Google Inbox has this feature. There, after sending an email, a small notification appears, allowing you to 'undo' the send for a few seconds. For the small number of times you are too trigger-happy with the Send button, the ability to undo is great.

Yup. This feature had been enabled for me for years without use. Then last week I needed it and it made it all worth it.

Gmail has this feature, too. It basically holds the message for up to a minute after you press send. During that time you can click the undo button and edit the message. After the time, the message is sent and you can't undo it.

In reality, I think the only way to do this is just not to let the email leave the bounds of their own servers for x seconds, and then only if the user hasn't canceled in the meantime. Maybe it's possible to do if you host the email for both sender and receiver, but even then, it seems unlikely given the implications of being able to see an email literally disappear from your inbox.

Exchange offers this functionality - retract an email sent to internal senders. It sometimes fails with "The sender would like to retract this message" shown above the email.

I have only seen this fail. Literally never seen it succeed but we are on O365 so maybe it used to work?

Hilarious though to see people try.

I once worked with a guy who had an Outlook rule that immediately marked new mail as read ( and flagged 'to action' or something like that ) specifically to defeat Exchange recall.

Admittedly he did manage to harvest some interesting information but mainly it was just managers trying to correct typos.

It was effective before blackberries (and the iphones that killed them). Basically it worked when there was a chance that you'd hit recall before anyone's mail client would have actually pulled it down.

I saw people (try to) use it a decade ago. Same result.

Well, if it succeeded, you wouldn't see it.

Along those lines, the Outlook developers forgot to implement message recalls on the Mac client.

Maybe it's the Unix fan in me talking, but I don't get the point of "undo send". Why are you hitting "send" if you have doubts about sending, instead of putting it into the Drafts folder and taking a 10 minute break? If you're afraid of sending an email with a typo, why not get into the habit of proofreading to your satisfaction before sending the email?

"Undo send" seems to me to be inherently inferior to having some self-discipline and patience. Whatever last second doubts you've had are now simply pushed forward. Except now you've set a timer, which creates additional chance for failure -- either on the back end or on the user side, e.g. the timer expiring just as you try to panic cancel -- that there isn't when you just don't hit send in the first place.

I get that products have to be designed for human comfort over pure technical effectiveness, but this is design that appeases -- at a very surface level -- one of our least helpful indiscretions.

> Undo send" seems to me to be inherently inferior to having some self-discipline and patience

I eagerly await your new email client which provides both self discipline and patience to users. Until it releases, I suspect the Undo Send option will continue to be used.

But email has been this way for a very long time. And aren't many other common user-to-user messaging systems this way? iOS messages and old-fashioned texting/SMS, for instance. And postal mail and phone calls and answering machines and face-to-face interactions, for that matter.

I think of it as more important when email is being used as an announcement medium - I'm ok leaving a mistake/sending a correction to one or two people, but not 1100.

Presumably you also put more time and focus into emails that are being sent to 1,100 recipients versus emails to 1 recipient, and you send more of the latter than you do the former. But the "undo send" gives you 10 minutes of extra-edit time to that important announcement as well as every other email you send.

If "undo send" gives a psych boost to being obsessive-compulsive, this still doesn't address the additional layer of possible failure. You have better control over your ability to not hit "Send" then you do to do a panic cancel as you do a last second proofread.

I accidentally ctrl+enter fairly often when formatting emails.

You're trying to cram everyone's problem into the same box, it's silly.

There's plenty of reasons you might undo an email if you had the chance.

Taking a 10-minute break is not something I've ever done before I sent an email.

I've done that too. For emails and for things that have an undo/delete option since their inception (Twitter, Facebook, Slack). With email I've accepted to be more careful about when sending very important emails. And for less important emails, be OK with sending an addendum, even when it's on a mailing list.

I've unintentionally sent emails by absent-mindedly hitting the wrong sequence of keys on my keyboard.

Your method requires putting extra time and effort into every email you write. "Undo send" requires extra time and effort only when something goes wrong. Email isn't for instant communication, so adding a short delay to make it easier is a good tradeoff.

Its for when you accidentally click send, not for emails you regret.

It's definitely for both. Like that scenario where you copy edit something for hours and as soon as it's sent you see a typo for the first time.

I'm sure there's a law that no matter how carefully you proofread something, you'll find at least one typo the first time you read it after it's been published.

As a human, I like to have tools to fix/prevent human error.

Yeah seriously.

I don't understand why people keep making mistakes.