Article ID: 114739, created on Sep 10, 2012, last review on May 11, 2014

  • Applies to:
  • Plesk 11.x for Linux
  • Plesk 10.4 for Linux/Unix

Symptoms

The mail server installed with the PP distribution rejects messages from bigfish.com with the following message:

An error occurred while trying to deliver this message to the recipient's e-mail address. Microsoft Exchange will not try to redeliver this message for you. Please try resending this message, or provide the following diagnostic text to your system administrator.


The diagnostic text in this case will have the following data recorded:

The following organization rejected your message: mail.ourmailserver.net.

Generating server: bigfish.com

user@domain.tld<mailto:user@domain.tld>
mail.ourmailserver.net #<mail.ourmailserver.net #5.0.0 smtp;554 mail server permanently rejected message> #SMTP#

uesr2@domain.tld<mailto:user2@domain.tld>
mail.mailserver.net #<mail.ourmailserver.net #5.0.0 smtp;(10.9.99.132) with Microsoft SMTP Server (TLS) id 14.1.225.23; Wed, 21 Mar
2012 08:30:05 +0000
Received: from NASLSWAMG040.na.domainx.com ([10.21.35.46]) by
NASLSWAMS052.na.domainx.com ([10.21.29.11]) with mapi; Wed, 21 Mar 2012
04:30:07 -0400
F
Date: Wed, 21 Mar 2012 04:30:06 -0400
Subject: WG: {Disarmed} PRE ALERT: Decotrade AG ex userdomain - Approval of
sample o.ref. 59-23365 / 395-11633 - Booking Ref - 863644237
Thread-Topic: {Disarmed} PRE ALERT: Decotrade AG ex userdomain - Approval of
sample o.ref. 59-23365 / 395-11633 - Booking Ref - 863644237
Thread-Index: Ac0GqGaBuLuN5EZnTjWP6WCs/DQIEAAk5magAAAxTzA=
Message-ID: <E092440E9321E744A62E4279E8E957F20194E5982(10.9.99 .132) with Microsoft SMTP Server (TLS) id 14.1.225.23; Wed, 21 Mar
2012 08:30:05 +0000
Received: from NASLSWAMG040.na.domainx.com ([10.21.35.46]) by
NASLSWAMS052.na.domainx.com ([10.21.29.11]) with mapi; Wed, 21 Mar 2012
04:30:07 -0400

Date: Wed, 21 Mar 2012 04:30:06 -0400
Subject: WG: {Disarmed} PRE ALERT: Decotrade AG ex userdomain - Approval of
sample o.ref. 59-23365 / 395-11633 - Booking Ref - 863644237
Thread-Topic: {Disarmed} PRE ALERT: Decotrade AG ex userdomain - Approval of
sample o.ref. 59-23365 / 395-11633 - Booking Ref - 863644237
Thread-Index: Ac0GqGaBuLuN5EZnTjWP6WCs/DQIEAAk5magAAAxTzA=
Message-ID: <E092440E9321E744A62E4279E8E957F20194E5982C16@NASL SWAMG040.na.domainx.com<mailto:E092440E9321E744A62 E4279E8E957F20194E5982C16@NASLSWAMG040.na.domainx. com>>

Return-Path: 
X-OriginatorOrg: domainx.com
C16@NASLSWAMG040.na.domainx.com<mail.... domainx.com>>

Return-Path: user@domainx.com<mailto:user@domainx.com>
X-OriginatorOrg: domainx.com
554 mail server permanently rejected message> #SMTP#

admin@domain.tld<mailto:admin@domain.tld>
mail.ourmailserver.net #<mail.ourmailserver.net #5.0.0 smtp;554 mail server permanently rejected message> #SMTP#

Original message headers:

Received: from mail83-tx2-R.bigfish.com (10.9.14.238) by
TX2EHSOBE007.bigfish.com (10.9.40.27) with Microsoft SMTP Server id
14.1.225.23; Wed, 21 Mar 2012 08:30:08 +0000(10.9.99.132) with Microsoft SMTP Server (TLS) id 14.1.225.23; Wed, 21 Mar
2012 08:30:05 +0000
Received: from NASLSWAMG040.na.domainx.com ([10.21.35.46]) by
NASLSWAMS052.na.domainx.com ([10.21.29.11]) with mapi; Wed, 21 Mar 2012

Date: Wed, 21 Mar 2012 04:30:06 -0400
Subject: WG: {Disarmed} PRE ALERT: Decotrade AG ex userdomain - Approval of
sample o.ref. 59-23365 / 395-11633 - Booking Ref - 863644237
Thread-Topic: {Disarmed} PRE ALERT: Decotrade AG ex userdomain - Approval of
sample o.ref. 59-23365 / 395-11633 - Booking Ref - 863644237
Thread-Index: Ac0GqGaBuLuN5EZnTjWP6WCs/DQIEAAk5magAAAxTzA=
Message-ID: <E092440E9321E744A62E4279E8E957F20194E5982C16@NASL SWAMG040.na.domainx.com<mailto:E092440E9321E744A62 E4279E8E957F20194E5982C16@NASLSWAMG040.na.domainx. com>>
S
x-exclaimer-md-config: c5a3f742-9dc9-4dd9-9539-5e407d231d79
Content-Type: multipart/alternative;
boundary="_000_E092440E9321E744A62E4279E8E957F2019 4E5982C16NASLSWAMG04_"
MIME-Version: 1.0
Return-Path: user@domainx.com
X-OriginatorOrg: domainx.com

Cause

The root cause of the issue is that Microsoft has included the word pool in their exchange relay. If you watch your mail queue in real time, you will see something like "db3outboundpool.messaging.microsoft.com" whenever there are inbound exchange messages.

Whenever PP is greylisting, the service has an overriding blacklist of the following:
 
*[0-9][0-9]-[0-9][0-9]-[0-9][0-9]*
*[0-9][0-9].[0-9][0-9].[0-9][0-9]*
*[0-9][0-9][0-9]-[0-9][0-9][0-9]-[0-9][0-9][0-9]*
*[0-9][0-9][0-9].[0-9][0-9][0-9].[0-9[0-9]][0-9]*
dsl|pool|broadband|hsd
dynamic|static|ppp|dyn-ip|dial-up

Therefore, with the greylisting feature enabled, MTA will reject any inbound exchange messages from hosts that contain the word pool.

Resolution

In order to resolve the issue, you should explicitly whitelist the Microsoft exchange relay by running the following command:

# /usr/local/psa/bin/grey_listing --update-server -domains-whitelist "add:*messaging.microsoft.com"

e8756e9388aeca36710ac39e739b2b37 56797cefb1efc9130f7c48a7d1db0f0c a914db3fdc7a53ddcfd1b2db8f5a1b9c 29d1e90fd304f01e6420fbe60f66f838 dd0611b6086474193d9bf78e2b293040 0a53c5a9ca65a74d37ef5c5eaeb55d7f

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