In this instance, you'll need to create the even to occur every 12 months, not every year. However, it's not set as default calendar ("My Calendar" is empty) and so I cannot see my appointments in the To-Do Bar.
If you receive a warning the "Exceptions will be lost", see Changing the End Date on Recurring Appointments When you create a yearly appointment on that recurs on a pattern (eg 3rd Sunday), it may use the original date for occurrence, not adjusting each year.This is because Outlook & Apple don't support the same patterns.Signing out and back into i Cloud does an initial sync but new items and changes don't sync. Addin HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\Office\Click To Run\REGISTRY\MACHINE\Software\Wow6432Node\Microsoft\Office\Outlook\Addins\Apple. (The i Cloud add-in could also disappear following multiple uninstalls and reinstalls or after a failed install or update.) Export your registry before editing it. Addin HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\Office\Outlook\Addins\Apple. Open any event that has No end date and set an end date.
I recommend using 10 events for yearly events and 1 year for more frequent events.If the calendar view is set on High details, check your all days events for end dates.Set the i Cloud calendar to use a List view, add the Recurrence Range End field to the View and sort by it.After I deleted the keys below, I opened i Cloud and a dialog popped up saying I needed to repair i Cloud to work with Outlook. After repair and reboot, the addin is back and sync works again. These accounts support EAS (Exchange Active Sync) and will sync directly with the accounts OTA (over the air).