Filed under: Software, Productivity
Letter Opener: new life for winmail.dat files

If you live in a world where you get email from Outlook users, and I think most of us do, you probably see the dreaded winmail.dat file on occasion. Outlook compresses all of its attachments together into one .dat file, leaving the rest of us scratching our heads as to what's inside. I've used TNEF'S Enough, a free utility for the Mac (mentioned last year by Mat) which will crack the files open for you. This week, however, I discovered Letter Opener.
Letter Opener is a Mail.app plugin which decodes the .dat files inline, so the process is transparent to you, the recipient. The attachments appear like any others, and life is that much easier. Letter Opener isn't cheap, and the utility vs. cost ratio is dependent on how many winmail.dat files you deal with on a daily basis. Prices range from $29.95US for a single license, to $179.95US for a 10-pack. More information and demo videos are available at the restoroot.com website.

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Reader Comments (Page 1 of 1)
peter said 9:27AM on 1-28-2009
Is that a joke?! $30 a seat?
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steve said 9:39AM on 1-28-2009
well... how often do you receive winmail.dat files? i never got one, so i guess it must be some rare case and therefore i think the price is acceptable for business users.
RobK said 9:40AM on 1-28-2009
The requirements are listed in a strange way on the website for Letter Opener.
Mac OS X 10.4.0 and later or
Mac OS X 10.3.0 and later
Does Letter Opener support Leopard?
Or is this capability to decode winmail.dat files built into Leopard Mail?
Rob
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Brett Terpstra said 9:44AM on 1-28-2009
Yes, I'm running it on Leopard right now, and no, Mail.app in Leopard definitely does not handle the .dat files natively. For me, they're a frequent enough pain that it's worth the expense, although I do think $30 is a high price point for a utility.
scott said 9:52AM on 1-28-2009
I run Microsoft Entourage 2004 and that mail program doesn't know what to do with them!
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jay said 10:10AM on 1-28-2009
If you use Google apps (GA) this doesn't work. The problem lies in Google's handling of the winmail.dat files. It reencodes them (or something like that). when the file is being retrieved from the server. So, a winmail.dat from Google doesn't open in Mail. However, going to the GA site and viewing your mail there Google has expanded the winmail.dat and you can see and download your files. It's messy.
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jay said 10:17AM on 1-28-2009
whoops... this is for IMAP not pop users.
Brandon Bohling said 10:49AM on 1-28-2009
I'm using a blend of Gmail, Google Apps, self-hosted domain email accounts all drawn into Mail.app. Since I do a lot of work with the PC world, I purchased Letter Opener about 9 months ago. I'd admit that it was rather difficult to justify an expense; however, it has been worth it...for me.
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pat said 10:44AM on 1-28-2009
the real fix for this is to have the sender modify the contact information they have for you to prevent sending mail in RTF, plain text or HTML should not encounter this issue.
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Brett Terpstra said 10:54AM on 1-28-2009
I beg to differ. That might work if it's a family member sending you the files, but if you have enough clients sending you winmail.dat files to make it worth investing in something to fix it, a transparent solution which avoids having to coax the average Windows business user to do anything even slightly technical is a far better fix.
Alan Fleming said 11:06AM on 1-28-2009
For occasional use, people might want to look at TNEF's Enough. It's a two step process (detach and drop) but it's $30 cheaper.
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Christopher said 12:36PM on 1-28-2009
TNEF's Enough only handles attachments in winmail.dat files (and does it only with short file names).
Letter Opener can additionally convert calendar events, address book entries, notes and nested messages.
sgmorr said 5:36PM on 1-28-2009
How serendipitous! I had a winmail.dat file that I received as an attachment yesterday (first time if I recall correctly) and I just somehow ran across this posting. I went the TNEF's enough route and it worked fine.
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