As OS X updates over time, some functions don’t work the same anymore. Some commenters have provided solutions in the comment section. Make sure you check them out if things don’t happen the way as described in the post.
Found an easier way to schedule mail on Mac to send it later at a specific time I want by using Automator iCal Alarm.

When you open Automator, it immediately asks you to choose what you’re trying to build:

Building an iCal Alarm will automatically set a new event in iCal with the alarm action set to be whatever you design in the Automator.

So I want to send an email at maybe 9am tomorrow morning, I can open Automator and build an iCal Alarm like this:

  1. Get Specified Finder Items
  2. New Mail Message (type your mail here - leave recipient blank if you’re sending group mail and add the two extra steps below)
  3. Send Outgoing Messages
  4. Save

You may skip step 1 if there’s NO attachment. You can also send group mail (with/without individual salutation) at a later time by adding these steps between steps 2 & 3 above:

  1. Find Address Book Items (find Groups)
  2. Group Mailer (check “add greetings” for individual salutation)

Then in iCal, you’ll see a new event set at the time you hit “save”:

Then edit the date and time of the event and the alarm time to whenever you need it.

DONE!

    However, from experience, attachment doesn’t work for Group Mailer. So, if you wish to send a mail with attachment to a big bunch of people, stick to the 4-step solution. The only drawback is it can’t take group name as recipient, i.e., all email addresses are disclosed. If you wish to keep mailing list confidential, you’ll need to add your group to Bcc list.

    You may also set the alarm to be repeated periodically and have the same mail sent to the same recipient(s), say, every month. This would be really handy to someone who needs to send out reminders periodically.

    I’m still working on getting Apple Mail to send all drafts at once so that I can incorporate Serial Mail and Apple Mail and Automator. The problem is Apple Mail seems to be incapable of sending more than one mail at the same time. It can send 100+ emails consecutively very quickly (like really immediately one after an other) but just not when you “select all” in drafts box then hit “send” in file menu (or shift+command+D).

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