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Evade e-mail exasperation

By Christopher Breen , Macworld , 04/30/2008

If you're like 99.7% of computer users, your e-mail client gets more of a workout than any other software you use. And given the amount of time you spend with this particular software, it's not surprising that minor annoyances you'd forgive in other programs become a Big Deal when you encounter them hour after hour, day after day. I've rounded up some common e-mail problems and provided solutions to help you keep them under control.

Decipher winmail.dat files

Most people who have used e-mail for longer than the lifespan of a fruit fly have received messages with winmail.dat attachments, which typically won't open on a Mac. The source of these files is Microsoft Outlook, Windows' omnipresent e-mail program. They're generated when an Outlook user on a PC formats the e-mail message (and any attachments) in Outlook's Rich Text Format (RTF). This is not the universal RTF we Mac users know and love; rather, it's a proprietary format that's compatible with Outlook but not with other e-mail clients. When an e-mail client other than Outlook receives the message, it finds the inscrutable winmail.dat files enclosed.

There are a couple of things you can do to get at the attachments. If you know the correspondent well enough to make the suggestion, ask that he or she send messages either as plain text or as HTML (Outlook offers both options). Either format works with the Mac (and with every other e-mail client in the universe), and attachments won't get mucked up.

Alternatively, you can deal with the issue by taking steps on your end. Just drop a winmail.dat file on a utility such as Josh Jacob's TNEF's Enough (free), for instance, and the utility will offer to extract the file's inner goodness. You can also try Christopher Atlan's Omic ($30), an Apple Mail plug-in that converts these files into their original, readable form, and identifies the attachments properly in a Mail message's attachments area. Note, however, that as I write this, neither of these utilities has yet been updated for Mac OS X 10.5 (Leopard).

Kick-start a sluggish e-mail client

If your e-mail client runs as slow as molasses, it's likely jammed with messages. Thankfully, you can speed things up by archiving old messages and then deleting the originals, and by stripping out old attachments.

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