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Hotmail and 552 Too many recipients

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liste at jordet

Oct 3, 2007, 1:46 AM

Post #1 of 5 (4214 views)
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Hotmail and 552 Too many recipients

Hi,

I have a user which have a soccer contest going with his friends and
co-workers. They are now about 60 participants. For a couple of years he
have been sending out the results and standings to everyone
participating. This have worked great.

This weekend I got a mail from him, telling me he had got a mail from
"Mail Delivery System". I asked him to forward it to me (see below, some
email-addresses obfuscated to prevent the innocent).

He has all the recipients in the BCC field of his mailer (Thunderbird).
He used to have 14 hotmail recipients, but he added two new before he
sent this particular mail, and about 40-45 other recipients.

Two questions: 1) is the reason Hotmail now rejected his email that it's
suddenly 16 hotmail recipients instead of 14? I thought it must accept
at least 100 (although I know Hotmail isn't known to adhere to the
RFC's...) Perhaps it's because the recipients are in the bcc-field?
Maybe there is limits there?

2) Why did only six of the 16 Hotmail recipients fail? Oh, stupid me, I
just looked at the logs. It seems (logical enough) that when you use
bcc, it sends one and one recipient. Perhaps Hotmail doesn't like that?
Since it stops accepting mails after 10 recipients... (Weird it used to
work for 14 earlier...)

Other than the obvious "don't let your friends use hotmail", is there
anything I can do to avoid this?

Regards,
Stian

Emne: Mail delivery failed: returning message to sender
Dato: Fri, 28 Sep 2007 20:07:18 +0200
Fra: Mail Delivery System <Mailer-Daemon[at]buick.jordet.net>
Til: user1[at]mjohansen.net

This message was created automatically by mail delivery software.

A message that you sent could not be delivered to one or more of its
recipients. This is a permanent error. The following address(es) failed:

user2[at]hotmail.com
SMTP error from remote mail server after RCPT TO:<user2[at]hotmail.com>:
host mx1.hotmail.com [65.54.244.136]: 552 Too many recipients
user3[at]hotmail.com
SMTP error from remote mail server after RCPT TO:<user3[at]hotmail.com>:
host mx1.hotmail.com [65.54.244.136]: 552 Too many recipients
user4[at]hotmail.com
SMTP error from remote mail server after RCPT TO:<user4[at]hotmail.com>:
host mx1.hotmail.com [65.54.244.136]: 552 Too many recipients
user5[at]hotmail.com
SMTP error from remote mail server after RCPT TO:<user5[at]hotmail.com>:
host mx1.hotmail.com [65.54.244.136]: 552 Too many recipients
user6[at]hotmail.com
SMTP error from remote mail server after RCPT TO:<user6[at]hotmail.com>:
host mx1.hotmail.com [65.54.244.136]: 552 Too many recipients
user7[at]hotmail.com
SMTP error from remote mail server after RCPT TO:<user7[at]hotmail.com>:
host mx1.hotmail.com [65.54.244.136]: 552 Too many recipients

------ This is a copy of the message, including all the headers. ------

Return-path: <user1[at]mjohansen.net>
Received: from localhost ([127.0.0.1]:36020)
by buick.jordet.net with esmtp (Exim 4.67)
(envelope-from <user1[at]mjohansen.net>)
id 1IbK98-0004Wt-G1; Fri, 28 Sep 2007 20:01:02 +0200
Received: from 40.80-202-18.nextgentel.com (40.80-202-18.nextgentel.com
[80.202.18.40]) by webmail.jordet.net (Horde MIME library) with HTTP; Fri,
28 Sep 2007 20:01:00 +0200
Message-ID: <20070928200100.empiziae74kwk8og[at]webmail.jordet.net>
Date: Fri, 28 Sep 2007 20:01:00 +0200
From: Lars-Morten Johansen <user1[at]mjohansen.net>
To: user1[at]mjohansen.net
Cc: user8[at]start.no
Subject: 21 runder spilt
MIME-Version: 1.0
Content-Type: text/plain;
charset=ISO-8859-1;
DelSp="Yes";
format="flowed"
Content-Disposition: inline
Content-Transfer-Encoding: quoted-printable
User-Agent: Internet Messaging Program (IMP) H3 (4.1.4)
X-Virus-Scanned: ClamAV 0.91.2/4420/Fri Sep 28 17:43:46 2007 on
buick.jordet.net

[message snipped].

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exim-users at adam-barratt

Oct 3, 2007, 2:56 AM

Post #2 of 5 (3526 views)
Permalink

Re: Hotmail and 552 Too many recipients [In reply to]

Hi,

Stian Jordet wrote:
> I have a user which have a soccer contest going with his friends and
> co-workers. They are now about 60 participants. For a couple of years
> he have been sending out the results and standings to everyone
> participating. This have worked great.
[...]
> Two questions: 1) is the reason Hotmail now rejected his email that
> it's suddenly 16 hotmail recipients instead of 14? I thought it must
> accept
> at least 100 (although I know Hotmail isn't known to adhere to the
> RFC's...) Perhaps it's because the recipients are in the bcc-field?
> Maybe there is limits there?
>
> 2) Why did only six of the 16 Hotmail recipients fail? Oh, stupid me,

We had exactly this problem recently - the magic threshold appears to be 10
recipients. Delivery to the first nine recipients of a message succeeds, the
tenth and subsequent fail.

The solution I came up with is to set max_rcpt to nine or less on the smtp
transport delivering the mail to Hotmail. You could either do this globally
on your current transport (e.g. remote_smtp) or (as we did) create a copy of
the relevant router which only matches hotmail.{com,co.uk} and configure
that to use a copy of the transport but with max_rcpt set. Obviously the new
router should be placed before the existing one (assuming the current router
has domains=* or similar).

Hope that helps,

Adam

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leo at dicea

Oct 3, 2007, 3:11 AM

Post #3 of 5 (3490 views)
Permalink

Re: Hotmail and 552 Too many recipients [In reply to]

On 3 Oct 2007 at 10:46, Stian Jordet wrote:
> 2) Why did only six of the 16 Hotmail recipients fail? Oh, stupid me, I
> just looked at the logs. It seems (logical enough) that when you use
> bcc, it sends one and one recipient. Perhaps Hotmail doesn't like that?
> Since it stops accepting mails after 10 recipients... (Weird it used to
> work for 14 earlier...)
>
> Other than the obvious "don't let your friends use hotmail", is there
> anything I can do to avoid this?

Hotmail is evil. last week I had serious ploblem due their blacklisting one of
my servers. It used to return a 553 error saying that the message was
refused due smam on the message or previous contents.
Even writing to postmaster got the same result.
I wrote them in another way and after 2 days and considerable troubles for
some of their users they replied that it was becouse my server had no spf
records, and suggested me to put them.
Anyway the service worked again.
just for two days.
I wrote again, they replied with an empty message, and the service come
up again.
after one more day again the refuse, another letter from me, asking to tell
what was the message thet triggered their filter, to see if it was a my or their
fault.
They replied thet there was in past some block for spam from that server,
but currentry there is none ..
no information on how the server was blocked three times in one week !!!

--
Leonardo Boselli
Nucleo informatico e Telematico
Dipartimento Ingegneria Civile e Ambientale
Universita` di Firenze
Via Santa Marta 3
I-50139 Firenze
+39 055-4796-431
+39 348-8605-348
fax 055-495-333

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renaud at llorien

Oct 3, 2007, 4:10 AM

Post #4 of 5 (3487 views)
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Re: Hotmail and 552 Too many recipients [In reply to]

Leonardo Boselli wrote:
> On 3 Oct 2007 at 10:46, Stian Jordet wrote:
>> 2) Why did only six of the 16 Hotmail recipients fail? Oh, stupid me, I
>> just looked at the logs. It seems (logical enough) that when you use
>> bcc, it sends one and one recipient. Perhaps Hotmail doesn't like that?
>> Since it stops accepting mails after 10 recipients... (Weird it used to
>> work for 14 earlier...)
>>
>> Other than the obvious "don't let your friends use hotmail", is there
>> anything I can do to avoid this?
>
> Hotmail is evil. last week I had serious ploblem due their blacklisting one of
> my servers. It used to return a 553 error saying that the message was
> refused due smam on the message or previous contents.
> Even writing to postmaster got the same result.
> I wrote them in another way and after 2 days and considerable troubles for
> some of their users they replied that it was becouse my server had no spf
> records, and suggested me to put them.
> Anyway the service worked again.
> just for two days.
> I wrote again, they replied with an empty message, and the service come
> up again.
> after one more day again the refuse, another letter from me, asking to tell
> what was the message thet triggered their filter, to see if it was a my or their
> fault.
> They replied thet there was in past some block for spam from that server,
> but currentry there is none ..
> no information on how the server was blocked three times in one week !!!
>

This thread explains many things about hotmail:
http://lists.exim.org/lurker/message/20070610.175605.a1be972b.en.html

Attachments:

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liste at jordet

Oct 3, 2007, 4:31 AM

Post #5 of 5 (3435 views)
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Re: Hotmail and 552 Too many recipients [In reply to]

Renaud Allard wrote:
> This thread explains many things about hotmail:
> http://lists.exim.org/lurker/message/20070610.175605.a1be972b.en.html
>

While there is a lot of great hotmail information in that thread, it's
just about Hotmail eating your mail, this one was actually rejected at
smtp time.

Still, thanks for many great tips :)

-Stian

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