YouSendIt is one of the best-known services for moving large files from place to place – a persistent problem. I just learned about a way to set up Outlook to transmit large files through the YouSendIt service almost invisibly.

I’ve tried various things to dissuade people from attaching huge files to outgoing e-mail messages – coaching, gentle persistence, scolding, acts of violence, property destruction, mocking, cash payments, you name it. Nothing works. For all too many people, it’s not enough for a web service to be easy – it simply can’t require any change in habits at all.

YouSendIt has an Outlook plugin that comes close. Once installed, it intercepts an outgoing message with an oversized attachment after the “Send” button is pushed. The plugin moves the message to a special outbox, where the attachment is automatically uploaded to YouSendIt’s servers. The message is then sent with a link to where the attachment can be downloaded. The recipient can download the file with a single click. Here’s an FAQ with more details.

I love the idea. I’ve spoken to a couple of people who use it daily with no problems. (Secondhand anecdotes – your mileage may vary.) Theoretically it works with YouSendIt’s free service but if you’re considering it, you’re probably going to use it enough to justify the cost of a “Pro” account ($9.99/month) to get enough bandwidth and storage space. A serious business user can pay $29.99/month for a “Business Plus” account that removes all advertisements from both ends of the process and lets the company logo appear on the YouSendIt pages seen by the recipient. Here’s more info about the various levels of service from YouSendIt.

This might work well for busy lawyers and businesspeople who are dealing with huge PDFs and have no appetite for learning new tricks, as well as obviously being appealing for photographers and multimedia professionals. Good stuff!