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Help winmail.dat

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TNEF is proprietary and used by Microsoft Outlook. It's associated with their Rich Text Format and isn't always understood by other clients all the time.

info here:
Outlook is sending winmail.dat attachments to Internet addresses

be sure to read the article before you do anything.

from the last part of the article:

If all else fails...
If nothing seems to be working and you use Outlook 2007 SP2, you can use a registry value to end TNEF encoding once and for all. This will affect your ability to use features that require TNEF encoding - Voting and Meeting Requests in native Outlook format.
  1. Close Outlook 2007
  2. Start Registry Editor (type regedit in the Start Search box or Start menu, Run command and press Enter)
  3. Locate the following registry key:
    HKEY_CURRENT_USER\Software\Microsoft\Office\12.0\Outlook\Preferences
  4. Add a new DWORD named DisableTNEF.
  5. Double click on DisableTNEF and in the Value data box, type 1
Other things to check would be the settings for removing unnecessary HTML data, to reduce the file size, and the encoding.

BTW, having read through most of the threads on this topic, I have ot say that Macs can send in RTF from Outlook too. :D
 
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