There is a great e-mail "horror story" on law.com today, about a friendly, helpful auto-complete function in a lawyer's e-mail software that resulted in his disqualification from a Federal case and an assessment of $40,000 in fees and costs.
The title is "E-mail 'Oops' Ends With General Counsel Being Booted From Case," and the article has a link to the order of court that results.
Important safety tip: Read everything in an outgoing e-mail, even the addresses.
One lawyer whom I know makes it a habit to save an outgoing e-mail as a draft, do something else, and come back to it an hour later. He doesn't win prizes for faster-than-light responses, but he avoids some embarrassing faster-than-thought mistakes.
Read more on the Walker Clark Worldview Blog.