YouSendIt, MailBigFile and a host of other web services have popped up due to the simple fact that most email services won't let you send really large attachments. While Google upped its email attachment limit to 20MB this week, if you've got a 100MB file, you're still better off using a third party service.
But opening a browser window or tab and waiting for a file to upload just isn't that much fun (or reliable if you accidentally close the tab before your upload is done). YouSendIt recently released a beta version of a plugin for Outlook 2003 that will let you send large files almost as honest to goodness email attachment. No web browser required.
You can set Outlook to use YouSendIt for every file, to ask before sending every file, or for every file over a specified size. YouSentIt lets you send files up to 100MB for free, or if you have a paid account (starting at $5 per month), you can send files up to 2GB in size.
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