We have a customer who can only receive plain text emails, i have change the settings in outlook and email are sent ok, but if we add an attachment they receive it as a winmail.dat file.
I have changed the registry keys, cleared the cache, recreated the profile and ran the fix it tool.
The email is definitely being sent as plan text by the attachment shows as, Content-Type: application/ms-tnef; name="winmail.dat"