Outlook users' problems with Apple mail attachments

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Outlook users' problems with Apple mail attachments

Folks on Windows XP using Outlook 2003 are having problems with email from Apple mail. Apple mail is using Windows Friendly Attachments and Rich Text as the settings. Sometimes attachments (Word, Excel, PDF) come in fine with an additional .htm attachment, but the body text of the message is missing. If the Outlook user opens the .htm file, there is the body of the Apple mail. Testing with Plain Text results in the body text appearing fine in Outlook, but the attachment is seen as a *.dat file and of course can't be opened. The Macs are all on OS X Tiger with all OS updates applied. Users of Outlook in other offices don't have this problem, and users of Thunderbird on Windows don't have this problem. Any ideas on what is causing this and how to resolve it? Is there a setting on Outlook that needs to be tweaked? Is there a setting on Apple mail that needs to be tweaked? Apple mail attachments to this Windows office worked fine until a few weeks ago. I do not know what changed between then and now as I am not in charge of the computers at the Windows office. Could a Mac OS update have caused a problem? Something on Windows or Outlook specifically? Thanks for any help you can provide. I've scoured the web and have tried everything to no avail. Zipping attachments, while a workaround, is not a long-term solution. Thanks!

various Intel Macs, Mac OS X (10.4.11)

Posted on Apr 9, 2009 12:14 PM

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Answer 1

a brody

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Apr 9, 2009 12:28 PM in response to LBUCB

Try sending it instead with plain text. Unfortunately nothing short of plain text is universally communicable via all e-mail clients.

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Answer 2

LBUCB Author

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Apr 9, 2009 12:33 PM in response to a brody

I've tried Plain Text and the body of the message came through fine, but it killed the attachment. It was a Word 2004 attachment, and it came through as a *.dat file. When using Rich Text, the attachment comes through fine (though with an additional .htm attachment), then the body text doesn't show up!

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Answer 3

a brody

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Apr 9, 2009 12:45 PM in response to LBUCB

Sounds like a problem on their end.

Instruct them to learn how to use webmail:

http://www.3wmail.com/ or http://www.mail2web.com/ offers a good alternative.

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Answer 4

LBUCB Author

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Apr 9, 2009 12:48 PM in response to a brody

That's what I've been thinking all along, but don't know how to "prove" it, nor what to recommend for that Windows office outside of webmail. They think the problem is on the Mac end. I think the problem is on their end. Don't want to get into any conflicts about this. 🙂

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Answer 5

LBUCB Author

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Apr 9, 2009 12:50 PM in response to LBUCB

Actually, if they check via the web and the body text and attachments look fine, then it would indicate a problem with Outlook, n'est-ce pas?

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Answer 6

a brody

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Apr 9, 2009 1:11 PM in response to LBUCB

It would indeed.

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Answer 7

LBUCB Author

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Apr 9, 2009 8:31 PM in response to a brody

Just found out the Windows person is using Outlook 2007 and was recently upgrade to that. So far can't convince them that the problem is on their end.

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Answer 8

a brody

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Apr 10, 2009 6:10 AM in response to LBUCB

Well tell them the problem only surfaced when they upgraded. Logically it must be on their end.

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Answer 9

LBUCB Author

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Apr 10, 2009 9:35 AM in response to a brody

Spoke to their Windows IT person and they are going to test with Thunderbird for Windows to see if there are problems with that. In the meantime, a Windows colleague of mine pointed out the following:
http://msdn.microsoft.com/en-us/library/aa338201.aspx for information about what may be going on.

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Answer 10

a brody

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Apr 10, 2009 9:41 AM in response to LBUCB

Since you are running 10.4.11, I have to wonder if 10.5.6's Mail application better supports the new CSS formatting. Is there any way you can try to send the same documents from an Apple Store and see if the formatting is different? That might at least let you know if it is worth while updating to 10.5.6 on a separate boot volume just for sending messages to these people. I wouldn't update to everything unless you have known applications that all will work with that operating system.

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Answer 11

LBUCB Author

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Apr 15, 2009 1:05 PM in response to a brody

Hi there,

Good suggestion. We did a test from a Leopard Mac with Apple mail and the recipient could see both the body text and attachments just fine. My Windows co-worker pointed me to this: http://msdn.microsoft.com/en-us/library/aa338201.aspx

It annoys me no end that it looks like MS changed something that lots of people are complaining about, including Windows users, and as a result, I now have to upgrade my clients to OS X Leopard, which wasn't in our plans for the immediate future. Sigh...

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Answer 12

a brody

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Apr 15, 2009 1:54 PM in response to LBUCB

Well just keep around a hard drive that is designed to boot a few machines into 10.5.6. If you have a mixture of Intel and PowerPC Macs, make sure that the partitions are designed to boot PowerPC and Intel separately. A procedure for doing that is described here:

http://www.macosxhints.com/article.php?story=2006061610374449

Firewire generally will only boot PowerPC machines, though Intel Macs you aren't limited to Firewire.

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Answer 13

LBUCB Author

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Apr 17, 2009 1:44 PM in response to a brody

Interestingly, it turns out that under Tiger, if you change the Text Encoding to Unicode (UTL-8) the attachments go through fine. We are still going to go with the plan to upgrade folks to Leopard, but it's still something I wanted to note.

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Answer 14

Apr 17, 2009 4:02 PM in response to LBUCB

Is this in an environment where an MS Exchange Server is being used? Seeing a file change to .dat would often point to that.

Plain Text should be the plan of action for users of Apple Mail, but something (probably the Exchange Server) is messing that up. See:

http://support.microsoft.com/kb/138053

and also related:

http://www.pchell.com/support/winmaildat.shtml

Moving to Leopard would probably not solve this -- the administrator of the exchange server must act.

Also the problem with winmail.dat files is known to impact other email clients used even on Windows computers.

Ernie

Message was edited by: Ernie Stamper

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Answer 15

WMTA

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May 14, 2009 2:50 PM in response to Ernie Stamper

Changing to the current version of OSX does not seem to affect this issue. When you have the confluence (effluence?) of Exchange server, vista and Office 07 the only way i have found to get attachments through every time is to zip them... and then spend some time trying to figure out how to tell a Vista user (which i ain't) how to get unzip to put the file on their desk top...
just shoot me.
I would welcome a workaround that takes into account the helplessness of vista users.
It may be their FAULT but when they are not tech-compatible and either partners in a transaction or clients... telling them it is their fault doesn't get it

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