Can I schedule an email to be sent automatically at a specific time with Automator?

Look to iCal for your scheduling needs. You can have iCal run your Automator workflow. And Automator should already be on your system in Applications -> Automator.

If you do not like iCal for scheduling, there is always launchd .plists, or cron, or a few 3rd party utilities that can scheduled event execution.

Automator can compose a message and send it. But Automator does not have a scheduling service.

Applications -> Automator

New Mail Message

Fill in the details

save as an save as an application

Applications -> iCal

setup the recuring event

edit the event -> Alarm -> Open file -> Your saved Automator application

Try creating an action like this:

Enter your message and address information in the New Mail Message. Save the automator action and have iCal fire it off.

Should work

The best way to have scheduled emails sent is by using LetterMeLater.com.

I've been using this site for a year and works flawlessly. It allows me to select any time to send and I don't need to be connected to the internet in order for the email to be sent. I simply enter the content, subject, who I'm sending it to, the time I want it sent, and the site does the rest for you!

Check it out at LetterMeLater.com

Set up your Automator like this. I use this setup for repeating meetings and am doing so in OS 10.10.2 (Yosemite). Be aware when you set this up and save it will automatically compose and send the email immediately.

Open Automator, choose Calendar Alarm, Search "mail", drag "new mail message" to the right gray open area, drag "send outgoing messages" below this. Once you compose your message and add your recipients save your work. The calendar event will be added to the calendar at the time you saved your work. (You clicked save at 12:01, the event will be saved to the Calendar at 12:01. This will also automatically send out the email at that time, so just be aware of that. Once in your calendar, you may augment the times and repeats as you see fit, just like a regular event.