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Outlook 2010 fails login to POP3/SMTP services on Server 2003

Posted on 2010-11-16
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I have a windows 2003 server that I originally put online in 1999 for self education and to host my own website and email (POP3 and SMTP) services. I now provide the same services for half a dozen clients with individual domains. One client has just attempted to upgrade to Outlook 2010 and called for help when attempts to login failed. It appears that the problem occurs because Outlook 2010 uses the CAPA command in place of the AUTH command in its connection string.
Following are network traces that provide more information:

From Outlook 2010 making a connection attempt . . .
449   3.055000  MXSERVER   MXCLIENT   POP3   POP3:Response: +OK: Microsoft Windows POP3 Service Version 1.0 <846424703@banshee.corp.technologytoolbox.com> ready.
450   3.055000  MXCLIENT    MXSERVER  POP3   POP3:Command: CAPA
451   3.056000  MXSERVER   MXCLIENT   POP3   POP3:Response: -ERR, Error: Unacceptable command
452   3.056000  MXCLIENT    MXSERVER  POP3   POP3:Command: QUIT

From Outlook 2007 making a connection attempt . . .
2225   15.118164   MXSERVER   MXCLIENT   POP3   POP3:Response: +OK: Microsoft Windows POP3 Service Version 1.0 <846956359@banshee.corp.technologytoolbox.com> ready.
2229   15.210937   MXCLIENT    MXSERVER   POP3    POP3:Command: AUTH  
2230   15.212890   MXSERVER   MXCLIENT    POP3    POP3:Response: +OK
2231   15.241211   MXCLIENT    MXSERVER    POP3   POP3:Command: AUTH  NTLM
2232   15.243164   MXSERVER   MXCLIENT    POP3    POP3:Response: +OK

I am looking for a workaround to this problem. Can either Outlook or Server 2003 be configured to accommodate the other? Failing to find a workaround I may have to upgrade the services. I would welcome suggestions regarding alternatives.
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Question by:KWHenderson
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DrUltima earned 250 total points
ID: 34164676
Some routers drop the CAPA packets, and this causes Outlook 2010 to fail to connect.  What type of router do you have?  Unfortunately, the only solution to this I have found is to have the router not inspect POP3 packets.  Several Cisco routers see CAPA as invalid on POP3 traffic.  You are not alone in your error:

http://blogs.msdn.com/b/jjameson/archive/2010/04/26/outlook-2010-does-not-work-with-windows-server-2003-pop3-service.aspx

http://grantnz.blogspot.com/2010/07/outlook-2010-fails-to-retrieve-mail.html

Alternately, I am not sure that Server 2003 POP services even support CAPA, and if that is the case, even if your router was passing the traffic, it would still not work because the server doesn't know what to do with the request.

If you must use 2010 on mail from Server 2003, you need to use SSL or IMAP, not straight POP3.  Your alternative is to get a different mail client or a different mail server.
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by:KWHenderson
ID: 34164977
Hello DrUltima;

  Thank you for respoinding. I had reveiwed the information at the links you provided prior to submitting to the Experts Exchange. In fact, the Jeremy Jameson page is where I found the network traces in my original posting. You have presented what I need to make a decision. I will move along to SSL or not support Outlook 2010.
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