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weird work email problem

Speaking of work, here's a weird work-related problem that's been plaguing me for months.

I work regularly with my friend Tony, who is a Microsoft vendor and has a microsoft.com email address that he uses for work. I use my mac.com/me.com address for work.

When Tony uses the Microsoft Outlook application on his computer to send files to my mac.com address, I receive a single winmail.dat attachment that's apparently an archive of whatever files were included. I get this winmail.dat whether I'm using my Mail application on my laptop or the MobileMe web-based mail interface. However, I can't do anything useful with it, because neither the Mac nor Windows recognizes the .dat file as anything useable. And in any case, I clearly should not be getting this single .dat file when he sends me several separate files that were not archived.

When Tony uses the same Outlook application to send files to my Yahoo address, for example, they come through correctly.

When Tony uses Outlook Web Access to send files to my mac.com address, they come through correctly.

Tony is not having this winmail.dat problem when using the Outlook application to send files to anyone else.

We've just verified that other mac.com users can receive files correctly from him, too. (And Tony sent the test file using both the mac.com and me.com address of our test subject, so it's not a question of that being the issue.)

I'm not receiving winmail.dat attachments from anyone else, including other people using Microsoft email addresses; I haven't actually asked them yet to verify that they're using the Outlook application versus Outlook Web Access, but it seems unlikely that everyone else is always using OWA.

How could there be a problem specifically between Tony's Outlook client—and this is a freshly-installed one on a new machine, but the problem persists—and my mac.com address, but not any other combination?

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