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.

==> (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) '250-8BITMIME\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.


Anonymous 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:

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


from the server it's authenticataing fine.

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