Outlook inserting multiple '@' characters in smtp message id

[Aleise Henry]

I have Outlook 2007 sp1, and I have an email account setup pointing at my
isp POP/SMTP server. When I send out email the SMTP Message-ID header
created by Outlook includes multiple @ characters which is invalid per RFC
822. In particular it gets marked as SPAM by spam detection engines.

Does anyone know how to get around this? Is it a bug in Outlook, or is there
something in the configuration that I've overlooked?

Code Sample:

Reply-To: (e-mail address removed)
From: "My Name" (e-mail address removed)
To: <[email protected]>
Subject: testt
Date: Mon, 31 Mar 2008 12:30:54 -0000
Organization: xxxxxxxx
Message-ID: <012301c889bd$18b3cd00$4a1b6700$@[email protected]>
MIME-Version: 1.0
Content-Type: multipart/alternative;
boundary="----=_NextPart_000_0124_01C889BD.18B3CD00"
X-Mailer: Microsoft Office Outlook 12.0
thread-index: AciJvRL2+wLvIbvzTWCpnZadQdnxsA==
Content-Language: en-gb
X-2020-Relay: Sent using blah-blah relay with auth code: xxxxx
Send Abuse reports to (e-mail address removed)
X-UIDL: SV9"!f-C!!Pc&#!17D"!

 

[Brian Tillman]

I have Outlook 2007 sp1, and I have an email account setup pointing
at my isp POP/SMTP server. When I send out email the SMTP Message-ID
header created by Outlook includes multiple @ characters which is
invalid per RFC 822. In particular it gets marked as SPAM by spam
detection engines.

I don't see anything wrong with your sample. Single "@" appear everywhere
except the Message-ID and it shouldn't matter there.

 

[Diane Poremsky {MVP}]

unless I'm blind, Section 3.6.4 (which deals with the message id) says
nothing about multiple @ AFAICS

"The message identifier (msg-id) itself MUST be a globally unique
identifier for a message. The generator of the message identifier
MUST guarantee that the msg-id is unique. There are several
algorithms that can be used to accomplish this. Since the msg-id has
a similar syntax to angle-addr (identical except that comments and
folding white space are not allowed), a good method is to put the
domain name (or a domain literal IP address) of the host on which the
message identifier was created on the right hand side of the "@", and
put a combination of the current absolute date and time along with
some other currently unique (perhaps sequential) identifier available
on the system (for example, a process id number) on the left hand
side. Using a date on the left hand side and a domain name or domain
literal on the right hand side makes it possible to guarantee
uniqueness since no two hosts use the same domain name or IP address
at the same time. Though other algorithms will work, it is
RECOMMENDED that the right hand side contain some domain identifier
(either of the host itself or otherwise) such that the generator of
the message identifier can guarantee the uniqueness of the left hand
side within the scope of that domain."


outlook uses the full email address on the right of the @ to guarantee
uniqueness, so you'll have 2 @'s.



** Please include your Outlook version, Account type, and Windows Version
when requesting assistance **

 

[Aleise Henry]

There is a section in RFC 822 that deals with multiple @ characters in an
address (section C.5.4 to be exact). I know this should have nothing to do
with the message id, but spam filters such as Spamassassin flag these
messages as 1.38 MSGID_MULTIPLE_AT Message-ID contains multiple '@'
characters and they are sometimes blocked. So I need to know if there is
some way to force Microsoft Outlook to guarantee uniqueness some other way.

Aleise

 

[Brian Tillman]

There is a section in RFC 822 that deals with multiple @ characters
in an address (section C.5.4 to be exact). I know this should have
nothing to do with the message id, but spam filters such as
Spamassassin flag these messages as 1.38 MSGID_MULTIPLE_AT Message-ID
contains multiple '@' characters and they are sometimes blocked. So I
need to know if there is some way to force Microsoft Outlook to
guarantee uniqueness some other way.

You cannot alter how Outlook creates the Message-ID header.

 

[Diane Poremsky {MVP}]

Which section is it? (you can't change it. There was a know issue with
spamassain during the beta but spamassian fixed their software soon after
RTM AFAIK)



** Please include your Outlook version, Account type, and Windows Version
when requesting assistance **

 

[Robin East]

Diane, your quote from RFC 2822 says that the message id syntax is
'angle-addr'. The definition given in 2822 is (s3.4):

[CFWS] "<" addr-spec ">" [CFWS] / obs-angle-addr

in essence this boils down to :

"<" addr-spec ">"

addr-spec is defined as:

local-part "@" domain

local-part and domain should both be 'dot-atom' (unless they are
'quoted-string's which the Outlook is not using) and these explicitly
exclude @-sign (it's a 'special'). RFC2822 would seem to allow multiple-@
signs for the message-id in the way Outlook does.

From what I can see this is a bug. Either microsoft should provide a patch
or maybe there is some deep down parameter that can be used to unset this
behaviour; from what I can see from trawling the internet this was
introduced as part of Outlook 2007.

This might seem somewhat semantic but I suffer from the same issue myself
for my business. I have had important email being treated as spam by some of
my clients - this is both disruptive and embarassing.

url:http://www.ureader.com/msg/10768342.aspx

 

[Robin East]

Multiple @ are not permitted in the message-id when you are using the syntax:

"<" addr ">"

(which is what Outlook 2007 is using). This is the case for both RFC822 and
RFC2822

Robin

 

[Robin East]

so to be slightly more challenging - I think both Diane and Brian are wrong
in the assertion that multiple @ in the msgid are OK. This looks like a bug
in Outlook.

Robin