SASL Authentication For Mail Server (Sendmail/Postfix)

Mar 18, 2007

I recently moved to virtual dedicated hosting for my website, mainly because I wanted a better mail server to work with to manage a mailing list.

I have a few PHP software scripts for different things: managing affiliates and email marketing.

I want to send mail using both of those via SMTP on my new server. They both have a place to type in the host and username/password.

The problem I am noticing is SASL Authentication. They attempt to connect to the host without any trouble. However, the affiliate software fails SASL Authentication every time I try to send an email or test the email system.

Email marketing software connects when I manually send a campaign. However, users are supposed to immediately receive a confirmation mail upon opting in. In this case, it shows up as an attempt in the mail log, but it fails SASL Authentication. I don't know if it's a problem with the software or not, since it attempts to connect but fails, yet connects successfully in other cases.

My question is this: Is there another way around this? I've contacted my host to double check on the appropriate username/password to pass authentication. I will also be contacting the software developers after I receive an answer.

But if nothing comes of it, is there any way around it? Is there a place where I can have it automatically authenticate if the email is coming from a certain user, or if the attempt is being made from the same server (everything sits on the same server, I use localhost in the software to connect to the mail server). Since I am the only person who has access to the server and uses it, it seems safe to automatically authenticate if the request is being asked by the server itself...

I'm just looking for other alternatives if the software does indeed have a problem and I cannot figure it out.

Keep in mind I am very new to all this server and root access. Just a few days ago I was on a shared hosting plan, so I didn't have any access to anything. With that in mind, I know very little about mail servers, although I've been learning more over the past few days. I only stumbled upon the mail logs on my server recently by browsing files in the control panel (I'm not familiar with SSH, although I do have access to it)

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Jan 24, 2013

I have a new Plesk 11.0.9. #34 server with Centos 6.3 64bit.

I made a few changes in order to be PCI Compliant.

I created a domain and try to send email with no luck.

----------Maillog------------
Jan 24 16:01:28 server7 pop3d-ssl: Connection, ip=[::ffff:X.X.X.X]
Jan 24 16:01:34 server7 pop3d-ssl: IMAP connect from @ [::ffff:X.X.X.X]ERR: LOGIN FAILED, ip=[::ffff:X.X.X.X]
Jan 24 16:01:34 server7 pop3d-ssl: Unexpected SSL connection shutdown.
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[Code] ....

As you can see from the logs, the pop/imap connection is successful. I login to webmail with the username/password successfully. I can't send from Outlook/thunderbird etc.

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Code:
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At the last Plesk upgrade, my Request Tracker installation can no longer use sendmail to send email directly from the server.

The errors I am getting are:
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There my configuration files.

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queue_directory = /var/spool/postfix
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daemon_directory = /usr/libexec/postfix

[Code].....

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Since then, all mails sent using the sendmail binary (notifications, mail forwards...) are being rejected with a wrong HELO hostname: localhost.

It seems that sendmail is using locahost as a HELO tag which is not accepted. Here is the following error:

Code:

Jun 23 14:23:20 ns395167 plesk sendmail[29817]: handlers_stderr: SKIP
Jun 23 14:23:20 ns395167 plesk sendmail[29817]: SKIP during call 'check-quota' handler
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[Code] .....

Here is my postconf -n content:

Code:

alias_database = hash:/etc/aliases
alias_maps = hash:/etc/aliases, hash:/var/spool/postfix/plesk/aliases
command_directory = /usr/sbin
config_directory = /etc/postfix
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[code] .....

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Code:
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ns395167.ip-176-31-117.eu
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A better title might be "hotmail or yahoo won't accept the emails from sendmail."

I have sendmail version: 8.13.4

I have the only modification I can remember doing is:
MASQUERADE_AS(`ipalaces.org')dnl

I can send emails perfectly to gmail accounts. Here is a sucessfull output of an email send to gmail:

Quote:

Delivered-To: paroxsitic@gmail.com
Received: by 10.114.113.11 with SMTP id l11cs366927wac;
Thu, 29 Mar 2007 10:05:09 -0700 (PDT)
Received: by 10.70.80.14 with SMTP id d14mr1879830wxb.1175187909424;
Thu, 29 Mar 2007 10:05:09 -0700 (PDT)
Return-Path: <root@ipalaces.org>
Received: from ipalaces.org (ipalaces.org [64.74.153.24])
by mx.google.com with ESMTP id h40si1247663wxd.2007.03.29.10.05.09;
Thu, 29 Mar 2007 10:05:09 -0700 (PDT)
Received-SPF: pass (google.com: best guess record for domain of root@ipalaces.org designates 64.74.153.24 as permitted sender)
Received: from ipalaces.org (ipalaces.org [127.0.0.1])
by ipalaces.org (8.13.4/8.13.4/Debian-3sarge3) with ESMTP id l2TH58SJ005383
for <paroxsitic@gmail.com>; Thu, 29 Mar 2007 13:05:08 -0400
Received: (from root@localhost)
by ipalaces.org (8.13.4/8.13.4/Submit) id l2TH51kd005299
for paroxsitic@gmail.com; Thu, 29 Mar 2007 13:05:01 -0400
Date: Thu, 29 Mar 2007 13:05:01 -0400
From: root <root@ipalaces.org>
Message-Id: <200703291705.l2TH51kd005299@ipalaces.org>
To: undisclosed-recipients:;

This is a test of the body.

I originally thought the reason hotmail or yahoo didn't receive my emails was because I had no reverse DNS for the IP I was sending the emails out with. Therefore I had my VPS provider create one for my IP. It now reflects ipalaces.org with the IP I use to send out emails (64.74.153.24)

Even after the reverse DNS in place, hotmail nor yahoo could recieve my emails. I am now pretty much stump as to why. I have googled and scanned various other solutions and I havent found anything.

Here is a verbose output of using sendmail to an hotmail address of mine:

Quote:

ek_opteron@hotmail.com... Connecting to [127.0.0.1] port 587 via relay...
220 ipalaces.org ESMTP Sendmail 8.13.4/8.13.4/Debian-3sarge3; Thu, 29 Mar 2007 1 3:07:17 -0400; (No UCE/UBE) logging access from: ipalaces.org(OK)-ipalaces.org [ 127.0.0.1]
>>> EHLO ipalaces.org
250-ipalaces.org Hello ipalaces.org [127.0.0.1], pleased to meet you
250-ENHANCEDSTATUSCODES
250-PIPELINING
250-EXPN
250-VERB
250-8BITMIME
250-SIZE
250-DSN
250-ETRN
250-AUTH DIGEST-MD5 CRAM-MD5
250-DELIVERBY
250 HELP
>>> VERB
250 2.0.0 Verbose mode
>>> MAIL From:<root@ipalaces.org> SIZE=15 AUTH=root@ipalaces.org
250 2.1.0 <root@ipalaces.org>... Sender ok
>>> RCPT To:<ek_opteron@hotmail.com>
>>> DATA
250 2.1.5 <ek_opteron@hotmail.com>... Recipient ok
354 Enter mail, end with "." on a line by itself
>>> .
050 <ek_opteron@hotmail.com>... Connecting to mx3.hotmail.com. via esmtp...
050 220 bay0-mc8-f1.bay0.hotmail.com Sending unsolicited commercial or bulk e-ma il to Microsoft's computer network is prohibited. Other restrictions are found a t http://privacy.msn.com/Anti-spam/. Violations will result in use of equipment located in California and other states. Thu, 29 Mar 2007 10:07:17 -0700
050 >>> EHLO ipalaces.org
050 250-bay0-mc8-f1.bay0.hotmail.com (3.3.2.16) Hello [64.74.153.24]
050 250-SIZE 29696000
050 250-PIPELINING
050 250-8bitmime
050 250-BINARYMIME
050 250-CHUNKING
050 250-AUTH LOGIN
050 250-AUTH=LOGIN
050 250 OK
050 >>> MAIL From:<root@ipalaces.org> SIZE=320 AUTH=<>
050 250 root@ipalaces.org....Sender OK
050 >>> RCPT To:<ek_opteron@hotmail.com>
050 >>> DATA
050 250 ek_opteron@hotmail.com
050 354 Start mail input; end with <CRLF>.<CRLF>
050 >>> .
050 250 <200703291707.l2TH7DSt007328@ipalaces.org> Queued mail for delivery
050 <ek_opteron@hotmail.com>... Sent ( <200703291707.l2TH7DSt007328@ipalaces.org > Queued mail for delivery)
250 2.0.0 l2TH7HeD007332 Message accepted for delivery
ek_opteron@hotmail.com... Sent (l2TH7HeD007332 Message accepted for delivery)
Closing connection to [127.0.0.1]
>>> QUIT
221 2.0.0 ipalaces.org closing connection

The main thing that strikes out to me is that hotmail says "Queued mail for delivery" whereas Gmail normally says "OKAY". It seems as hotmail gets the email, and then decides it's no good. I don't know if my IP is blacklisted or I have to change something in my configuration from 127.0.0.1 to my IP, or what I have to do.

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