Email — the convenience of sending a message (or spam) at the click of a button. No matter what anyone says, it’s certainly part of our daily (work) life.

While it’s a huge convenience for many of us, it can also cause massive headaches (like when your mailbox is completely full and you need to send an urgent document). Well, talk about the mother of all migraines…

According to Portfolio.com, a lawyer from Pepper Hamilton (which represents Lilly) intended to send a confidential document relating to the Zyprexa settlement to a co-counsel at Sidley Austin (another law firm) via email.

Unfortunately, instead of sending the email to Bradford Berenson (the co-counsel), she accidentally sent it to Alex Berenson instead, presumably due to the ever-so-convenient auto-complete function that most email programs have. And, as bad luck would have it, the Alex (as opposed to the Bradford) turned out to be a NY Times reporter, who then broke the story and caused a frenzy at Lilly.

…one of Eli Lilly’s lawyers at Pepper Hamilton in Philadelphia wanted to email Sidley Austin’s Berenson, about the negotiations. But apparently, the name that popped up from her email correspondents was the wrong Berenson… Alex Berenson logged on to find an internal “very comprehensive document” about the negotiations, the consultant said, and on January 30, Berenson’s article, “Lilly in Settlement Talks With U.S.” appeared on the Times’ website. A similar article followed the next day on the front page of the New York Times.

Ina Fried at News.com had some good commentary about this and also some helpful hints for customizing Outlook, in case you’re worried about this happening to you:

…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.

Email: you can’t live with it and you can’t live without it! Sigh…

BTW, if you want a more detailed opinion piece on this, read Erik Starkman’s article on the Starkman & Associates blog.