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Automator will start with a project type selection window. If not, choose File > New from the top menu. Then select “Calendar Event” and click the “Choose” button. Click the Record button. The first time you record events with Automator, it will ask you to enable OS X Accessibility features. Follow the Automator’s instructions to open the Accessibility window and check the “Enable access for assistive devices” check box. Next, close the accessibility window and click the Record button on Automator.
A small window will appear, indicating that the Automator is recording your actions. Click on the iTunes Downloads window’s top bar to get it in focus. Next, click on the “Resume All” button. Click the stop button on the “Automator: Recording” window.
The Automator window will appear, showing you all of the recorded steps:

From the Automator top menu, go to File > Save and give the workflow a name. I usually use “Download iTunes”. This name will show up on the Calendar as an event. When you have finished saving the file, the Calendar app will launch. The event you just created is set for today’s date. Change the event date and time by double-clicking the event and clicking “edit” on the pop-up window. Set the desired date and time for the scheduled iTunes download.
Setting It Up
You need to perform a few simple tasks to prepare a scheduled iTunes download. First, go to System Preferences > Energy Saver and press the “Schedule…” button. Check the “Start up or wake” check box and select the time for your Mac to wake. You want it to wake at least 1 minute before your Calendar event will fire, to ensure that you are connected to the Internet. Once you have set the wake day and time, click OK and close the Energy Saver window. (continue…)