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Experts reveal e-mail nightmares, safety tips

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  • Author shares embarrassing stories of e-mail sent to wrong person
  • "One click, and suddenly we'd lost a $5 million account," says publicist
  • Service called lets e-mailers tinker with or erase messages
  • Expert's advice: Type recipient's full name and never use reply-all
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By Anna Jane Grossman
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(LifeWire) -- Nancy Dunetz, who teaches English as a second language in New York City, sat down in the school staff room to check her e-mail. One of the messages in her inbox was from an acquaintance she'd been corresponding with since their 50th high school reunion last year.

In a survey of 4,000 people, about a third said they had accidentally sent an e-mail to the wrong person.

In a survey of 4,000 people, about a third said they had accidentally sent an e-mail to the wrong person.

But this e-mail last June didn't contain chummy banter or reminiscences. It simply included a lewd photo of a partly unclothed young man. The file name of the picture was "Mid East Hottie."

"I was shocked!" says Dunetz, 68. She hastily closed the e-mail and tried to erase the image from her mind.

Later that day, the sender e-mailed an apology to her and two dozen others who had received the e-mail. He explained he'd been experimenting with his new computer and was trying to figure out how to add attachments to an e-mail, Dunetz says. In doing so, he attached an image from his desktop and tried to send it to himself. Instead, the e-mail program automatically filled in an entire group from his address book -- something he apparently didn't realize until after he hit the "send" button.

"I felt terrible for him," Dunetz says. "I could imagine just how mortified he must have been."

With some 55 billion e-mails being sent daily (not including spam), according to e-mail archiving company The Radicati Group, misdirected e-mails have become the online equivalent of a wrong number. They're unavoidable, annoying -- and often embarrassing.

The 'uh-oh' e-mail

In a recent online survey conducted by AOL, 32 percent of the 4,000 respondents have at one time or another mistakenly forwarded an e-mail to an unintended recipient. And often, it's something not so nice.

Karla Comer, an account executive at an ad agency in Greensboro, North Carolina, knows just how embarrassing that can be. In 2004, Comer met a guy at a concert and went out with him a few times, but ultimately realized she wasn't interested. "He was just awkward and clumsy. And sometimes I'd catch him staring at me, which really creeped me out," she says.

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She tried to end the relationship by simply not returning his phone calls. "But then he e-mailed and casually said that he had not heard from me in a while and he hoped everything was fine but just assumed I was busy," says Comer, 31.

"Before I returned his e-mail, I sent the message to a close girlfriend with a blurb about what an idiot I thought he was and that dating him was a bad idea because he had no understanding of social cues."

She thought she sent the "he's an idiot" e-mail only to her girlfriend.

To her horror, Comer says, the spurned beau replied a few minutes later, calling her some not-so-sweet names and suggesting that she "share THIS e-mail with your friends."

"I was speechless," says Comer, who chose to not respond. "But eventually I was able to laugh at it."

When errant e-mails are sent at work, however, there's often much more at stake than personal embarrassment.

Three years ago, Jamie Diamond, 33, e-mailed his then-boss to ask about a client at the public relations firm where he was working. His boss wrote back, criticizing the client as incompetent and urging Diamond to "go around him if you want to get anything done."

Unfortunately, Diamond says, she also sent the e-mail to the client -- oops, make that ex-client.

"One click, and suddenly we'd lost a $5 million account," says Diamond, who is now self-employed as a publicist in Williams, Oregon.

Can you turn back time?

Short of erasing someone's memory, there is no surefire way to retrieve a missent e-mail. Microsoft Outlook has a "recall" function that can erase unread e-mails from the in-box of the recipient -- as long as the recipient is using the same mail client or server as the sender -- as does AOL, but only for messages between AOL users. (Both AOL and CNN are divisions of Time Warner.)

Then there's, an e-mail service which lets you tinker with (or even erase) messages that have already been sent by having the sender write e-mails that are created, stored and viewed on a remote server, where they can be edited or revoked at any time; recipients are actually accessing the e-mail on the remote server when they read the message, even though it looks like a regular e-mail.

But old-fashioned vigilance is probably the best way to avert these snafus in the first place. Roger Matus, CEO of e-mail archiving company InBoxer Inc. and keeper of the blog Death By Email, believes the easiest way to avoid these mistakes is to forget that the "reply all" button even exists. "Simply put, there is rarely a real reason to use it," he says. "Often, when you hit it, you end up e-mailing people who were blind carbon copied without realizing."

Matus offers the following tips on avoiding e-mail embarrassment:

• Type out the person's full name when addressing your e-mail. If you type just the first few letters and let your e-mail program fill out the rest based on your address book, it could easily misroute your message without your realizing it.

• Double-check the addresses of your intended recipients before you hit "send." Do you really want all the people to get this particular message?

• Be sure to notify your company's legal department if there is any chance that governance, compliance or privacy regulations were violated as a result of something you sent by mistake.

• Immediately notify the person who received the e-mail that it was a mistake and, if possible, ask them not to read the message -- or at least to delete it right away.

LifeWire provides original and syndicated content to Web publishers. Anna Jane Grossman is a freelance writer in New York City.

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