The Wonder of Undo Send

The finality of a sent email can be terrifying. As soon as you hear the “whoosh” on your smartphone or see the words, “Your message has been sent,” a palpable anxiety sets in. Mistakes were made. Possible misinterpretations. Poorly communicated emotions. There was a misplaced modifier. You accidentally hit "reply all." You used a first initial when a full name would have been more appropriate. The subject line wasn't funny and referential enough; the sign off wasn't earnest enough. Maybe you should have used a period

As a chronic worrier, I use Gmail's “undo” button incessantly. I un-send almost every email at least once, maybe twice depending on the recipient. It is no exaggeration to say that it has saved my social and work life multiple times. I don't send emails anymore. I unsend them.

The idea of “undo” was born in the mind of Google designer Michael Leggett and engineered by Yuzo Fujishima. Leggett had been working at Google Finance in 2006 when he accidentally sent an unfinished email to a Google executive. Aiming for the “Save Now” button, he missed and accidentally hit “Send.”

In 2007, Leggett moved over to Gmail. He had been pitching the rough idea of “Undo Send” when he heard that Fujishima was working on a similar concept. Fujishima wanted to create a special outbox where an email could sit in limbo for five minutes before sending so that a user could edit the message. Leggett worried about the complexity of this extra outbox and reached out to him for collaboration. Together they strove for something cleaner and simpler.

In March 2009, the feature made its debut in Gmail Labs, the tool box that allows users to opt-in to certain experimental features that “aren’t yet ready for primetime.” Click the gear icon in the right-hand corner of your inbox, drop down to “Settings,” and among the labels you’ll see at the top of the next page, sits “Labs.” Scroll down and you will have the option to enable “Undo Send.” Which you should if you haven’t already. I promise it’s worth it. And if you don't like it, you can always undo it.

As a concept, undo has its roots in a 1976 IBM report that noted that "It would be quite useful to permit users to 'take back' at least the immediately preceding command (by issuing some special 'undo' command)." It would be up to the wizards at Xerox PARC to assign to it the Control-Z keystroke, ushering it into nearly every piece of software.

Though the option to undo an action might seem a little out of place for an email setting, the idea has been broached before. Those of us who used AOL back in the day might recall a similar feature. But there were two major drawbacks to AOL’s version. First, it only applied to in-network email addresses. Second, it was worthless if the recipient already opened the email.

The latter concern isn’t a problem with Gmail. In fact, the name of the feature is an intentional misnomer, as no sending actually occurs while the “Undo” link hovers over your inbox. What actually happens is that the message is sent to the server, but just before sending is complete, the process stalls for a few moments, somewhere in that cloud. Hitting “undo” during that time jerks the email back into your browser in the form of a draft, which you can proceed to alter as needed.

A more honest description then might be “Delay Send.” But as Leggett points out, this would be confusing. “I didn’t want users sitting around waiting for an email to send for real,” he wrote in an email to me (which he admitted to un-sending once). “You had to have the confidence that it was in fact sent, that you didn’t need to wait around for it, and you want the right trigger word when you want it back. There was never another option in my mind.”

The functionality of the idea seems obvious now, but surprisingly, Google needed some convincing. According to Leggett, the initial reaction was, “That’s awesome!” followed swiftly by, “But it is really hard because it touches a lot of pieces of core infrastructure and we’re busy right now rewriting the front end. Maybe later.”

It remains a complex feature, which is why it still sits in Gmail Labs after all these years. But Leggett says that Google knows that its fans are legion (if quiet) and hints that the option will eventually escape the barriers of “opt-in and graduate to all users.

A 2011 study on regret on social media found that, well, regrets on social media are incredibly common. They occur for a variety of reasons (venting frustrations, lack of foresight, spontaneity) and usually became regrettable only later, after unintended consequences arose.

In light of their results, the researchers recommended an "undo" option for social networks. They suggested building a tool that could somehow preemptively identify regrettable posts. “That tool might intervene with reminders or warnings,” they wrote. “Or it might delay the posting for a few minutes to give the user the opportunity to reconsider,” just like “undo.” (Another Google Labs feature called "Mail Goggles" requires you to solve a math problem before you can send an email, which is a pretty good way to prevent drunken emails, unless you're a math professor.)

“Undo” fits beautifully into email because textual communications are so fraught with uncertainty and misinterpretation, so potentially intimate, and so immediate. They're designed for near-instantaneous communication; they beg for immediate response.

I asked Leggett if he wished there were other situations that had that option, either on or offline. “Yes and no,” he said. “If everything had an ‘undo’ button, that would be awesome…ish. But we’d also then be even less in the present, obsessing about what we did a couple minutes ago and wondering if we should undo and redo it better.”

I thought about it and realized that I tend to agree. I love undo, but life is partially about taking leaps and fucking up and dealing with it. So as much as I wish I could “undo” a few conversations and text messages I’ve had this week, maybe the wiser and more mature path is to just send that metaphorical email, regret it if I must, and learn from my mistakes.

Or maybe not, sometimes.