Error 550 Messages should have one or no Date headers, not 2

I would like to report an important technical issue. Please don't reply with a copy-pasted text.

Here is the issue when using connected external accounts:

This is a permanent error. The following address(es) failed:
(email)
    host outbound.mailspamprotection.com [IP]
    SMTP error from remote mail server after end of data:
    550 Messages should have one or no Date headers, not 2.

On top left i see Outlook Email
(https://outlook.live.com)

Here is a LIST of others having the EXACT SAME ISSUE FOR A MONTH OR MORE:

http://answers.microsoft.com/en-us/outlook_com/forum/oemail-osend/sending-error-550-messages-should-have-one-or-no/17979b92-063a-45c2-b332-65157f173e8c

Please fix, this is URGENT...

having exactly the same issue since today

i try to send mail with a connected account, logging in to a 3rd party smtp-server

the rejected mail-message actually contains two "Date:" headers and funny enough one of these two mixed up the month and day (Date: May, 10 2016)

perhaps that is the cause: software looking for a Dateheader in the correct format "October, 5 2016", not finding and adding a second Date header

Return-Path:

I too have recently had my Outlook.com account upgraded to the new outlook ('Outlook E-mail' in top left corner) and immediately encountered the same problem with every send bouncing with errors saying:

SMTP error from remote mail server after end of data:
    550 Messages should have one or no Date headers, not 2.

Like others I have checked with any other ISP involved and all point to the change in the Outlook.com that has been made.

I did note though that the extra date added is the first one in the message properties together with an additional header.  This date is also being interpreted as a USA date format (MM/DD/YYYY) rather than the original UK date format (DD/MM/YYYY).  The IP addresses given as originating IP address in these headers are 157.56.255.156 and 40.101.6.5, which are both showing on IP lookup as United States IP address with no further info.  My ISP is UK based and neither IP address is related to them.

I have given the message headers below.  I have also tried change the location and date format on my PC and in my Outlook account to being English (United States) but still get the error.

Yes I have tried removing/adding the connected account in Outlook.com and removing/adding the Outlook 2016 email account.

I have also discovered my rules are not being processed now I am on the new Outlook.com - my rules are in Outlook.com and yes I have tried removing and re-adding them!!  But will search for or create other topic for that.

Like others this is giving me serious doubts about the use of Outlook.com and whether Microsoft are competent in managing this service!

Message Headers:

X-Originating-IP: [157.56.255.156]

X-Spam: 0
X-Authority: v=2.1 cv=XKnNMlVE c=1 sm=1 tr=0 a=wzbBplmuQq/qNDFe4AHscQ==:117
 a=L9H7d07YOLsA:10 a=9cW_t1CCXrUA:10 a=s5jvgZ67dGcA:10 a=MKtGQD3n3ToA:10
 a=dik7HMQjudEA:10 a=ZZnuYtJkoWoA:10 a=UqCG9HQmAAAA:8 a=v1xsnL4xAAAA:8
 a=L1DgeVckAAAA:8 a=LQ2z_tjo71EVGt7SHOQA:9 a=prZj-HPlkExr_8bm:21
 a=G-irWj2FY3-m3f0e:21 a=CjuIK1q_8ugA:10 a=WcJu8R9JZH0A:10 a=yMhMjlubAAAA:8
 a=SSmOFEACAAAA:8 a=J9WeFX6PC2sOgm-lNpsA:9 a=VtHPxupRMWuYYAuF:21
 a=HyK23dXTHKs70DIj:21 a=-dFS6pPvnFioJ--X:21 a=gKO2Hq4RSVkA:10
 a=UiCQ7L4-1S4A:10 a=hTZeC7Yk6K0A:10 a=frz4AuCg-hUA:10
 a=XqhbnV00hwtEhPrFMTfD:22 a=TN0B2Mp5y4gnXXUa0s3J:22 a=nejRm8QsiXWwDM9pz4hE:22
 a=BKKCjISod1eDJeS0ORpz:22 a=zjWhRoSqWz9hl55Hdlzg:22
Date: Sat, 10 Dec 2016 09:56:32 +0000
From: "xxxxxxxxxxxxxxxxxxxxxxx"
To: yyyyyyyyyyyyyyyyy <*** Email address is removed for privacy ***>
References: <*** Email address is removed for privacy ***> <*** Email address is removed for privacy ***>
In-Reply-To: <*** Email address is removed for privacy ***>
Subject: FW: Document and spreadsheet to start QA work on Emails for IRRI
Date: Wed, 12 Oct 2016 10:56:32 +0100
Message-ID: <001801d2246e$e9a54290$bcefc7b0$@ourbrian.co.uk>
Content-Type: multipart/alternative;
boundary="----=_NextPart_000_0019_01D22477.4B72F960"
X-Mailer: Microsoft Outlook 16.0
Thread-Index: AdIj6lXQIYaibbs8Eic72bA6c+lCkQACPciaAB7jaOA=
Content-Language: en-gb
MIME-Version: 1.0


First Date:
10 Dec 2016 09:56:32 +0000 = 12/10/2016 09:56:32 +0000 USA Date System MM/DD/YYYY

Second Date:
12 Oct 2016 10:56:32 +0100 = 12/10/2016 10:56:32 +0100 UK Date System DD/MM/YYYY


This was the same with an email sent on 11/10/2016 (UK Date System DD/MM/YYYY) where the First Date showed 10 Nov 2016 and Second Date showed 11 Oct 2016

And is supported by the following message header as well.

X-Originating-IP: [40.101.6.5]
X-Spam: 0
X-Authority: v=2.1 cv=OPLapnuB c=1 sm=1 tr=0 a=Dq9xvRxb75zbvUV0W85BLA==:117
 a=Dq9xvRxb75zbvUV0W85BLA==:17 a=L9H7d07YOLsA:10 a=9cW_t1CCXrUA:10
 a=s5jvgZ67dGcA:10 a=MKtGQD3n3ToA:10 a=ZZnuYtJkoWoA:10 a=dik7HMQjudEA:10
 a=L1DgeVckAAAA:8 a=xhwyluNhbBbH_RywpDwA:9 a=X-dTv53UJD4EGR6H:21
 a=nFdfBvKmHQx_LL0n:21 a=CjuIK1q_8ugA:10 a=CNcrymxtfm0A:10 a=WcJu8R9JZH0A:10
 a=yMhMjlubAAAA:8 a=SSmOFEACAAAA:8 a=AA_4__IIS0MDJvNRD0QA:9
 a=u4FCHFKUyqsxsqzC:21 a=oBeHB4xxJPXTpgc2:21 a=782EXV2sG_MYxlQk:21
 a=gKO2Hq4RSVkA:10 a=UiCQ7L4-1S4A:10 a=hTZeC7Yk6K0A:10 a=frz4AuCg-hUA:10
 a=HzzenLwr6KiCRalptDgA:9 a=IKIoO-ieCDEA:10 a=uP1S8zI-UHbOJ-WjAZQA:9
 a=nejRm8QsiXWwDM9pz4hE:22 a=BKKCjISod1eDJeS0ORpz:22 a=zjWhRoSqWz9hl55Hdlzg:22
Date: (invalid)
From: "xxxxxxxxxxxxxxxxxxxxxxx" <live@xxxxxx>
To: yyyyyyyyyyyyyyyyy <*** Email address is removed for privacy ***>
References: <000001d219b5$5f2f8350$1d8e89f0$@eco-consultants.co.uk> <002801d21a16$e19ad8b0$a4d08a10$@eco-consultants.co.uk>
In-Reply-To: <002801d21a16$e19ad8b0$a4d08a10$@eco-consultants.co.uk>
Subject: Invoice and Timesheet for Q3 2016
Date: Fri, 30 Sep 2016 13:53:43 +0100
Message-ID: <008001d21b19$ad201920$07604b60$@eco-consultants.co.uk>
Content-Type: multipart/mixed;
boundary="----=_NextPart_000_0081_01D21B22.0EE67CF0"
X-Mailer: Microsoft Outlook 16.0
Thread-Index: AdIZtRSElizS5maXmy3rUwtzlpBV6gAYbraAAEC0bIA=
Content-Language: en-gb
MIME-Version: 1.0


First Date:
(invalid) as in the USA Date System 30/09/2016 12:53:43 +0000 No month 30!!

Second date
Fri, 30 Sep 2016 13:53:43 +0100 = 30/09/2016 13:53:43 +0100

I saw this Invalid date issue in at least one of the returned emails. But I couldn't replicate exactly. So I dug some more. I used a tool (which had helped me fix some email configuration issues earlier) www.mail-tester.com [note - I just discovered through the below testing there is a small charge for this service if you do more than 3 tests per day. Sorry, it used to be free. But I paid anyway to discover the below.]

This told me my DKIM, SPF, HELO were all valid and that I had an Invalid Date because the header was not RFC 2822 compliant! Thanks, Microsoft.

The info link referenced http://wiki.apache.org/spamassassin/Rules/INVALID_DATE

"This suggests the sender is using a badly-written mailout program rather than a regular email client. "

So evidence pointing to the new version of Outlook.

As it happens, I have an old not-yet-migrated Outlook as well as a newly-migrated one. Both have the original Outlook emails and both have external addresses. These are called Added in old Outlook and Connected in new Outlook. I can confirm the Date Header RFC 2822 non-compliance is solely with Connected accounts in new Outlook.

1. old Outlook main email - no header issue

2. old Outlook Added account - no header issue

3. new Outlook main email - no header issue

4. new Outlook Connected account - Invalid Date: header not RFC 2822

By the way, I run the same mailservers for both the Added account in 2 and the Connected account in 4 so I know they are configured the same. [edited to add tests 5 and 6]

So that reminded me I have a webmail system on my mailservers so I used the same accounts as in 2 and 4 above to test from there:

5. the same account as Connected to new Outlook - no header issue

6. the same account as Added to old Outlook - no header issue.

It's a Microsoft issue for sure - it's how they handle Connected accounts in the new Outlook.

HTH, Mike

Adding my voice to this issue. I have the exact same problem outlined. 

Since being forced to use the new Outlook.com, my connected email account cannot successfully send emails because of the non-compliant date header. 

Please fix this, or let users revert to the older version of the software.

Same here!

See also my thread:

http://answers.microsoft.com/en-us/msoffice/forum/msoffice_outlook-mso_win10/sending-via-office-outlook-client-550-messages/14898492-1a6f-420e-9365-b1e9200e781d

Please solve quickly!

Hello,

I have sent a Private Message regarding your concern.

We are looking forward to your response.

How do I read the private reply?