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.

Cygwin ssh-agent Control

[Edited: 10/6/08 Remove temporary files before starting a new agent]

Another little annoyance gone: all Cygwin processes now share a single ssh-agent instance, which is started up automatically as required. I picked this tip up from a now-forgotten blog. the only change required to that recipe being to re-order the redirections for the ssh-agent command. Since it took me a while to find (low Google-fu today?) I take the liberty of repeating it here so I don't forget it.

In your ~/.bashrc file add the following:

export SSH_AUTH_SOCK=/tmp/.ssh-socket

ssh-add -l >/dev/null 2>&1
if [ $? = 2 ]; then
# Exit status 2 means couldn't connect to ssh-agent; start one now
rm -rf /tmp/.ssh-*
ssh-agent -a $SSH_AUTH_SOCK >/tmp/.ssh-script
. /tmp/.ssh-script
echo $SSH_AGENT_PID >/tmp/.ssh-agent-pid
fi


function kill-agent {
pid=`cat /tmp/.ssh-agent-pid`
kill $pid
}


You can use Start | My Computer | Properties | Advanced | Environment Variables to add an environment variable called SSH_AUTH_SOCK whose value is /tmp/.ssh-socket to make the agent available to other Cygwin-aware processes you run under Windows.

That's better!

For some reason a number of posts were stuck in the blog as drafts. This one is from October last year.