Hotmail rejects html mail with attachment claims it is not RFC 5322 compliant

Same issue!

Only happen with Hotmail and MSN accounts like live.com etc... but Gmail accounts not reject the mail

Any ideas what can be the issue?

Can you tell if this was working with previous version like beta2 or beta1? That would narrow down the possibilities of where did this go wrong.

I just ran into a similar issue. I got an error saying that

SMTP error from remote mail server after end of data:
   host 246620674.pamx1.hotmail.com [65.54.188.109]:
   550 5.7.0 (BAY004-PAMC2F6) Message could not be delivered. Please ensure the message is RFC 5322 compliant.

I'm trying to setup Drupal Commerce so I can send html notification email. I admit it's difficult because there are a lot of moving parts to this setup.

Modules involved:

- message 7.x-1.9
- message_notify 7.x-2.5
- mailsystem 7.x-2.34
- mimemail 7.x-1.0-beta3

I have not tried other versions.
That being said, I'm running the same versions as a local Commerce Kickstart install and it has no problems sending html emails to the same recipient.

Any help would be appreciated.

Installed mimenail-7.x-1.x-dev.

Created a simple component using Rules with a single Send mail action.

Using the execute link, I made numerous tests (with/without 'Use simple address format '), no attachments. Same error from hotmail when the email of the recipient is Microsoft based.

If I change the recipient to a Gmail account, no error but Gmail thinks it's spam because (unknown sender) i.e. it doesn't see/get the email. When I forward this email to another account, this is what it looks like: From: <>. The from field is empty. Strange.

In Rules, if I set a value for the From field nothing changes: Gmail shows (unknown sender).

Quite frustrating...
Setting priority to Major.

@bisonbleu: You should investigate further why is the From header empty. By default the module sets this header field (if it is empty) to the site address.

Note that support requests should never be marked "critical" or "major".

You should investigate further why is the From header empty.

@sgabe, do you have any suggestions and/or pointers? I've been working on this issue for the past 2 days. Here's what I get back when I try sending an email.

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:

 bisonbleu@somedomain.com
   SMTP error from remote mail server after end of data:
   host 246620674.pamx1.hotmail.com [65.54.188.109]:
   550 5.7.0 (BAY004-PAMC2F8) Message could not be delivered. Please ensure the message is RFC 5322 compliant.

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

Return-path: <admin@adifferentdomain.com>
Received: from five9dev by s3-somecity.accountservergroup.com with local (Exim 4.82)
	(envelope-from <admin@adifferentdomain.com>)
	id 1XhHwt-000GEi-Pk
	for bisonbleu@somedomain.com; Thu, 23 Oct 2014 08:57:04 -0400
To: "=?UTF-8?B?VsOpbG9jZQ==?=" <bisonbleu@somedomain.com>
Subject: This is a mimemail test from a.dev.website
MIME-Version:1.0
Content-Type:multipart/mixed;
boundary="d4976ef0b64ad2f67d678ef6e4a90bea83b9ba221"
Content-Transfer-Encoding:8Bit
X-Mailer:Drupal
From:=?UTF-8?B?Ij0/VVRGLTg/Qj9VM2RwYzNNZ1EyRnVZV1JwWVc0Z1EyaGhiV0psY2lCdlppQkQ=?=
=?UTF-8?B?YjIxdFpYSmpaU0FvVVhYRHFXSmxZeWtnU1c0PT89CiA9P1VURi04P0I/WXk0PT8=?=
=?UTF-8?B?PSIgPGFkbWluQHJlbmF1ZGpvdWJlcnQuY29tPg==?=
Message-Id: <E1XhHwt-000GEi-Pk@s3-somecity.accountservergroup.com>
Date: Thu, 23 Oct 2014 08:57:03 -0400

This is a multi-part message in MIME format.

@bisonbleu, thank you for your quick response, from the provided information it is clear that the sender address is double encoded and the result is an invalid string.

If I am right this issue is a duplicate of #1908318: Sender is double encoded, please test the attached patch in #5 and possibly in #4 and report back there.

it is clear that the sender address is double encoded

Can you show me where & explain?

[update: answering my own question] - Note there is no email in the following paragraph.

From:=?UTF-8?B?Ij0/VVRGLTg/Qj9VM2RwYzNNZ1EyRnVZV1JwWVc0Z1EyaGhiV0psY2lCdlppQkQ=?=
=?UTF-8?B?YjIxdFpYSmpaU0FvVVhYRHFXSmxZeWtnU1c0PT89CiA9P1VURi04P0I/WXk0PT8=?=
=?UTF-8?B?PSIgPGFkbWluQHJlbmF1ZGpvdWJlcnQuY29tPg==?=

Patch mimemail-sender_is_double_encoded-1908318-4.patch fixes the (sender unknown) issue. Alleluia! :-)

Patch mimemail-2218037-5.patch does not. Here's what I get back.

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:

 bisonbleu@somedomain.com
   SMTP error from remote mail server after end of data:
   host 246620674.pamx1.hotmail.com [65.54.188.109]:
   550 5.7.0 (BAY004-PAMC2F3) Message could not be delivered. Please ensure the message is RFC 5322 compliant.

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

Return-path: <admin@adifferentdomain.com>
Received: from five9dev by s3-montreal.accountservergroup.com with local (Exim 4.82)
	(envelope-from <admin@adifferentdomain.com>)
	id 1XhInG-000ACu-NM; Thu, 23 Oct 2014 09:51:11 -0400
To: bisonbleu@somedomain.com
Subject: This is a mimemail test from a.dev.website
MIME-Version:1.0
Content-Type:multipart/mixed;
boundary="adfab6c1ce2c9e42fe2c13126fd38fb5078728d71"
Content-Transfer-Encoding:8Bit
X-Mailer:Drupal
From:=?UTF-8?B?IlN3aXNzIENhbmFkaWFuIENoYW1iZXIgb2YgQ29tbWVyY2UgKFF1w6liZWMpIEk=?=
=?UTF-8?B?bmMuIiA8YWRtaW5AcmVuYXVkam91YmVydC5jb20+?=
Message-Id: <E1XhInG-000ACu-NM@s3-somecity.accountservergroup.com>
Date: Thu, 23 Oct 2014 09:51:10 -0400

This is a multi-part message in MIME format.

@bisonbleu, please continue in #1908318: Sender is double encoded.