April 10, 2008

Outlook is Driving Me Nuts!

[UPDATE: two changes were required. First I had to set broken_sasl_auth_clients = yes in my postfix main.cf, then I had to add login as an available authentication mechanism in dovecot, which postfix uses as an authentication server. Thanks for all pointers and suggestions, some of which came by e-mail. Not quite as stupid and fundamental as I feared. Steve].

OK, I am in serious need of assistance here. I suspect that there must be something really stupid and fundamental that I am overlooking. The problem is that I cannot get Outlook 2003 to authenticate to its SMTP server.

I have tried deleting the account and recreating it (shutting Outlook down in between). I have verified that the same settings in a Thunderbird client allow me to send mail without difficulty. I have even installed Outlook on an entirely separate computer and got the same dismal results.

Why Outlook? Well, although I am a Thunderbird user myself my wife uses Outlook. So my most important support client has a problem -- only with sending mail, though, receiving works fine.

Just so you can visually verify that I haven't done anything stupid, here are screen shots of the relevant dialogs. I have even set up a local printing SMTP proxy to verify what's happening! With Thunderbird it clearly shows an AUTH command being send to the server, but with good 'ole Outlook I get what you see below (slightly redacted): straight from EHLO to MAIL with no AUTH at all.

Connected
==> (0) '220 holdenwe.user.openhosting.com ESMTP Postfix\r'
<== (0) 'EHLO DoroPC\r' ==> (0) '250-holdenwe.user.openhosting.com\r'
==> (0) '250-PIPELINING\r'
==> (0) '250-SIZE 10240000\r'
==> (0) '250-VRFY\r'
==> (0) '250-ETRN\r'
==> (0) '250-AUTH PLAIN\r'
==> (0) '250-ENHANCEDSTATUSCODES\r'
==> (0) '250-8BITMIME\r'
==> (0) '250 DSN\r'
<== (0) 'MAIL FROM: <xxxx@holdenweb.com>\r'
==> (0) '250 2.1.0 Ok\r'
<== (0) 'RCPT TO: <xxxx@gmail.com>\r'
==> (0) '554 5.7.1 <xxxx@gmail.com>: Relay access denied\r'
<== (0) 'QUIT\r'

So, if you can tell me what's wrong you may rescue my sanity! Help me, please, this is driving me nuts.


7 comments:

Jerry said...

Looks right to me. Have you tried turning on logging in Outlook? Both Outlook and Outlook Express have a logging facility. It's been so long since I've used Outlook for anything but at work, that I don't remember where it is. Try searching the help file for it.

Marius Gedminas said...

I usually avoid Microsoft products like the plague, so what I'm going to say comes not from first-hand experience, but from reading documentation. Postfix has a special option that enables compatibility with broken e-mail clients such as Outlook Express version 4. That option makes the SMTP server advertise SMTP AUTH support in a non-standard way that Outlook Express expects.

Here's the documentation I mentioned.

Perhaps Outlook 2003 also needs something like that?

Anonymous said...

I dont see anywhere in the trace you provided that outlook sent an AUTH command. the 250 msgs are just what the server supports.
it should look soething like this:

C : AUTH PLAIN
S : 334 Username:
C : myname
S : 334 Password:
C : mypass
S : 235 Go Ahead

Steve said...

Well the fact that Outlook wasn't sending an AUTH was kind of the point of the whole post. But the REASON it wasn't sending it (despite having been set to) was because Outlook requires a non-standard AUTH message (it has to have an equals sign in it). I also had to adjust it to offer the LOGIN authentication method, since Outlook doesn't do PLAIN. Now Outlook sees

250-AUTH=PLAIN LOGIN

from the server it's authenticataing fine.

Alex said...

I know a lot of tool in sphere mails,but almost all of it aren't good,because they has many minuses,besides that there is one tool-outlook express recover deleted messages,which marks of them,it is free as is known and has many good admissibilities,on example it can process dbx files regardless of the cause of their damage,supports even batch mode recovering,compatible with Windows NT 4.0, Windows Me, Windows 98, Windows 2000, Windows 2003, Windows XP, Windows Vista and all versions of Outlook Express, currently supported by Microsoft Corporation,recover deleted Outlook Express email, because it is very important to start working with this program and recover deleted messages Outlook Express to prevent further corruption of dbx files,program can restore the data, that was destroyed by viruses, hardware errors and other faults.

Alexis said...

At convert or similar actions I try to use-convert pst files.Because this tool can both recover all data too and it is free as far as I know.Moreover application compatible with Windows 98, Windows Me, Windows NT 4.0, Windows 2000, Windows XP, Windows 2003 and Windows Vista.

Alex said...

I often solve problems with help one nice tool.But last time program couldn't help me.And I entered in network and saw there-convert .ost file to .pst file.Application helped me very quickly and for free.Moreover soft demonstrated how it works with ost files in Outlook and belongs to ost to pst conversion software and can repair files with *.ost extension.