Launch Files & Applications on a Scheduled Date with Calendar for Mac OS X

Apr 15, 2013 - 11 Comments

Calendar app icon If you have ever wished you could schedule the opening of a specific file, or set an application to launch on a specific date, either on a one off basis or on a recurring scheduled event, you can actually do both right in Mac OS X with the help of none other than the default Calendar app. Opening files and apps on a Mac at scheduled times is an astonishingly useful feature that is largely unknown, but it’s extremely easy to use.

We’ll cover how to launch specific files on a schedule, or just an application. Just like a standard alert or event, you can create repeat schedules with these as well. If you’ve ever created a generic event or Reminder in Mac OS X before, this is quite similar, except of course you are scheduling the opening of a file or application on the Mac instead.

How to Open a File on a Specific Scheduled Date

  1. Open Calendar in Mac OS X and create a new event, either by clicking the [+] plus button or by double-clicking on any date
  2. Pull down the menu next to “Alert” and choose “Open File”
  3. Open a file on a set date

  4. Directly under the alert menu, pull down the next menu and choose “Other…”, then use the file browser to select the file you want to open on a schedule
  5. Schedule the launching of a file

  6. Choose “Done” when finished

Use the “Repeat” function to set the file to consistently relaunch on the given date and time provided. These can be standard, or custom repeating schedules like every last Friday of the month.

The repeat feature is an excellent additional trick for repetitive tasks that use the same file, like a weekly or monthly earnings report, tax document, expense sheet, or whatever else requires regular use on a scheduled basis.

Once the date arrives, the selected file will launch automatically in the default application at the date and time specified in Calendar as the alert. Because it uses the default app, you would have to change the file-app association to adjust which app the file opens in, or just go the route of having the alert launch an application directly instead.

How to Open an Application on a Scheduled Date

This is more or less the same as the above trick, but you’ll select an app instead of a file to open at the scheduled time:

  • From Calendar in Mac OS X, create a new event, and pull down the “Alert” menu
  • Choose “Other…” then locate the application to launch and choose “Select”, the application can be in the primary /Applications/ folder or elsewhere, anything with a .app will work
  • Click “Done” to set the scheduled app launch

Keep in mind that with Mac OS X’s newer ability to restore saved windows, documents, and application states, that just setting an application to launch will open the app with all documents last used available. That will happen unless the feature has been disabled manually. This is different than using the “Open File” trick outlined above, which will open the specified file instead.

These scheduled events will sync with iCloud to other Macs and iOS devices, and though the iOS devices will get an alert on those days if one has been set, the app-opening ability will only work on the MacOS and Mac OS X side of things as iOS doesn’t (yet) have a similar functionality built into it’s alerts. Interestingly, iOS does have the ability to create the custom repeat Reminders through Siri though, suggesting it wouldn’t be terribly difficult for Apple to include this very useful ability in iOS down the road if they chose to.

Heads up to CultOfMac for finding this excellent trick


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Posted by: Paul Horowitz in Mac OS, Tips & Tricks


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  1. Cory says:

    Anyone know when this will be fixed? This workflow in Calendar is NOT working for 10.12.4

  2. scott says:

    No idea how to edit existing in Mavericks, but I have just tried to set up a new event to open an app.

    Alert> Custom > change ‘message with sound’ to ‘open file’
    Change ‘Calendar’ to ‘other’ then select the app from the finder window that opens.

    *note in attempting to replicate this, I had to quit calendar to get the finder window to open for some reason.

    • Eric Mazzone says:

      This is useless on Yosemite too. Set up a repeating event to open a particular file EVERYDAY, and it only runs once, then OS X, like a politician drops the file from the reminder the next day. EVEN THOUGH I check each event over the next two weeks to ensure it followed through!

  3. howard Goodman says:

    This has also stopped for me. Any ideas how to get it to work in Mavericks?

  4. Char says:

    Has this worked for anyone in Mavericks? I have tons of automator items connected to my calendar to get things done at work while I am away. Everything broke down, when I upgraded. Any suggestions?

    • Cam says:

      Yeah me too. The file doesn’t stick when saving the calendar item in Mavericks. It just defaults back to open ‘calendar’ rather than ‘file type’ every time :(

  5. JJM says:

    Clivex…. What a great solution! Never would have thought of doing it that way.Thanks, I’ll try it out later

  6. JJM says:

    This is a great tip and one that I’ve used in the past. There is a downside though and it’s this: If you have more than one Mac and it’s synced to your other Mac thru the Cloud, both Macs will preform the same function. For example, I used this tip to open up all my applications I use at work on my work computer before I got there in the morning (just to save time). However, all those same apps opened up on my home Mac at that same time and I didn’t want that to occur. Then, when my kids got on the computer in the morning they were screwing up all my work apps.

    • clivex says:

      I had the same problem, minus the kids.

      Is there any way to create a local calendar? Any new calendar defaults to iCloud.

      • clivex says:

        Found out how to make an ‘On my Mac’ calendar in, er, Calendar.

        Unselect any iCloud calendars in the left bar. If you have a subscription calendar, select that. If you don’t have a subscription calendar, hide the iCloud calendar list by mousing over the iCloud heading then clicking on ‘Hide’.

        Right-click in an empty area of the left column and select New Calendar. This automatically creates a new local ‘On my Mac’ calendar. Name it, and create any file or application alerts in this calendar.

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