If your CollegePlannerPro calendar is not syncing with your Apple Calendar, the remedy is to unsubscribe, then re-add your calendar to Apple Calendar.
To Unsubscribe from a calendar, head over to your Apple calendar, and right click on the calendar you wish to remove, then click on Unsubscribe:
To re-add your calendar, copy the Apple Calendar link from within your CollegePlannerPro account, then click on the File menu within Apple Calendar, and select New Calendar Subscription:
When prompted, paste in your CollegePlannerPro calendar link.
Tip: The auto-refresh rate defaults to "Every Week". You'll want to change this to "Every 5 minutes" to ensure that you have the most up to date information on your calendar: