Mail relaying problem, cannout mail from outside network using outlook
 

Not sure which thread to put this in so I thought I would start here

OpenSUSE 10 Mail problem

I have OpenSuse running Sendmail and Cyrus and all works well but when I go to an external computer (Outside of my network) and try to connect Outlook to is I have the following issue:

I can read and receive all mail normally but when I try to send a message Outlook asks me to "Enter Network Password", this I do but is simply does not accept it. The mail log has the following message

Mar 30 15:59:52 hatchnet sendmail[9877]: n2U4xq98009877: 162.133-26-211.corp.syd.iprimus.net.au [211.26.133.162] did not issue MAIL/EXPN/VRFY/ETRN during connection to MTA


I can use Horde and Squirrel for send and receive without problems

I have the Checkbox "My outgoing server (SMPT) requires authentication" checked in the Outgoing server tab of more settings in the Outlook email account setup and I have tries "Use the same settings as my outgoing server" and "log on using" with my valid credentials.

Any ideas any, Ive been googling and mucking about with this for days now..

Oh, heres the sendmail.mc

divert(-1)
include(`/usr/share/sendmail/m4/cf.m4')
divert(0)
VERSIONID(`Sendmail Config for hatchnet 2008-05-03')
OSTYPE(`linux')
DOMAIN(`generic')
define(`ALIAS_FILE', `/etc/aliases')

LOCAL_NET_CONFIG
R$* < @ $* .$m. > $* $#esmtp $@ $2.$m $: $1 < @ $2.$m. > $3
define(`confMILTER_LOG_LEVEL',`1')
RELAY_DOMAIN_FILE(`/etc/mail/relay-domains')
FEATURE(`use_cw_file')
FEATURE(`relay_entire_domain')
FEATURE(masquerade_envelope)
FEATURE(local_procmail)
define(`confAUTH_OPTIONS', `A')
TRUST_AUTH_MECH(`EXTERNAL DIGEST-MD5 CRAM-MD5 LOGIN PLAIN')dnl
define(`confAUTH_MECHANISMS', `EXTERNAL GSSAPI DIGEST-MD5 CRAM-MD5 LOGIN PLAIN')dnl
define(`confLOCAL_MAILER', `cyrusv2')
MAILER(smtp)
MAILER(procmail)
MAILER(local)
MAILER(`cyrusv2')

How are you connecting to your server from the outside world?

Do you have a TLD that is routed to your server?

Does your ISP give you a static IP or dynamic?

Are you going through a router at the server location? Is it port forwarded for SMTP?

If you are using a dynamic IP address from your ISP, does your router assign a static IP address to your server?

I had the same issues using ubuntu 8.10+postfix+courier and after I set all the routing up properly it didn't give me any more problems.

Is there some reason that you can't just use your isp smtp?

I am trying to connect to my server using Outlook from a remote workstation

I run my own mail and web server with a static ip and want to relay mail for some colleagues as a favour as I am running mail for them already using squirrel (they want to use outlook, hence the problem)

Telnetting to port SMTP port 25 gives the following

telnet 60.229.255.190 25
Trying 60.229.255.190...
Connected to CPE-60-229-255-190.static.nsw.bigpond.net.au (60.229.255.190).
Escape character is '^]'.
220 hatchnet.hatchnet.com.au ESMTP Sendmail 8.14.1/8.14.1; Tue, 31 Mar 2009 10:20:31 +1100

Which kind of looks normal to me

telnetting to 143 gives

telnet 60.229.255.190 143
Trying 60.229.255.190...
Connected to CPE-60-229-255-190.static.nsw.bigpond.net.au (60.229.255.190).
Escape character is '^]'.
* OK [CAPABILITY IMAP4 IMAP4rev1 LITERAL+ ID AUTH=DIGEST-MD5 SASL-IR] hatchnet Cyrus IMAP4 v2.3.8 server ready

Also okay i guess

I don't know if its required anymore as I don't use sendmail much but I think you need to have to put the domains of the hosts that you want to be able to relay in your server in /etc/relay/mail-domains

Okay then, clearly it is a relaying problem because if i set

FEATURE(promiscuous_relay)

It works, clearly I can't have that in my config though. The user who is sending mail externally is not in my domain and I don't want to let his entire domain use me as a relay so I want him to authenticate his connection but when I do that, sendmail doesn't like it and gives the message already shown.