Gloss How-To: ‘Unsend’ Emails and Avoid Embarrassing E-Gaffes

“OMG, I cannot believe I just sent that.”

At one point, everyone sends an email that they regret almost immediately. Maybe you noticed a misspelling in your cover letter or that you forgot to attach a résumé just a split second too late. Maybe you realized that you made a catty comment to the person it was directed at. Or, maybe you made a number of embarrassing revelations about your boyfriend’s bodily fluids or perhaps you accidentally sent some lewd emails to the other members of the Cornell University faculty.

Shakespeare may have written, “Let’s not burden our remembrance with a heaviness that’s gone” but he probably never sent the entire office a lengthy, detailed email account of his super steamy date the night before, after accidentally hitting “reply all.”

Thankfully for trigger-happy emailers, some cool (and little known) features are helping users better navigate their social and workplace inbox and preventing email misfires  - all with just a click of the mouse.

But until real-life takes a cue from live television and implements a 6-second delay, here are a few ways to save face, “unsend” errant emails and hopefully avoid any mortifying disasters.

How to “Unsend” Emails

Gmail

When Google launched the Gmail “unsend” feature last spring, users only got a five second window to unsend emails. But as of last week, you now have up to 30 seconds to undo any potential email gaffes.

1. To set up the “unsend” feature, open your Gmail page and click on the green beaker “Labs” icon located at the upper right hand corner (pictured below). If you don’t see the icon, click on “Settings” then the “Labs” tab. Scroll down to find “Undo Send”, click to enable and save your changes.

2. With the default setting, you’ll have a 10 seconds to undo a sent e-mail but if you go to “Settings” in the top right corner, then under the “General” tab, you’ll find “Undo Send” options that let you can change to a five, 20 or 30-second window. (Just make sure to save your changes!)

3. Now an “Undo” button will appear with the “Your message has been sent” confirmation whenever you send an email. Once an email is unsent, it will be saved as a draft to revise or edit, and a message will confirm that it has been undone.

But because this life-saving feature is part of Gmail Labs, it’s still being tested so it might not always work as intended… so your best bet is probably to exercise some caution when you email.

Microsoft Outlook

1. Go to the “Tools” menu, then “Rules and Alerts” and click “New Rule …” In the “Start from a blank rule” section, select “Check messages after sending.”

2. Click “Next>” two times or until you see the “Select Action(s)” page. Once you check the box “defer delivery by a number of minutes,” you can now click on the edit box with the underlined “a number of.” Here, you can specify a delay anywhere from one to 120 minutes long.

3.  If you’d like to select any exceptions to the ‘delivery delay’ rule, click “Next” and set your preferred settings. For example, you may want emails marked as ‘important’ to bypass the delay and go out immediately. Name your rule and select “Finish” to return to your Outlook page.

All emails will be delayed according to your settings and stored in a separate Outlook outbox, located in the mail folders under “All Mail Items,” during the delay period.

Hotmail, Yahoo! and AOL

While each email service offered a limited form of “unsend” at some point, the features are no longer available so once you hit “send”, it’s gone.

4 Tips for Avoiding Embarrassing, Potentially Disastrous E-Gaffes

1. Always check the “To:” field before you click “Send.” The auto-complete can be both a blessing and a curse!

2. Sleep on it. For emails written under extreme emotion, it may be best to put them aside and let yourself cool down before you consider sending anything.

3. Use drafts folders carefully. Even if it’s saved as a draft, an email in progress can still be sent by accident – regardless of the email service. For lengthy and/or important emails, use a separate Word document to compose your message and copy-and-paste into an email to send.

4. To Send is to Publish. Even “confidential” emails can be easily published online. Once viral, an embarrassing email can spread across the Internet at an exponential rate, and wreak havoc with reputations. When in doubt, follow the adage of “Never write anything you wouldn’t want to see on the front page of tomorrow morning’s New York Times.” (As a publicist, I could not stress this point to my former assistants and interns enough!) In short, think twice before writing something that could come back to haunt you. Comments and jokes via email are too easily misconstrued, even if they include a multitude of exclamation points and happy face emoticons. And you can’t wipe your hands clean just by deleting sent emails — all of your long forgotten and deleted messages are still floating around on the company’s server!

Bottom line: Google’s “unsend” feature is great but it can only do so much to save us from ourselves. Your best bet? To tread lightly and type very carefully!

Have you ever committed a major email faux pas? What’s your worst email disaster?