - what OS are you running outlook on?
0
 

Author Comment

by:Luis Mendoza
ID: 40551978
Sudeep,
  We are using MS Outlook 2007/2010 to download email.  We use webmail as well which works fine.  We are trying the analyzer now.

Any other ideas are welcome.  thanks,

Luis
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Author Comment

by:Luis Mendoza
ID: 40551998
Dave,
  We are running MS Windows 7 32/64 bit, Pro and Ultimate.

thanks
Luis
0
 
LVL 33

Expert Comment

by:Dave Howe
ID: 40552008
That should be fine then. Win7/8 Schannel supports the newer protocol suites.
I would normally try wireshark next - capture an attempted login and see if there are any issues setting up TLS.
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LVL 30

Expert Comment

by:Sudeep Sharma
ID: 40552010
Give a other email client like Thuderbird a try if that connects, so that we know that the issue is related to Outlook and not Exchange.

Thanks,
Sudeep
0
 

Author Comment

by:Luis Mendoza
ID: 40552023
1.  Will try Wireshark and see what it can tell us

2.  Will look into Thunderbird as well


thanks!
Luis
0
 

Author Comment

by:Luis Mendoza
ID: 40552116
By the way we are getting a general error on MS Outlook but here it is:

"Task "username" - Receiving' reported error (0x800CCC0F) : 'The connection to the server was interrupted.  If this problem continues, contact your server administrator or Internet service provider (ISP).'
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Accepted Solution

by:
Luis Mendoza earned 0 total points
ID: 40628633
We resolved the issue of not passing POP by by creating a new SSL certificate request, resubmitting to the CA/certificate provider, and then re-importing the certificate into the mail server (also, assigned all the services that we wanted the certificate to support.).

This seem to have been a corrupted certificate.  However, we now have an issue with passing secure POP.  It does not seem to support passing secure POP.
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Author Comment

by:Luis Mendoza
ID: 40785551
No objections
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Author Closing Comment

by:Luis Mendoza
ID: 40793674
This resolved not being able to pass standard POP email, however did not allow us to pass encrypted email.  I am posting a separate question for that issue.
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