Want to highlight a helpful answer? Upvote!

Did someone help you, or did an answer or User Tip resolve your issue? Upvote by selecting the upvote arrow. Your feedback helps others! Learn more about when to upvote >

Looks like no one’s replied in a while. To start the conversation again, simply ask a new question.

e-mail bouncing PERM_FAILURE message content rejected for policy reasons

I get the foll. error when sending e-mail from Apple Email (IMAP configuration).
But the e-mail sent from a web front-end to Google is successfully delivered.
Can somebody help me out? I have the same problem with two other e-mail accounts sent to the same addressee. I am able to communicate using Apple Mail with other correspondents.

Thanks
MN

PS
e-mail addresses and IP numbers have been modified for security reasons.

This is an automatically generated Delivery Status Notification

Delivery to the following recipient failed permanently:

xyz@abc.ch

Technical details of permanent failure:
PERM_FAILURE: Gmail tried to deliver your message, but it was rejected by the recipient domain. We recommend contacting the other email provider for further information about the cause of this error. The error that the other server returned was: 552 552 5.2.0 Message content rejected for policy reasons (state 17).

----- Original message -----

Received: by z0.1x3.45.y1 with SMTP id x21mr3364997wfj.221.1212382619597;
Sun, 01 Jun 2008 21:56:59 -0700 (PDT)
Return-Path: <abc@gmail.com>
Received: from ?192.168.1.61? ( [1x2.1y4.z6.238])
by mx.google.com with ESMTPS id 28sm6247477wfd.4.2008.06.01.21.56.48
(version=TLSv1/SSLv3 cipher=RC4-MD5);
Sun, 01 Jun 2008 21:56:58 -0700 (PDT)
Message-Id: <54519E9A-5275-4081-BB75-CF9AA6C48530@gmail.com>
From: Name1 <abc@gmail.com>
To: Name2 <xyz@abc.ch>
Content-Type: multipart/alternative; boundary=Apple-Mail-3--313351
Mime-Version: 1.0 (Apple Message framework v919.2)
Subject: =?ISO-8859-1?Q?Symbian C++_deuxi=E8me_candidat_qui_me_para=EEte?=
=?ISO-8859-1?Q?xcellent?=
X-Priority: 1
Date: Mon, 2 Jun 2008 10:26:44 +0530
References: <55FA9B47-86E4-477D-B585-32870D2DEC16@inforill.com>
X-Mailer: Apple Mail (2.919.2)


--Apple-Mail-3--313351
Content-Type: text/plain;
charset=ISO-8859-1;
format=flowed;
delsp=yes
Content-Transfer-Encoding: quoted-printable

Salut Name2,

intel mini 1.83 GHz Intel Core Duo, Mac OS X (10.5.2), Apple Mail Version 3.2 (919/919.2) IMAP Account

Posted on Jun 5, 2008 4:49 AM

Reply
10 replies

Jun 5, 2008 8:34 PM in response to BDAqua

Spamhaus gave me this:

<========
IP Address range is listed on the Policy Block List (PBL)

Outbound Email Policy of The Spamhaus Project for this IP range:

This IP range has been identified by Spamhaus as not meeting our policy for IPs which should deliver 'direct-to-mx' mail to PBL users.

Important: If you are using any normal email software such as Outlook, Entourage, Thunderbird, Apple Mail, and you are being blocked by this Spamhaus PBL listing when you try to send email, the reason is simply that you need to turn on "SMTP Authentication" in your email software settings (Tools : Accounts : Properties : Outgoing Mail Server : check "My server requires authentication").
If you do not know how to do this, ask your Internet Service Provider for help with "SMTP Authentication".

========>

I am using IMAP with Apple Mail 3.2
I have set it up with SSL SMTP Authentication for gmail but the problem persists.
smtp.gmail.com
Server port 587
Use SSL turned on
Authentication: Password
UserName + Password supplied

Can you help me understand what the problem could be in the SMTP settings?

- MN

Jun 6, 2008 3:15 AM in response to dabcap

PERM_FAILURE: Gmail tried to deliver your message,


I missed this originally -- that you are sending from your Mac to/through a GMAIL SMTP server. Some of those servers are listed in some realtime blackhole lists as being addresses listed in SPAM TRAP systems.

This is one of the problems in using free email relays.

Can you send your email through another mail relay, such as your ISP's?

-fred

e-mail bouncing PERM_FAILURE message content rejected for policy reasons

Welcome to Apple Support Community
A forum where Apple customers help each other with their products. Get started with your Apple ID.