?
Solved

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

Posted on 2010-11-16
2
Medium Priority
?
2,196 Views
Last Modified: 2012-05-10
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.
0
Comment
Question by:KWHenderson
[X]
Welcome to Experts Exchange

Add your voice to the tech community where 5M+ people just like you are talking about what matters.

  • Help others & share knowledge
  • Earn cash & points
  • Learn & ask questions
2 Comments
 
LVL 31

Accepted Solution

by:
Justin Owens earned 1000 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.
0
 

Author Comment

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.
0

Featured Post

Get your Disaster Recovery as a Service basics

Disaster Recovery as a Service is one go-to solution that revolutionizes DR planning. Implementing DRaaS could be an efficient process, easily accessible to non-DR experts. Learn about monitoring, testing, executing failovers and failbacks to ensure a "healthy" DR environment.

Question has a verified solution.

If you are experiencing a similar issue, please ask a related question

Many people use more than one email account and so it becomes difficult for them to manage them when they use separate accounts,  so, in this article, I have shared an easy way to add Other Mail Accounts in your Google Inbox. It helps to combine all…
This article will help to fix the below error for MS Exchange server 2010 I. Out Of office not working II. Certificate error "name on the security certificate is invalid or does not match the name of the site" III. Make Internal URLs and External…
This Experts Exchange video Micro Tutorial shows how to tell Microsoft Office that a word is NOT spelled correctly. Microsoft Office has a built-in, main dictionary that is shared by Office apps, including Excel, Outlook, PowerPoint, and Word. When …
To add imagery to an HTML email signature, you have two options available to you. You can either add a logo/image by embedding it directly into the signature or hosting it externally and linking to it. The vast majority of email clients display l…
Suggested Courses

777 members asked questions and received personalized solutions in the past 7 days.

Join the community of 500,000 technology professionals and ask your questions.

Join & Ask a Question