05 March 2011

Pesky winmail.dat with Outlook, Apple Mac OS X Mail and me.com IMAP folders

I use me.com's IMAP folders to file email as part of an inbox zero policy I inflict on myself.  I recently had to resume using Exchange 2010 based email, but unfortunately not (yet!) directly connected to Apple Mac OS X Mail.  To access the Exchange mail, I've elected to use Outlook inside a Windows 7 VM.  I then hooked in my me.com IMAP folders into Windows Outlook so the Exchange and me.com folders are side by side in Outlook.  I then added an Outlook rule to copy new email that hits my Exchange Inbox to a me.com's Inbox.

This worked ok until I opened my first message in OS X Mail that had an attachment.  Instead of a normal attachment, I instead found a "winmail.dat" file.  Funny, I'd not seen one of those in a long time.

After some digging, I came across two ways to deal with the winmail.dat attachment problem:

1. The first and not recommended choice is TNEF's Enough.  The price is right at free/donations.  However, it's usability is awkward as you are required to open the *.dat file in a separate application that unpacks the TNEF format file from Exchange/Outlook and gives you the option to save the file.  I tried it, too painful.

2. The second and recommended choice is Letter Opener.  It is between USD 30-50.  It is seamlessly integrated with OS X Mail so you don't ever see a *.dat file, you see the attachments as you would in Outlook.

So if you stumble on this problem and need to consider TNEF's Enough versus Letter Opener, I'd recommend Letter Opener.

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