How to fix disappearing calendar invitations sent from an iCloud calendar

I recently ran into an annoying situation where invitations sent using my iCloud calendar (from iCloud.com and from Calendars.app on OS X).

Let's say I'm inviting john@example.com to an event:

But, john@example.com never receives my invitation!

What is happening is that iCloud sends calendar invitations on the server side. So when you invite someone to an event in any iCloud client (Calendar.app, BusyCal, iCloud.com's calendar, etc.), the client creates the event with the invitation on the server, and then the iCloud server sends an email to whatever address you specify with the invitation (john@example.com in this case).

This works great except when John has added john@example.com to his Apple ID. (He might do this so he can send iMessages from this email address, for example.) If John has done this, the iCloud server that usually emails invitations decides that he must be using an iCloud calendar and the invitation goes straight into his iCloud calendar notifications. It is never delivered to his inbox as an email, like would happen for non-iCloud users.

Solutions

There are two ways to fix this problem, but unfortunately they are both on the recipient's side (there's nothing you can do as the event creator).

First, the recipient needs to go to https://applied.apple.com and look under "alternate email addresses" to see if his email address is listed here. If it is, there are two options:

  1. Remove the email address from the Apple ID (which may break other Apple services like iMessage using this email account); or
  2. Go to https://icloud.com, log in, click on the "Calendar" icon, click on the gear in the bottom left corner, click "Preferences", click "Advanced", and then change "Receive event notifications" from in-app to "Email to john@example.com".

Bottom line

If you use iCloud calendars to send events to people who do not use iCloud calendars, but might have associated their email address with an Apple ID, you have to manually check with them to make sure they received your event invitation. 😒

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