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In response to your manager's latest nagging e-mail, you write your office buddy a scathing critique of the boss's grammar, tacky shirts and bad breath - and then accidentally hit "Reply All."

After viewing your cousin's vacation photos online, you e-mail "Looks like she still hasn't lost that baby weight" to your sister - but you hit reply instead of forward, and now your cousin hates you.

E-mail disasters like this are the equivalent of 10-car pileups on the highway: preventable, common and messy.

For those who wreak havoc with a click of the send button, as one Ontario government employee did last week, netiquette experts say there is only one course of action: Beg forgiveness.

"All you can do is grovel. Say, 'I sincerely apologize, and I throw myself on your mercy,' " says Judith Kallos, author of E-mail Etiquette 101. "I hope you like the taste of humble pie."

Ontario cabinet staffer Aileen Siu and her bosses have recently swallowed a heaping helping.

In response to an e-mail from a young black man who'd applied for a job, Ms. Siu wrote: "This is the ghetto dude that I spoke to before." Instead of sending it to a co-worker, as she apparently intended, she sent it to the job seeker, Evon Reid.

The apology chain started with Ms. Siu, then quickly worked its way up to her boss (who emphasized that she was a part-time, contract worker), her boss's boss, and finally Ontario Premier Dalton McGuinty, who called Mr. Reid on Sunday to apologize personally.

Ms. Siu committed a double foul, experts say: Unprofessional, racist language in an e-mail is wrong no matter who the intended recipient is; and e-mailing the wrong person compounds the error.

"On the preventative side, people should not be committing to e-mail this kind of tone and language," says Christina Cavanagh, a professor at the Richard Ivey School of Business and author of Managing Your E-mail: Thinking Outside the Inbox.

"E-mail is not a conversation, it is a written record," she says. "We need to learn that e-mail is a resource to be feared and respected, not just something we slap together."

So, consider your words carefully, even if you're writing to a friend.

Think about how they'd look written in a formal letter, submitted as evidence in a lawsuit, forwarded around the Internet or featured in a newspaper headline.

And before you hit send, check and recheck the "To" and the "CC" fields. Realizing you've e-mailed the wrong person "is like closing the car door and seeing your keys inside just as it closes," says Bruce Snow, a partner in the Halifax-based human resources firm Robertson Surrette, who has set up a three-minute delay on his e-mail's send function.

Once the e-mail has been sent, the damage is usually done. If the recipient hasn't opened the e-mail yet, some systems allow you to retract what you've sent. But don't count on it. Others just send a notification e-mail telling the recipient to disregard the previous e-mail - which probably just serves to pique interest in the message.

When it's time for damage control, make your apology in person, or at least on the phone - not by e-mail. Own up to what you wrote, Mr. Snow says, even if it was ugly. For example, if you complained about your boss, be prepared to explain respectfully why you're unhappy with his or her leadership. That is, if you still have a job.

"It's disingenuous to disavow the sentiment you were expressing," Mr. Snow says. "You're going to have to take your lumps. You'll probably add insult to injury if you try to deny it."

Even when people know the rules of careful e-mailing, mistakes happen.

Brad Henderson, a Canadian who lives in Jalisco, Mexico, recalls an e-mail he sent while en route to a conference-planning meeting in Sao Paulo, Brazil. He fired off a note to the event planner, Sergio, and got a response asking for more details.

"I couldn't believe that he could have forgotten about this meeting and I provided him with a quick overview," Mr. Henderson said in a (polite and carefully worded) e-mail interview.

When he arrived, Sergio was waiting for him - but it was the wrong Sergio. This Sergio was an important Sao Paulo business contact who was mystified about why he'd been summoned across town at rush hour.

"I sat down with Sergio number two, explained my terrible error and begged forgiveness," Mr. Henderson wrote. "Begging was my only option and begging in my bad Portuguese was especially pathetic."

Although he followed the experts' advice, Mr. Henderson isn't sure whether the grovelling worked.

"I don't know about the apology," he wrote. "I will see if he returns my e-mail or calls when I am there in September."

globeandmail.com/life

Avoid e-mail disasters - or, at least learn how to recover from them. Judith Kallos, author of E-mail Etiquette 101 and creator of NetManners.com will be online at 11 a.m. EDT to take your questions.