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Outlook 2010 Error - "There is a problem with the proxy server's security certificate" - Error Code 10

    Frage

  • Hello,

    I am receiving the following error message from time-to-time in Outlook 2010 on two different client machines....

    "There is a problem with the proxy server's security certificate.  The name on the security certificate is invalid or does not match the name of the target site name.  Outlook is unable to connect to the proxy server. (Error Code 10)."

    These machines connect to an Exchange 2003 server over RPC/HTTPS (Outlook Anywhere) across the Internet using a self-signed certificate.  The client PCs have the self-signed certificate imported into the trusted root certificate authority certificate stores for computer and user accounts.  The self-signed certificate has not expired.  Oddly, this error message appears from time-to-time disruputing communication with Outlook, but after a few minutes, communication will start working again before the error mesage is thrown.  This just started happening recently, and to much knowledge, the users did not receive this error message prior. 

    Has anyone experienced a similar issue?  What is mind-boggling is that Outlook does not have total communication failure...just intermittent issues with an obnoxious error message.  My theory is that a recent update or patch could be to blame as it is the only thing that I could possibly think of that has "changed" on both of these PCs with Outlook.  Anything else that I have found on this forum and on the Internet suggests total communication problems because of issues with the certificate.  However, this is a similar error message but with different problems and symptoms.  Any help and/or suggestions would be much appreciated!

    Thank you,

    Jim

    Donnerstag, 26. Mai 2011 15:27

Antworten

  • Hi

    At the OL2010 profile, do you have the value msstd value populated (At the "Microsoft Exchange Proxy settings" tab)

    if yes, is that the same string which is present at the "issued-to" of your certificate?

    If not, can you change this msstd:<string> to match the issued-to value of your IIS\E2k3 servers certificate

    Cheers

    Asri

    Donnerstag, 26. Mai 2011 15:41

Alle Antworten

  • Hi

    At the OL2010 profile, do you have the value msstd value populated (At the "Microsoft Exchange Proxy settings" tab)

    if yes, is that the same string which is present at the "issued-to" of your certificate?

    If not, can you change this msstd:<string> to match the issued-to value of your IIS\E2k3 servers certificate

    Cheers

    Asri

    Donnerstag, 26. Mai 2011 15:41
  • Asri,

    Thank you.

    Jim

    Donnerstag, 26. Mai 2011 19:49
  • Hello,

     

    Yes, the most possible causes is the certificate principal name. You can also try setting it to null by the following command to workaround this issue.

     

    Set-OutlookProvider -Identity EXPR -CertPrincipalName $null

     

    Thanks,

    Simon

     

    • Als Antwort vorgeschlagen RichardTapps Montag, 1. August 2011 04:22
    Montag, 30. Mai 2011 03:04
  • Hi Jim,

     

    I just fixed the same problem...  You also need to make sure you install the self signed certificate in the correct folder (trusted Certificates)

     

    Cheers

    Richard

     

    Montag, 1. August 2011 04:23
  • Thanks Asri... I am able to resolve the issue.
    Dienstag, 23. August 2011 05:49
  • Hi,

    I am in the same situation.

    Certificate MisMatch OR Outlook .... proxy server...Error 8, works fine when connect through VPN or internal LAN. IMAP & POP is working fine.

    Exchange Test says the same thing.

    The site has SBS 2011, Exchange 2010, Outlook 2010 external client and NO Public SSL yet.

    I realised there is no entry for Autodiscover.EXTERNALDOMAIN.NAME (e.g. autodiscover.contso.com) on the certificate. How would I add a domain to current certificate?

    Strangly, outlook is pulling all the information from Server.

    Any experience ?????


    Mittwoch, 12. September 2012 11:31
  • Hi sharpwaves

    You will have to reissue the certificate with the correct entries added to it. This may mean buying a new one, adding it in at renewal or creating a new self signed with the correct entries. 

    Hope this helps

    Montag, 22. Juli 2013 13:49