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New in Labs: Stop sending mail you later regret (gmailblog.blogspot.com)
51 points by robg on Oct 7, 2008 | hide | past | favorite | 55 comments



I'd prefer an option where I send it and it rests on gmail's server for X amount of time I specify (minutes, hours, days).

I could then go back to it and edit it at will or delete it before the send time has passed.


I saw the headline and had the exact same thought. "Oh, look, someone's invented that time-delay feature that I've wanted for years!"


That would have another use, too: hiding your sleep schedule from the recipient. You could write an email at 3:00 AM, set an 8 hour delay, and appear to have regular sleep patterns.


Or vice versa. From "The Dilbert Principle":

If you wake up in the middle of the night to heed nature’s call, take a moment to leave a voicemail message for your boss. Your message will automatically leave a recorded time-stamp, thus reinforcing the illusion that you work around the clock. This is a big improvement over reality -- that you chugged a beer before going to bed.


This is easy enough to do on a UNIX machine. Compose your message, then delay the sending with at:

    $ at 8:00am sh -c 'mail person@normal-sleep-schedule.com < my_message.txt'


Unless you want to delay it until birthdays or some other event that's weeks or months away.


at lets you specify dates as day/month/year. All you have to do is make sure the computer is running at that time, which is easy if you do this on your mail server.


That I know. I would never depend on a command line command to execute something months from now. Not on any system.


I want this so bad. I've looked before, but I can't find this feature anywhere.

But rather than setting delays I'd like to just define a range (say 8am–6pm) during which mail is sent. Anything outside that range would be queued until the next period.


Not that I use it, but I'm sure Outlook or any other POP mail suite offers scheduling.


BTW, I thought about similar feature - setting a desired reply date/time on e-mails you send, so the recipients MUA can automatically schedule it in users calendar (and/or remind him of replying you).

As of many people replying they need a feature no one has - here's opportunity of creating a completely new web e-mail system :-).


Something like this? http://www.addins4outlook.com/sendguard/

I've never tried it, though.


As always, the same two questions.

1) How to build it? (server-based or client-based) and 2) Who's going to pay for it?

It sounds like one of those things that a small number of people talk passionately about but there's not actually any money in making their pain go away. Or maybe -- beats the heck out of me where the payback is.

Client-side this is less than a week on the Microsoft platform -- a month if you want to handle all email clients. Server-side? I think you'd have to pick just one mail host and stick to customizing it.

One of the issues would be turning it off -- you'd have to have some kind of neato keypad test thingy to prevent drunken farts from just clicking the button and sending anyway. That leads me to believe a better design might be client-side.


It could be implemented as a variation on "saved drafts".

Since Gmail has a bunch of google lab apps in the gmail settings, it might well happen....

http://mail.google.com/mail/#settings/labs


How about sending your message to a kind of delaying-mail-proxy server could help?


Please pardon my garbled post. It's been too late.


That's a nice one. Didn't think about that. It's a nice compromise between client and server solutions.

Store-and-forward has another big set of issues though. File sizes and bandwidth requirements are easily non-trivial. In addition, there could be legal issues with keeping the data around for awhile and then forwarding that wouldn't exist if you just piggy-backed on some other app. In a way, it kind of puts you in the league with GMail and the other guys, right?


Totally agree.

Maybe it could be a greasemonkey-added "Send later..." button that you have to manually click on every time (to avoid thinking you sent an email, but it was actually put into a queue) along with an input box for delay-time.

When you click it, it could (1) add a unique identifier to the subject, (2) save the email in drafts, and (3) send a message to a server-side app (which knows your Gmail authentication info) with the ID of the message and the time it should be sent. Then at the appropriate time this app logs in, finds message by unique ID, gets rid of said ID, and sends the message.


I agree to an extent, but the problem is defining X before you send the email.

Let me put it this way: During the normal weekday, a 15 minute delay is probably sufficient. But coming home late on a Friday night, is 15 hours enough? Or, in some cases, 15 days?

So that's the question: how to define X ahead of time without knowing all conditions for which X applies? I suppose you could have date/time conditionals, but there would be instances where you probably violate your own rules.


Heh, let it depend on how many maths questions you get right.


I agree. However this might not be as effective as one would expect if you usually realize your mistake only once you're past the point of no-return.

In other words, if you know your mail won't be sent right away, will that delay the background, subconscious mental process of analysing your actions to see if you screwed up?


I was going to say the same thing. I probably edit at least 50 percent of my comments here and on reddit within a minute, and delete about 25 percent. Presumably a pause in mail sending would have a similar effect.


Maybe we'll see this ... obviously we all thought of this feature before and would enjoy this. Maybe they are listening?

Also, if they are listening I would like to be able to Twitter within Gmail. Have an inbox tab and a Twitter tab; spend all my time in Gmail & refresh Twitter a few times a day, why not consolidate?


exactly the approach i would have taken and i think their solution demonstrates, to some degree, what can happen when a company is focused on hiring engineers instead of great product people.


Let's not argue too much. I agree that what you say is true, but I wouldn't say it's a bad thing. Think back 30 years. Product people were thinking up new main frames, researchers were thinking up the Eldorado workstation, and hackers were thinking up personal computers.

Our industry has really benefited from a "throw it against the wall and see what sticks" mentality. Is this a good feature? I don't know, but I do like the idea of Google inventing 100 or 1,000 such features and seeing if one of them is a winner.

I am not so sure that a product management team with a gating and evaluation process will do a better job of picking features than--no offense googlers--a million monkeys randomly inventing features they think are neat-o.


Totally agree. And I'm sure I read Paul Buchheit somewhere saying that just this feature would make a good addition to Gmail.

What they did instead is so gimmicky it makes me cringe.


I've been asking for this for years to no avail. Even a ten-second delay would be enough to prevent a lot of "sender's remorse".


Too bad that I'm still good at math when I am drunk. I was out at a bar one night, and I "came to" walking down the railroad tracks on the way back home (way out of the way, and not exactly safe). I didn't even remember cashing out my bar tab, but lo and behold, when I checked my credit card transactions a couple days later, I tipped right around 25% ($85 total on a $67 tab) -- this is the same way I would tip sober.

If you want a moral in this story, don't drink two 1-liter mugs of micro-brewery beer within a couple hours and then continue drinking Guinness and shots ($30+ worth!) after relocating to a popular Irish bar.


funny they dont mention alcohol or drunkenness explicitly anywhere in the email, yet everyone knows what this is about.


I also liked their rationale for Chrome's "incognito mode": "For times when you want to browse in stealth mode, for example, to plan surprises like gifts or birthdays, Google Chrome offers the incognito browsing mode."

Google enables our vices without actually identifying them. :)


I actually did use Chrome's incognito mode to buy a birthday gift the other day. On the other hand, the gift was a vibrator. Not sure which side this ends up supporting.

(Regular YCer here, just don't need this linked to my actual name)


don't need this linked to my actual name

Yeah, you wouldn't want anyone to know you enjoy sex.


Actually, I wouldn't want the recipient to search for my name and ruin the surprise.


Either you're buying a gift for pg or you're really paranoid. Maybe both?


No: his or her bf or gf is a hacker too.


>alcohol or drunkenness

From experience one has followed the other. but YMMV ;)

I think both an email client and SCM client should be integrated with a breath tester.


Brilliant. Except for those individuals who prove more mathematically adept than socially to begin with...


It should have a difficulty setting, the higher levels could ask you to solve integrals or differential equations. :)


I'm still waiting for the downright trivial "bottom-posting" Labs application - it can't take more than a couple lines of code to have GMail set the caret below the quoted text, and have those couple of empty lines that Gmail generates appear after the text as well.


WTF? Looks like GMail is feature complete and they dunno what to do... I bet the next thing we'll see is random signatures. Looks like the are implementing a bunch of useless features that all got mentioned in Usenet 15 years ago.


Gmail Labs includes a ton of pet projects that various employees thought might be neat. Hence why they're Labs products.

I kind of like it when they implement stuff like that, just because it's fun.


I bet the next thing we'll see is random signatures.

If you try to actually turn this on in your Gmail settings, you will scroll past their random signature option.


i thought that this was an April fool's joke


There was a similar one. I think it involved time travel instead of answering math problems, though.


Surely google can correlate the contents of your mail with blogs on getting fired/splitting up with your partner/falling out with your relatives and advise you whether or not you should send it.


Funny you mention that, I used to have a Mac mail app (forget which) that had a feature like this. It did some kind of keyword counting thing and would display one, two, or three chili peppers next to inbound and outbound emails.

There was some scripting built in, and one of the things you could do was add a one hour sending delay to anything with a certain number of chilis.

The combination of visual display and scripted "let me sleep on it" features worked really well.


The chili-peppers language-analysis is Eudora's "Mood Watch" feature. Never used it, but always thought it was a good idea.

Similarly, email clients should catch references to attachments that aren't there, and ask "do you really want to send this without an attachment?"

Even more generally, they could recognize (and allow to be configured) certain addresses as requiring additional confirmation before sending -- so a mistaken overbroad or misdirected CC becomes less common.

(I'm thinking: first time you send to an address, you get a confirmation popup, and a chance to classify this address: require dialog confirm; require captcha/retype-of-name confirm; require waiting period; require confirm if combined with other address; etc.)


Similarly, email clients should catch references to attachments that aren't there, and ask "do you really want to send this without an attachment?"

This was a Better GMail (Firefox extension) feature that is now available in GMail Labs under Settings.


Thanks, it was Eudora!


Now we just need someone to write a greasemonkey script which auto fills the answers for you so you can send emails right when you want...


That was my thought as well.

Of course, the next step is to have an hardened mail goggles feature which requires you to write a greasemonkey script in order to send an email.


Beautiful. Now they just need one for texts, since that's where I usually get myself into late night trouble...


another version: Set timer on email, then receive a text message and you can reply (1) to send (9) to not send.


They need to make the questions harder!


What? Really? You people are crazy.




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