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Sending email at the right time can mean the difference between receiving a prompt response and waiting all day. As someone who lives in Australia with colleagues who mostly reside in the US or Europe, I know what this feels like.

Apple’s Mail app doesn’t come with a scheduler by default, but that doesn’t mean you can’t prepare messages in advance and send them at a later point in time.

Why Delay?

Aside from the aforementioned nature of working in a world that never sleeps (even when it’s dark), scheduling email has a few other benefits too. The first is about managing expectations – how is anyone ever going to know the best time to reach you if you’re always available?

We exist in a world dominated by read receipts, where we feel compelled to reply to anything the second we have seen it – even if it’s 3 a.m. Maybe you work best at unholy hours in your pyjamas, but your coworkers don’t need to know this when you can schedule everything for 8 a.m. on Monday morning.

Finally there are a few other compelling reasons to delay sending that email. Maybe it’s really important, and you need to read over it before you send it. Maybe it’s someone’s birthday next week. Maybe the recipient is away for 2 weeks, and you’d rather yours be near the top of the pile when they return.

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There are two ways of doing this on your Mac. You can either make do with the software you already have, or invest in a cheap paid tool to make life easier.

Scheduling With Automator

Automator is probably your Mac’s most neglected program 3 Easy-To-Create Simple Automator Workflows For Everyday Use 3 Easy-To-Create Simple Automator Workflows For Everyday Use Read More – find it in the Utilities folder, or search for it using Spotlight. It allows you to record workflows and automate all kinds of tasks, saving time and effort. You can use Automator to schedule an email by creating an application that sends your message, then scheduling that application to run.

1) Open Automator on your Mac and choose Application when prompted.

2) Under the Actions sidebar choose Mail, then click and drag New Mail Message into the panel on the right.

3) Enter the recipient and contents of your email. If you would like to send multiple emails at this time, keep adding them using the New Mail Message action.

4) Finally click and drag Send Outgoing Mail into the workflow, ensuring it’s at the very bottom.

5) Hit File > Save and make sure “Application” is chosen before saving.

6) Open Calendar, navigate to the date you would like to send your message and create a new event.

7) Double-click the event to bring up its info, click on the date, then activate the Alert drop-down menu and choose Custom. In the box that turns up choose Open file, and point it at the Automator application you just made. Adjust the timing if you like, then click OK.

And that’s how you schedule mail using Automator and Calendar, provided your Mac is awake at the time you have set it to schedule. You can get much more fancy with this (like adding attachments and setting up regular alarms) and there are even Calendar events within Automator to play with, for even deeper integration.

Of course, it is a little bit clunky…

Or Use SendLater Instead

If you think you’re going to be scheduling a lot of email, SendLater from Chungwa Soft might be worth the relatively low €8.95 price of entry. It’s a very simple tweak that adds an additional “send” button to Mail.app, using which you can schedule a message to send at a later date. Until you choose to buy it, it will nag – but there doesn’t appear to be any more restrictions.

The benefits of using this app outweigh the cost if you have a specific need for scheduled email. The ability to compose messages within your regular app, schedule replies, use auto-completion for adding addresses and anything else Mail does is still there, without the clunkiness of having to resort to Automator.

SendLater strives for user-friendliness, and that’s what you get. For the occasional single email, Automator is more than capable. For more regular scheduling purposes, use SendLater. Note that it too depends on your Mac being awake!

There’s also an add-on called Send Later for Postbox/Thunderbird, so check that out if you’re tempted to switch mail clients The Search for the Perfect Mac Desktop Gmail Client The Search for the Perfect Mac Desktop Gmail Client Need a desktop client for Gmail on your Mac? We put ten to the test. Read More . If neither of these methods are suitable, or you spend a lot of time inside the Gmail web interface, you might have more joy with Boomerang for Gmail Schedule Emails to Send Later with Boomerang for Gmail in Chrome Schedule Emails to Send Later with Boomerang for Gmail in Chrome Gmail is in ingenious tool for managing emails. Much of what it is lacking per default, is covered by Gmail Labs apps or browser add-ons. Boomerang is a browser add-on available for Chrome that let's... Read More instead. You can even build an all-in-one point of access for your other accounts using Gmail, and kiss goodbye to mail clients for good.

How do you schedule your email?

Image Credit: Hope for Gorilla (charleyBook)

  1. Danny
    December 8, 2016 at 5:02 am

    Please edit this article to say that you must create a "On My Mac" calendar. This option will be hidden if you don't already have a local calendar! To do this (with Yosemite) you must disable all current online calendars in the account preferences. Now, when you select File->New Calendars-> "On My Mac" will appear. This took about 2 hrs to figure out...

  2. ah
    April 3, 2016 at 6:58 am

    too bad Send Later is now ridiculously expensive I had it when it was just a simple app and now bundled with Mail Butler for personal use it's way out of price range

    • Tim Brookes
      April 4, 2016 at 2:04 am

      Wow that sucks, I didn't realise it had been swallowed up. You might have joy using one of the other solutions (scheduling mail with Calendar) which won't cost you, or you could go all-out and pay a once-off fee for a client like AirMail which already supports the feature.

      After having a look it seems like MailButler is free for light users, but you only get "30 actions" per month on this model. Their definition of an action is basically using any of the included features, so you might get on ok if you don't need to make heavy use of the feature?

      The monthly charge for the service sucks though. I could understand a one-off payment, but €8 per month (or slightly "cheaper" at $70ish per year) seems ridiculous. Maybe Apple will introduce the feature with OS X 10.12, they've put a lot of work into Mail in recent updates!

  3. Ian
    March 31, 2016 at 5:32 pm

    If the computer is off at that time, but is turned on later, will the email send as soon as the computer is turned on? Also is there a good free animator app for android phones? That would solve the problem of my laptop being off at the time I want the email to send.

  4. ele
    March 11, 2016 at 10:26 am

    Hi, but if i want to schedule the answer of an email?

  5. Hemant kumar arya
    February 11, 2016 at 4:18 am

    Awesome post, Now we can schedule mail in Gmail by juat downloading a extension named as boomerang in you chrome or firefox. Thats all you can schedule email free of cost. Thank you :-)

  6. TT
    January 10, 2016 at 1:38 pm

    For those of you who are having the problem of the alert disappearing - the problem is that your calendar is connected to icloud. You need to create a calendar on your mac, this will make the 'open file' alert work. Here is a text that helped me solve it:

    "OK guys- here's the problem. If you have iCloud Calendar turned on it means you want whatever file to open when you trigger it with an alert to happen on all your iCloud devices. It can't do that, so it won't (can't) hold the alert. You have to go to System Preferences>iCloud and uncheck Calendars. Then create a local calendar and try your alert again."

    and

    "I was too hasty in my previous reply- let me clarify.

    You can still leave "Calendars" checked in iCloud System Preferences- in fact if you share a calendar with any other device this needs to be checked. But if you want to use alerts to trigger opening a file or application (like an Automator app) on your laptop it has to be on a non-iCloud calendar. You have to create a local calendar "On My Mac" called "My scripted events," or something like that.

    For example, I want to set a date and time to open an Automator app I created called "Launch Slideshow." If I try to add an alert to open that file on an iCloud calendar, iCloud wants to open the file "Launch Slideshow" on my phone, my iPad, and everything that accesses that calendar in the cloud. This is impossible, even if I in fact have the file "Launch Slideshow" on the other devices because the path name is ultimately different. So calendar can''t hold the alert. Scripted events in Calendar have to be on a non-cloud calendar.

    Clear as mud?"

  7. idim
    December 6, 2015 at 11:04 pm

    When i hit apply the alert, the alert details disappear!! Hundred times the same result!!

  8. reefcomber
    September 19, 2015 at 1:11 pm

    I created an Automator application to send attachments automatically.

    The workflow is as follows: Get Specified Finder Items, New Mail Message, Add Attachments to Front Message, Send Outgoing Messages.

    I then created an Event in Calendar that launched the above application. Everything worked fine, except that the message was not sent. It automatically created the message, sending to the correct email address on the correct date, but the message did not automatically go out.

    Am I missing a command in the workflow?

    Thanks

  9. Byron Bray
    September 13, 2015 at 5:09 pm

    I'd like to point out a couple of tweaks, in the use of Automator to schedule emails, that may make it a little easier and more predictable to set up and test:

    1) If, in testing this method, you set up a Calendar event to run an Automator application, you may find that it does not work, at first. This may be due to the fact that the event is still open in Calendar and may not have been saved. When you create Calendar event, the program doesn't necessarily save the new event until you move to another event or another day. You can ensure that your activating event is recorded by clicking 'Apply' or by clicking on another day or event, so that the newly-created event is actually added to the Calendar data file.

    2) Since you've created a new application, the File Quarantine alert may be activated the first time you try to execute the new application you've created. If you're not there to approve it, the app may not execute. You can prevent this problem by inserting your own email address and some dummy-text in the message, when you create the Automator application, and then executing the application manually, so as to invoke and approve the File Quarantine alert before you actually employ it.

    • Trish
      November 28, 2015 at 1:40 am

      I've clicked 'Apply' but the Alert details immediately disappear. What am I doing wrong?

    • Ross Heitkamp
      March 24, 2016 at 5:51 pm

      I am still having trouble with #2 - the file quarantine. I tried setting it up with my own email address and see that the second time this is scheduled, I don't get the warning. BUT, when I save the automator again for any reason, File Quarantine appears to reset and want to confirm execution again. So there appears to be no way to change the addressee without ending up blocked by File Quarantine. I'd have to send them one message just to get past quarantine. Apple has become quite an obstacle with its nanny software.

      • Ross Heitkamp
        March 24, 2016 at 7:00 pm

        I figured out a workaround to the File Quarantine obstacle with changing the addressee. If you send the message to an addressbook group, then you can test and approve the execution of the script while having your own email in the group, then change the group recipient to your intended one before your scheduled sending time.

  10. Nicko
    May 18, 2015 at 3:43 am

    Calendar doesn't seem to play nice for me when adding in a custom multi-day-per-week repeat with the open file procedure when scheduling.

  11. Doni1985
    May 1, 2015 at 11:02 am

    THANK YOU so much! Terrific - I love Automator <3

  12. Tim Brookes
    April 27, 2015 at 12:34 am

    Yes that's true, though once you've opened the application once and given it permission to run you shouldn't have that problem again.

  13. Wayne Smith
    April 23, 2015 at 1:53 pm

    Good article and very well detailed. One problem I'm having is the "Your opening the application "x" for the first time..." warning. This means that, if I'm not at my computer to click "open", when the iCal event opens the email will not send.

  14. Wayne Smith
    April 23, 2015 at 1:49 pm

    Good article and very detailed. One problem I'm running into is the "Your opening the application "x" for the first time" warning. This means, if I'm not at my computer when the iCal event takes place, the email will not send until I tell OS X to open the application.

  15. Kaloyan
    April 6, 2015 at 8:46 am

    Great article.

    Do you have any recommendations for an OS X app that schedules incoming emails? Instead of receiving each email as it comes, I'd like to get emails at specific time slots.

    • Tim Brookes
      April 14, 2015 at 12:53 am

      Hi Kaloyan,

      This functionality already exists in the default Mac email client. In order to receive email periodically, launch Mail on your Mac, click Mail at the top of the screen, then click Preferences. Under the General tab change the Check for new messages field to an interval that suits you.

      You can't designate specific times, but if you want email every hour or every half-hour (or a custom period, say 90 minutes) then this allows you to do that.

      Hopefully this helps you out,
      Tim

  16. Kyle
    March 19, 2015 at 12:36 am

    I am having trouble saving the event. It sets it up but when I leave the event window it deletes the open file reminder. Anyone have a idea as to why?

    Thanks
    Kyle

    • Trish
      November 28, 2015 at 1:38 am

      I'm the same. Did you get an answer to this?

  17. inge
    February 22, 2015 at 11:38 pm

    what if I want all my emails to go into an outbox, before actually sending them, like in windows live mail.. and then when I`ve reread them and I want to send them I want a send/receive option (like windows) so that all emails in my outbox get sent at once

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