Comments on: Outlook 2007 MD5 SMTP auth broken

By: john

john — Thu, 18 Aug 2011 05:09:12 +0000

I had the same problem and i found this website called http://www.outlooksetting.com , they had a whole range of troubleshooting articles. Really helpful stuff. Check it out!

By: Outlook & IMAP: define “better” |

Outlook & IMAP: define “better” | — Sun, 20 Feb 2011 07:34:17 +0000

[...] to set up an email account with MD5 authentication, fetching mail off a Mac server. Apparently, no recent version of Outlook knows how to do this. This is still SMTP, but its with MD5 challenge. No can do, says my Outlook client. And I guess [...]

By: Jeroen

Jeroen — Thu, 15 Jul 2010 20:48:09 +0000

Hi,

Outlook 2010 still seems to have problems with DIGEST-MD5 as Steve pointed out in 2007 for OL2007.

With my IMAP connection I can not get the outlook 2010 to work (MD5 digest authentication fails – and I can asure you that password is 100% correct).

Does anybody know how to avoid that MD5 is being used in OL2010 (I can not control mailserver). OL2003 uses plain for AUTH.

Cheers
Jeroen

By: Steven Haigh

Steven Haigh — Thu, 07 Jan 2010 08:34:49 +0000

Hi Charles,

Silly question, but after editing sendmail.mc, you ran make sendmail.cf, then restarted sendmail?

From the sounds of things, something was missed while editing sendmail.mc…

By: Charles Otine

Charles Otine — Thu, 07 Jan 2010 06:36:20 +0000

I am having a problem where Thunderbird users are able to send mail using our Sendmail SMTP server after authentication but Outlook 2007 users keep receiving a prompt to enter the password again and again and then fail to send the mail. I have examined the mail logs and it indicates the error “[IP Address] did not issue MAIL/EXPN/VRFY/ETRN during connection to MTA” I google this error and there were many opinions but one indicated that this shows that outlook was connecting to the MTA but afterward would not give the MTA any further recognizable commands.

Steve, I am using sendmail 8.14.3 and when i perform the EHLO command the 250-AUTH.. does not show PLAIN LOGIN, it only shows DIGEST-MD5 CRAM-MD5.Attempts to edit the sendmail.mc as indicated in your tutorial have not made a change. Is there any further work around on this issue?

By: Don Resnick

Don Resnick — Tue, 04 Aug 2009 19:29:08 +0000

In my case, it is RECEIVING mail that is having this problem — and only with IMAP accounts. Outlook 2007 is trying to use DIGEST-MD5 and failing. Outlook 2003 does not have this problem.

I have the same question as Sergey: Is there a way to get Outlook 2007 to stop using DIGEST-MD5?

Note that this thread is one year old; Outlook is in Service Pack 2; and this STILL hasn’t been addressed!

By: Sergey

Sergey — Sat, 23 Aug 2008 21:30:52 +0000

How is it possible to configure ms outlook 2007 to use only login or plain auth without md5. Anybody knows?

By: Rick Romero

Rick Romero — Thu, 21 Aug 2008 14:40:27 +0000

PLAIN and LOGIN are quite popular, and easy to implement. If security is an issue, running over SSL is always an option.

By: Larry

Larry — Tue, 15 Jul 2008 15:07:49 +0000

Can you disable MD5 AUTH in Outlook?
I think after a recent security update, it looks like my Outlook 2007 client is now ALWAYS trying AUTH DIGEST-MD5 and failing and then trying AUTH LOGIN. I don’t think I changed any Outlook setting to cause this. What happened?

By: Mario Ruprecht

Mario Ruprecht — Tue, 15 Jan 2008 17:59:20 +0000

Hi Steve,

thanks for pointing this out. I’m experionecing exactly the same issue after I upgraded to Outlook 2007.

Did you find in the meantime something which can be done on the client side to avoid this problem?

Thanks, Mario