On Fri, 11 Apr 2008, Tim Mancour wrote:
> Rather a mystery - have you try the submission port (587)? I would attempt
> to watch the SMTP conversation between these clients and your toaster using
> Ethereal or similar application. I've found the following useful for
> debugging SMTP_AUTH issues http://qmail.jms1.net/test-auth.shtml, although
> it seems like something (perhaps a firewall?) is obstructing the AUTH
> command.
OK, I've managed to do several tests, and set up wireshark to watch the
SMTP converstation between our client's outlook/thunderbird and my toaster
What baffles me here is that while both outlook (fully patched, all
service packs), and thunderbird are set up to use SMTP-AUTH, neither ever
seem to make the attempt.
For example, here's a transcript of when thunderbird tries to send a
test email (courtesy of wireshark):
-----------------------------------
220 *************************************************************************
EHLO [127.0.0.1]
502 unimplemented (#5.5.1)
HELO [127.0.0.1]
250 my.toaster.com - Welcome to Qmail Toaster Ver. 1.3 SMTP Server
MAIL FROM:<[EMAIL PROTECTED]>
250 ok
RCPT TO:<[EMAIL PROTECTED]>
553 sorry, that domain isn't in my list of allowed rcpthosts (#5.5.3 - chkuser)
QUIT
221 my.toaster.com - Welcome to Qmail Toaster Ver. 1.3 SMTP Server
-------------------------
And here's outlook's transcript (also courtesy of wireshark):
------------------------
220 *************************************************************************
EHLO MYWINDOWSHOSTNAME
502 unimplemented (#5.5.1)
HELO MYWINDOWSHOSTNAME
250 my.toaster.com - Welcome to Qmail Toaster Ver. 1.3 SMTP Server
MAIL FROM: <[EMAIL PROTECTED]>
250 ok
RCPT TO: <[EMAIL PROTECTED]>
553 sorry, that domain isn't in my list of allowed rcpthosts (#5.5.3 - chkuser)
QUIT
221 my.toaster.com - Welcome to Qmail Toaster Ver. 1.3 SMTP Server
--------------------------
Again, if I connect from outside the client's LAN with either Tbird or
Outlook, all is well and I can relay mail.
If I telnet to my toaster from the client's LAN and do a manual SMPT-AUTH
test, I can relay, no problem.
If I look at the client's LAN's outward facing router, I see:
--------------------------
PORT STATE SERVICE
21/tcp filtered ftp
22/tcp open ssh
25/tcp filtered smtp
53/tcp filtered domain
80/tcp filtered http
110/tcp filtered pop3
123/tcp filtered ntp
143/tcp filtered imap
220/tcp filtered imap3
443/tcp filtered https
993/tcp filtered imaps
1984/tcp filtered bigbrother
3306/tcp filtered mysql
----------------------
Is there something here that should be open that isn't?
And why in heck are both outlook and tbird seemingly skipping the AUTH
step in the SMTP conversation?
Any suggestions/theories, etc., would be greatly appreciated...
--Duncan
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