Warning: iCloud Calendar invitations have unpredictable behaviors

I suspect few people use iCloud Calendar invitations -- or else we'd all know about this. It's not a new behavior, it was first documented in 2011. It's still true.


It's important to know about this.


When you send an event invitation to an email address iCloud will look up the person associated with that email address (possibly using Contacts). If that person has an iCloud email address then the invitation will go to their iCloud calendar. No email will be generated. If they don't actually use that iCloud calendar they will never see the invitation.


If the invited person does not have an iCloud address in contacts then an email will be generated.


So if you invite with a gmail address, and iCloud finds an iCloud address associated with the gmail address Contact, no email will be sent to Google Calendar. Instead an iCloud Calendar event will be created.


There is such a thing as being too clever.


Some details are here: http://apple.stackexchange.com/questions/27449/icloud-calendar-not-sending-invit es/29970

Posted on Jan 21, 2016 6:53 PM

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14 replies

Jan 22, 2016 7:25 AM in response to jfaughnan

In further testing I thing we've established that the rerouting from the original invitation email to an iCloud account occurs not via the recipients Contacts data, but rather by an Apple server lookup against Apple ID records.


Note that


1. An Apple ID is always associated with an iCloud calendar, but may be associated with multiple secondary email addresses.

2. Many people have multiple IDs that they've unwittingly created and don't know about. (I know of 4 associated with me.)

3. Apple IDs cannot be merged (Tim Cook said 4 years ago Apple was working on this.)

4. I believe one can now have an Apple ID that does not use a .me or .icloud or .mac domain.


Given all of the above it's no surprise that the behavior of an iCloud Calendar invitation is only somewhat predictable if you use a .me or .icloud email address for the invitee.


This has been true for 5 years, so it's unlikely to change unless Apple does a radical overhaul of iCloud Calendars. There are no rumors of that.

Jan 22, 2016 5:34 PM in response to jfaughnan

jfaughnan wrote:


I suspect few people use iCloud Calendar invitations -- or else we'd all know about this. It's not a new behavior, it was first documented in 2011. It's still true.

Seems like this is not new -- iCloud calendar doesn't send invitations to Gmail users...


When you send an event invitation to an email address iCloud will look up the person associated with that email address (possibly using Contacts). If that person has an iCloud email address then the invitation will go to their iCloud calendar. No email will be generated. If they don't actually use that iCloud calendar they will never see the invitation.

Can confirm this, i.e. when I've sent an invitation to the wife, it will show up in her Calendar with the option to either accept or decline it, though as you mentioned, no email to see the actual invitation.


If the invited person does not have an iCloud address in contacts then an email will be generated.

So if you invite with a gmail address, and iCloud finds an iCloud address associated with the gmail address Contact, no email will be sent to Google Calendar. Instead an iCloud Calendar event will be created.

I couldn't try this, however give me a couple days to do so, and will return to provide results.

Jan 23, 2016 3:49 PM in response to zinacef

I did some experiments using a gmail account I know is not associated with any of my Apple IDs.


In this case iCloud does send an email for both updates and invitations. It shows up in my Gmail account. There are no attached .ics files though, so Google doesn't handle it the way it would an Outlook invitation. It's a web form, when you accept you are taken to iCloud where an .ics file is available for download.


Curiously an update to a multi-day appointment did show up on Google, probably something to do with message text.


This fits with theory that for past 5+ years iCloud has been trying to look up iCloud Apple IDs based on associated emails, and if it finds one it redirects the invitation to an iCloud account that the recipient may or may not use -- or even be aware of.

Jan 23, 2016 6:25 PM in response to jfaughnan

jfaughnan wrote:

This fits with theory that for past 5+ years iCloud has been trying to look up iCloud Apple IDs based on associated emails, and if it finds one it redirects the invitation to an iCloud account that the recipient may or may not use -- or even be aware of.

So, are you saying (only trying to understand the crux of it so forgive my naiveté) that sending a calendar invite, from an iCloud account, to someone who doesn't have an iCloud account will only result in an email-type of invitation? The invitation will not show up in their calendar but only as an email? Did I get it right?

Jan 23, 2016 6:30 PM in response to jfaughnan

Oh, it's much worse than that.


It all depends.


If the invitee gmail address is associated with an AppleID database, then an event will be created on the iCloud calendar associated with the matching AppleID. No email will be sent.


If the invitee gmail address is NOT associated with an AppleID database, then an email will be sent to the gmail address. The email will not be recognized by Google as an invitation.

Whichever happens, there is no event created on the Google calendar. In the 2nd case the recipient is at least aware of the invitation and they can create an event themselves.

Not one Apple user in a hundred understands the AppleID to email relationships and not one in 1000 knows all their likely AppleIDs...

Jan 23, 2016 10:20 PM in response to jfaughnan

jfaughnan wrote:


If the invitee gmail address is associated with an AppleID database, then an event will be created on the iCloud calendar associated with the matching AppleID. No email will be sent.


I was able to mimic this with the wife - she saw the invite in her iCloud calendar and only there.


jfaughnan wrote:


If the invitee gmail address is NOT associated with an AppleID database, then an email will be sent to the gmail address. The email will not be recognized by Google as an invitation.

I was also able to mimic this with my son. He saw the invite in his Gmail address, Google Calendar, and no other place.


jfaughnan wrote:


Not one Apple user in a hundred understands the AppleID to email relationships and not one in 1000 knows all their likely AppleIDs...


I'm guessing what you're saying is there are inherent issues with iCloud calendar along with associated Apple ID's?

Jan 23, 2016 11:03 PM in response to jfaughnan

jfaughnan wrote:

...

4. I believe one can now have an Apple ID that does not use a .me or .icloud or .mac domain.



There are two reasons that you should never trust a calendar invitation to work between any provider to any other provider. The ONLY time you should expect it to work is within a specific technology domain such as users that are ALL within a single organization that uses a single Calendar server.


1) Per stated in (4) above, the email address that is very loosely related to any given AppleID has nothing to actually do with the AppleID account. The username of every AppleID is (unfortunately) an email address that the user has provided when creating the account, yet is has NOTHING to do with the AppleID nor the email/calendar provider. Therefore, there is absolutely no way for Apple to know if the email address that is provided when creating an AppleID actually has any capabilities to receive calendar invites. In the most obvious example, just because I use a .iCloud account when creating an AppleID, doesn't mean that I either use iCal or that I even have iCloud Calendar enabled at any on any of my Mac OS or iOS devices. It's a very troubling issue that nearly all "cloud"/Social service providers use a provided email address text value as the userID of their accounts. I boggles my mind why cloud/social services every thought that having a persons unrelated email address as a username for an unrelated service was a good idea. For example, why in the **** would Google, Apple, Microsoft, Facebook want to allow a user to have a username of "xxxx.aol.com"? It makes no sense to even the most knowledgeable users and completely confuses all others! I'll say it one more time, using email addresses as username makes no sense at all but it seems that Apple along with all the big players are still doing it so we are stuck with it.


2) Even in 2016 standards for email, calendars, and contacts are still unstable and can;t be trusted for interoperability. Anyone that insists on still using client applications for email, calendars, or contacts in 2016 understands that painful reality that IMAP, CalDAV, and CardDAV or vCard are still far from standards that actually WORK across clients. The reality is that they don't and you should expect that exchanging such information between clients will never work reliably as long as providers insist on using proprietary interpretations of "standards".


Therefore, there is no solution to expecting that iCloud calendar invitations will ever work as expected unless ALL the users involved are within a managed domain that has a controlled Calendar client environment (i.e. all of your users are using Apple devices and Apple servers). Otherwise, the only trusted solution is to send an email with the meeting details instead and allow the recipient to add it to their native calendar server via their native calendar client.

Jan 24, 2016 9:07 AM in response to zinacef

Apple's iCloud is actually working as designed. The problem is the design choice was very poor.


Most of the Apple geeks I know think iCloud invitations are simply unreliable. That's not true. They are instead reliably unpredictable.


They are unpredictable because the iCloud rerouting vs. simple messaging is both undocumented and it relies on data that very few users understand (Apple ID configuration).


The fix is "simply" to remove the cleverness -- to make iCloud calendar invites simple but predictable. So invitations sent to an iCloud address (.me, .icloud) should create Calendar events, otherwise create an email invite. No mysterious lookups. [1]


The invitation should also include an iCal attachment. Apple does that now, but ONLY after clicks on the calendar email invite message and accepts. If the invite includes an iCal attachment Google and Microsoft Calendars will process it.


[1] One wrinkle is that one can actually have an iCloud Calendar, contacts, notes, etc WITHOUT an email address. I had one of those. I think Apple's iCloud Notes, Contacts, Calendar run on a different system from their email. I wonder if this kludge arose because Apple doesn't have a clean server-side relationship between iCloud email and iCloud Calendar. So to fix Calendar invites they have to fix deeper issues with their identity infrastructure. Which would explain why it's been "broken" (very poor user experience) for five years.

Jan 24, 2016 9:17 AM in response to FishingAddict

I largely agree with you, but as noted in a separate response to Zinacef I think Apple could go from being reliably unpredictable to reliably predictable. Changing the workflow around sending the iCal attachment would, as you note, make the email invite route much more useable.


The use of an email address as the de facto unique identifier of the 21st century deserves more attention. Email is mutating from a human communication tool to an identity management/crude transactional exchange system. I'm writing a book about supporting special needs teens and adults with smartphones, and one of the 'aha' moments was realizing how management of email connected with delegating identity.


I wonder if Apple may have some legacy issues on the Apple ID side with the relationship between their iCloud services, their identity management server, and their email servers that may make it difficult for them to know which iCloud email address is associated with which iCloud Calendar. I get the feeling they have a lot of cobbled-together legacy systems they are slowly migrating to a more integrated architecture. I'm glad I don't have that job.


Although Microsoft (Outlook), Google and Apple have taken divergent approaches to Calendaring the most recent iCal standard (CalDAV I think?) still does 90% of the job. Certainly a vast improvement over Apple's currently reliable but unpredictable approach.

Nov 15, 2016 4:13 PM in response to jfaughnan

i cannot believe how long i have had this problem and not realized. there are 3 iphones in my family, and mine uses an @me.com icloud account, the other two are @gmail.com icloud accounts.


i have always wondered why my calendar invites have been ignored, and now i know they have never been received! i also learned that it does not matter whether i attempt the invite from my iphone or from my windows computer, which uses outlook 2016 but uses only my @me.com email account.


so here's my question: does anyone know a workaround? none of us can feasibly change our icloud accounts. i can receive their calendar invitations just fine, but can't send any.

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Warning: iCloud Calendar invitations have unpredictable behaviors

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