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The high cost of e-mail autocomplete

Beware the feature that tries to figure out who you are sending by the first few letters. It's not always right, as Eli Lilly found out the hard way.

I've always been leery of Microsoft Outlook's autocomplete feature. That's the one that guesses who you want to send the e-mail to by looking at the first few letters you type.

It's right most of the time.

But with e-mail used to send everything from jokes, to family photos to corporate secrets, "most of the time" seems like far too low a bar.

Eli Lilly and its outside lawyers found out this the hard way this week when one of the esquires sent a note intended for a colleague to a New York Times writer with the same last name. (Note: I'm not certain which e-mail program the lawyer was using, and it's supposition, though a seemingly safe bet, that some sort of autocomplete was to blame.)

The result was that confidential negotiations with the government involving as much as $1 billion quickly became nonconfidential. The Times, doing what it does, got a big scoop.

A representative for Pepper Hamilton, the law firm whose barrister sent the note, was not immediately available for comment. But, in good news for the firm, an Eli Lilly representative told Portfolio that the firm is not immediately getting the boot.

Still, that's some pretty big consequences for a feature that saves a few seconds' time. Sure, those seconds add up over time. But I imagine the lawyer in question would give any amount of time to have that e-mail back.

I try to always give my address bar a second look before hitting send, but once or twice have found my note to a colleague going to an outside contact with a similar name. Maybe Microsoft should get rid of the feature.

Then again, in a world where businesses and governments are increasingly secretive, maybe the typo has become the greatest opportunity for openness and democracy. On second thought, leave it in there.

Update: A Microsoft representative said the feature can be turned off. Here's how:

• Under the Tools menu, click Options.

• On the Preferences tab, click E-mail Options, and then click Advanced E-mail Options.

• Select or clear the "Suggest names while completing To, Cc, and Bcc fields" check box.

Another suggestion comes from ClearContext VP Brad Meador, who recommends people tweak Outlook settings to delay sending e-mail for a matter of minutes. That way there's a chance to catch a broad array of mistakes before they go out forever.