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Back in the day, I remember having an e-mail program (perhaps it was Eudora?) that could schedule the sending of mail, so when composing a message, you could set some preference for when it would be sent. The message would be composed and queued up, but would not send until the computer was connected to the internet at or after the schedule time.

Is there a way to duplicate this feature in Apple Mail? Specifically, I want to compose a message, but rather than clicking "Send", I click "Delayed send" (either from the Services menu, the AppleScript menu, or, ideally, from an icon magically added to the Mail toolbar, but I don't expect that will be easy to pull ofF). When I do this, I'd get a dialog box asking me when I want to send the message. I enter the information, and the message is queued up and will be sent at the soonest time after the scheduled send time/date when the computer is on and connected.

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Is a third-party app or service acceptable? –  timothymh Mar 24 '12 at 2:13
    
If I can invoke it from Mail and it is installed on my computer (i.e. not mailing a message to some custom address where their server sends it later), sure. –  Daniel Lawson Mar 24 '12 at 2:14
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Seems like most of us had the same idea. ;-) –  afragen Mar 24 '12 at 2:27
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@afragen True that... –  timothymh Mar 24 '12 at 2:32
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Try chungwasoft.com/sendlater (I'd love to give it as answer, but I only have StackOverflow reputation) –  mahal tertin Dec 2 '13 at 13:39
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4 Answers

up vote 10 down vote accepted

It is possible to achieve this effect using Calendar and Automator:

  1. Open Automator and create a Calendar Alarm.

  2. Use the tasks "New mail message" and "Send Outgoing Messages" and customize them as required. (Fig. 1)

  3. Save and move the event in Calendar to when you want the message to be sent. (Fig. 2)

Fig. 1:

Automator scripts

Fig. 2:

Calendar event

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Unfortunately, Andreas Amann's Mail Scripts is broken in OS X 10.7. I tried it and it did not work. I wish there was another simple solution that works on 10.7 and now 10.8. –  user27757 Aug 21 '12 at 5:50
    
@manuel does the iCal example that makes up the majority of this work for you. Others have up voted this, so it's likely to work. –  bmike Feb 10 '13 at 3:30
    
@bmike the iCal example didn't work for me, but because I skipped one step inside the step! I could easily set it up, but the email wasn't sent on scheduled time. It created the email, but didn't send it. Guess why... But no idea why even keep the mention to Andreas script here! –  Cawas Jun 6 '13 at 13:14
    
@Cawas If someone was on OS < 10.7, it could be useful. –  timothymh Jun 11 '13 at 20:35
    
@timothymh but it's already in the other answer! :) also, doesn't this work on OS < 10.7? –  Cawas Jun 11 '13 at 20:43
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No promises, because some of the scripts break under OS X 10.7 Lion, but you might find your answer by using Andreas Amann's Mail Scripts which includes

Schedule Delivery (Mail)

Allows you to send individual messages at predefined times (this script uses iCal for scheduling message delivery).

Andreas makes the source code of his compiled scripts available. You can download the .dmg

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I don't know if the specific script will still work, but try Mail Scripts from Andreas Amann. There is a Schedule Delivery script that used to create an iCal event that would trigger the message being sent. –  afragen Mar 24 '12 at 2:24
    
Mail Scripts plus energy saver scheduling a start/wake event might be a great combination to ensure the Mac gets up to send your most important message (assuming you might have several queued). –  bmike Apr 14 '12 at 20:44
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The simplest way I know is to save a draft and then set a reminder on iOS so I get bugged to hit send.

It's not ideal, but works in practice when the sending of a message at the exact moment is worth more to me than uninterrupted sleep (or whatever else might be going on in my life).

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Out of curiosity, do you think this is a better idea than setting an iCal alarm that automatically sends the message? If one is already depending on iCal, why not let iCal do all the work? –  Daniel Lawson Apr 14 '12 at 21:48
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Not at all - if you don't mind the formatting of iCal - that is a far superior answer. I just wanted to put an "outside the box" answer up. –  bmike Apr 15 '12 at 0:03
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There is a plugin for Mail app which name is SendLater:

enter image description here

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