Have you ever clicked “Send” on an email and regretted it a fraction of a second later? Whether you were angry and typed something you shouldn’t have, clicked “Reply All” when you wanted “Reply” or just accidentally clicked the “Send” button before the email was finished, your first instinct is to find and click an “Oops!” button. Unfortunately, there is no such button for email … or is there?
While I can’t tell you how to unsend email you might have sent already, I can give you four ways to set up your email so you can undo them in the future. Taking a few minutes now can save you a lot of embarrassment later.
Gmail ‘Undo Send’
Google’s Gmail is an incredibly popular email system, thanks to its powerful and customizable inbox. It also has more features on the back end than you can shake a stick at, and it’s adding more all the time.
One feature Gmail has had for years is “Undo Send,” but it was experimental and buried away. Now it’s front and center, and you just need to enable it.
In your Gmail account, click the gear icon in the upper-right corner and choose “Settings.” On the “General” tab, scroll down and find “Undo Send.” Click the checkbox for “Enable Undo Send” and choose a cancellation period of 5, 10, 20 or 30 seconds. (This is how long you have to call it back before it gets delivered.) Once you have that set, scroll down to the bottom of the screen and click the “Save Changes” button.
Now when you click the “Send” button on a message, you’ll see a message appear at the top of your inbox with an “Undo” link. As long as the message is on the screen, you can click the “Undo” link and the email will reappear, ready for editing or deleting.
Of course, maybe you want a grace period longer than 30 seconds or you use a different email service. I’ve got something for you, too.
Browser plug-ins
There are a few browser plug-ins that offer unsending features. The first one we’re going to look at is Criptext. Right now, it’s just for Chrome and Safari, but Firefox and Outlook program versions are in development.
When you enable Criptext on an email, it encrypts the message and any attachments, tracks it so you know when it’s been opened and gives you the option to “recall” it. You can also set messages to expire after a certain amount of time.
UnSend.it is a service that works with more browsers and email services than Criptext. It does everything Criptext does, except encryption. You will also need to configure your email service to run through UnSend.it’s servers.
Once that’s done, you can send email and attachments to anyone. If you decide to unsend the email, just click a button in your email service and they won’t see it anymore. You can also track when someone opens the message or set it to self-destruct after an amount of time.
Both of these services work by turning the text of your message into an image, then sending that image on to your recipient. Because the message is served from their servers, they can delete the image and it will disappear from your recipient’s inbox.
The email will still be there, but it will be blank. Unless your recipient took a screenshot, he won’t have the information.
But if you really want to take things to another level, keep reading.
Secure messaging
Most free messaging systems aren’t really that secure, which is why a former NSA employee decided to take matters into his own hands. The result is called Virtru.
Virtru is a plug-in for Firefox and Chrome that works with Gmail, Yahoo and Outlook.com. There’s also a plug-in for Outlook 2010 and 2013, along with apps for Apple and Android.
The free version of Virtru lets you send secure messages to anyone. If the other person has Virtru, she can open the message in her regular email. Otherwise, she’ll need to get Virtru’s free Web viewer.
If you upgrade to Virtru Pro for $2 a month, it adds message revoking and expiring, along with the ability to see and control message forwarding. Learn more about Virtru’s features and step-by-step instructions on how to use it.
Email isn’t the only place you can unsend things you regret. Find out how you can take back embarrassing posts on Facebook.
