Cannot send mail from email clients (Resolved)

[zmediaguru]

There must be something really simple I'm missing here... I've been reading through threads and trying various things all evening.

Whenever I try to send messages from an email client (Thunderbird, Apple Mail, etc) with smtp authentication setup in the client, I am prompted over and over for my password, and cannot send messages through Scalix.

Here is what I have in my smtpd.cfg file:

SMTPFILTER=TRUE

RELAY accept 127.0.0.1
RELAY accept .sureclient.net
AUTH_SUCCESS accept ALL
DEBUG_LOG=TRUE
RELAY Log_Reject ALL

RECIPIENT Log_Reject *@*@*
RECIPIENT Log_Reject *%*
RECIPIENT Log_Reject *!*
RECIPIENT Log_Reject *#*@*

[SUBMIT]
#LISTEN=localhost:587
# Reject all anonymous connections
ANONYMOUS Log_Reject ALL

Here's the output of omstat -a:

PC Monitor Started NON-STOP 0
Directory Relay Server Started 23:32:48
Notification Server Started 23:32:48 0
Shared memory daemon Started NON-STOP
Notification Monitor Started NON-STOP
Session Monitor Started NON-STOP
Indexer Started NON-STOP
Stats Daemon Started NON-STOP
Container Access Monitor Started NON-STOP
Item Structure Server Stopped
Database Monitor Started 23:32:48
Licence Monitor Daemon Started NON-STOP
LDAP Daemon Started 23:32:48
Queue Manager Started NON-STOP
Item Delete Daemon Started NON-STOP
IMAP Server Daemon Started 23:32:48
SMTP Relay Started 23:32:48
Mime Browser Controller Started 23:32:48
Event Server Started 23:32:48

When I telnet to port 25 from an external machine, I get the following greeting, which looks correct to me:

Connected to scalix.domain.tld.
Escape character is '^]'.
220 scalix.domain.tld ESMTP Scalix SMTP Relay 11.3.0.11339; Thu, 24 Jan 2008 23:57:50 -0600 (CST)

I'm not seeing any successful authentications in smtpd-SMTP.log.

What is preventing the email clients from authenticating? and what do I need to change to be able to send messages from the email clients?

[zmediaguru]

To add to the notes above, my local ISP blocks port 25, so I have Stunnel configured as follows:

[ssmtp]
accept = 465
connect = 25

My email client applications are also configured to use SSL on port 465

Note: To clarify about port 25, was able to test the port 25 connection above from command line on another server, I am not able to test an actual email client from that machine.

[zmediaguru]

Here is the reply my email client is getting when I try to send via SSL port 465 with SMTP Authentication:

[*] Connection established to xxx.xxx.xxx.xxx
>> 0089 220 scalix.domain.tld ESMTP Sendmail 8.13.8/8.13.8; Fri, 25 Jan 2008 12:33:47 -0600
<< 0022 EHLO [192.168.1.200]
>> 0088 250-scalix.domain.tld Hello localhost.localdomain [127.0.0.1], pleased to meet you
>> 0025 250-ENHANCEDSTATUSCODES
>> 0016 250-PIPELINING
>> 0014 250-8BITMIME
>> 0010 250-SIZE
>> 0009 250-DSN
>> 0010 250-ETRN
>> 0030 250-AUTH DIGEST-MD5 CRAM-MD5
>> 0015 250-DELIVERBY
>> 0010 250 HELP
<< 0015 AUTH CRAM-MD5
>> 0066 334 PDIzNzE3NDUwODcuMTAxMDM3NjJAc2NhbGl4LnN1cmVjbGllbnQubmV0Pg==
<< 0074 dGltQHVtYXNzb2NpYXRlcy5jb20gNTkxNWU2NTNkY2IyNGY1MjU2NDBkYzU2OTdiM2IwYjc=
>> 0033 535 5.7.0 authentication failed

It will, however now open relay without SMTP Authentication on port 465, which is NOT a good thing.

[zmediaguru]

Okay, we're looking better... we were able to test SMTP relay from an email client through port 25, and it all looks good.

This means that we're now down to the known issue with Stunnel routing to Sendmail vs. SMTP Relay on local port 25. I'm currently trying suggestions found elsewhere on this forum, if anyone has any suggestions, I'm all ears.

[zmediaguru]

For anyone watching me talk to myself, I finally got everything working how I want it to after lots of trial and error.

Here's the 'recipe' of what I did, in case it's helpful to anyone else:

1) Enable Submission in /var/opt/scalix/xx/s/sys/smtpd.cfg:
- Uncommented SUBMIT=ON
- Used default port 587 for Submission

This tells Scalix SMTP Relay to listen for relays on port 587. This is helpful for users (like me) using ISPs that block port 25. It will only accept authenticated connections, so will NOT create an open relay on this port.

2) Restart SMTP Relay:

#omoff smtpd
#omon smtpd

3) Point Stunnel to connect to 587 for ssmtp:

[ssmtp]
accept = 465
connect = 587

This tells Stunnel to accept SSL connections on port 465 and connect them to port 587. See above, as Submission will ONLY accept authenticated users, it does not create an open relay on this port, either.

4) Restart Stunnel

That's really all there is to it. Verify that SMTP relay is running by checking

omstat -a