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Emails incorrectly converted to plain text when sent to external domains

Posted on 2009-06-30
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Last Modified: 2012-05-07
Yesterday I was added as a user to a client's Exchange server. I configured Outlook 2007, set up a signature and sent a test email to my address outside of their domain. It was sent in plain text. Checked my web mail just to be sure it was not an Outlook setting. It was plain text there as well.

Then I sent the same message to my new address. It was delivered in HTML.

I tested through Outlook Web Access as well as with another email address outside of their domain. Same results.

It appears that emails sent from this account to external domains (at least the 2 I tested with) are converted to plain text.

My client is at a loss to explain this. Emails sent from his account work just fine. I have received many with embedded screen shots, etc.

He can't find any settings that would override the mail format for a single mailbox.

There must be something different about my account. Any ideas?
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Question by:JohnDesautels
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Alan Hardisty earned 500 total points
ID: 24746803
Drop me an email (via my profile) and I'll tell you how it comes through.  There should be no reason for this, other than the receiving mail server converting it.
Also, check your Outlook settings (Tools, Options, Mail Format, Compose in this Message Format - make sure it says HTML).
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by:JohnDesautels
ID: 24746868
Tests have been sent.

Thanks!
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by:Alan Hardisty
ID: 24746905
And duly received as HTML format.
I also replied as HTML, so you should see what I received.
Seems to be your other mail servers converting the mail on your behalf.  Best give them a call and ask them to investigate.
Alan
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by:JohnDesautels
ID: 24747498


Alan,
I did a bit more testing.

When I sent an HTML message to an alias (info@domain.com) that points to the same email account (John@domain.com) it comes in as HTML. Same thing when I sent it to a different mail box on my same domain. Seems to rule out the ISP as the problem.
 
Looking at the headers there is a difference:  
 This is part of the header from the message that was received in HTML.
This is at the very bottom of the header.
X-MS-TNEF-Correlator:
acceptlanguage: en-US
Content-Type: multipart/alternative;
boundary="_000_164BEDC372BC5B4FBD56702AA4CA2BEE0F1EF81949[xxxx]"
MIME-Version: 1.0

This is part of the header from the plain text message.
This is between Received and From sections:
Content-Type: multipart/mixed;
 boundary="_000_164BEDC372BC5B4FBD56702AA4CA2BEE0F1EF81949[xxxx]"
 
 This is at the very bottom:
Accept-Language: en-US
Content-Language: en-US
X-MS-Has-Attach:
X-MS-TNEF-Correlator: <164BEDC372BC5B4FBD56702AA4CA2BEE0F1EF81949@[xxxx].com>
acceptlanguage: en-US
MIME-Version: 1.0  
 
Not sure if the placement of the tags, differences in the Content-Type or X-MS-TNEF-Correlator are significant or not.
Also just sent a test message to a buddy on yet a 3rd separate ISP. Plan text for him as well.
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by:Alan Hardisty
ID: 24750429
Have a read of the following which I came across whilst trying to resolve another Plain Text / HTML problem in the opposite direction!
http://support.microsoft.com/kb/821750
What are your settings for Message Format on the server set to?
Alan
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Expert Comment

by:Alan Hardisty
ID: 24750470
Sorry - an Exchange 2007 link here:
http://technet.microsoft.com/en-us/library/aa997208.aspx 
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Author Comment

by:JohnDesautels
ID: 24751029
I have asked the client for a screenshot of those settings.
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Author Comment

by:JohnDesautels
ID: 24753077
Here it is:
   

Properties.PNG
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Expert Comment

by:Alan Hardisty
ID: 24753088
If you change the setting to Always Use (Exchange rich-text format) and test it again, does anything improve?
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Author Comment

by:JohnDesautels
ID: 24753119
I don't have access to the server, but will request that they test that.

Is the difference in the mail headers I noted yesterday in any way significant? Same email sent to two mailboxes on the same external domain arrive in different formats...or at least are interpreted in different ways.

Thanks.
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Expert Comment

by:Alan Hardisty
ID: 24753219
It is highly likely that the messaging system on the receiving end is not Exchange and thus may not be able to interpret properly, the HTML email.
You have sent a email to me and I use Exchange and it came through in HTML.  You may need to check with your outside email provider to see if this is an issue that they can address as you are clearly sending HTML and thus the problem is not at your end.
Read the following - they are quite useful.
http://technet.microsoft.com/en-us/library/aa998896(EXCHG.65).aspx
http://www.freesoft.org/CIE/RFC/1521/18.htm  
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Author Closing Comment

by:JohnDesautels
ID: 31598306
Thanks for the tips, Alan.

Never did find a solution. Just living with it for now.

John
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