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Multiple iCloud services aren't syncing

I just discovered the issue this morning, but Calendars, iMessage, and Reminders are not syncing; Notes, however, are (I haven't tested Contacts, and I don't use Mail).


Calendars


I entered an appointment for today in iCal on my Mac (Mountain Lion 10.8.2) on Tuesday. I checked my iPhone (iOS 6) to see when the appointment was, and there was nothing there. I checked iCal, the appointment was still there. Problem is, it never made it's way to iCloud.com.


I ended up deleting my iCloud account from my Mac and reinitializing it, but nothing.


I created the appointment in iCloud, but it never synced to my Mac or my iPhone. Deleted it, then created it on my iPhone. Again, nothing.


iMessages


I checked iMessages, and here's a bit of an oddity: I sent myself a test message from the Mac, which I did appear on my iPhone. Cool. Awesome. I sent myself another message from my Mac a few minutes later, and nothing. However, in the list of messages on my iPhone, it shows the timestamp of the test message as when it was sent from my Mac, but when I went to view the messages on my iPhone, it still showed only the first test message. I sent another test, this time from my iPhone, and it arrived on my Mac. Another test from my Mac, and it came thru on my iPhone.


During this debacle, I was texting my girlfriend, but our conversation history during that time did not appear. The last message that shows up in iCloud is from this morning just past 9.


Notes


After reinitializing iCloud on my Mac, my Notes all appeared on my Mac. Wunderbar.


Reminders


None of my Reminders made it back to my Mac, and after creating a test one, it never showed up.


***


Does anyone have any idea why there is so much intermittence between iCloud, my Mac, and my iPhone?

Posted on Oct 18, 2012 10:09 AM

Reply
9 replies

Oct 18, 2012 1:42 PM in response to pvonk

Sorry, I should've mentioned that, but my Calendars were in 'iCloud', not 'On My Mac', and have been for some time.


[EDIT] Oh, and I had this happen to me while I was out and about: I left the aforementioned appointment in the Calendar on iCloud, and it eventually pushed down to my phone.


Unfortunately, the same cannot be said for iCal, as nothing has updated; it's still a barren wasteland, even with the refreshed iCal CalDAV account.

Oct 22, 2012 8:36 PM in response to Nintendo Tim

[Update]


Everything is now working, except Calendars from iCloud to Mac, and vice versa.


I did end up exporting calendars from the Mac side, and deleting all calendars from iCloud. Eventually, my iPhone and iCloud were on the same page, but here's the weird bit: even thought I deleted all calendars, every calendar reappared, but empty, save for two ('Work' and 'Personal').


I've signed out of iCloud on my Mac, then signed back in, but using my alternate @me.com email address already associated (I've seen this mentioned in another, similar article). That didn't work.


From my understanding, Calendars and Reminders are handled under the same instance (since it's labeled as "Calendars & Reminders" under System Prefs > iCloud. Why would Reminders sync, but not Calendars?

Oct 23, 2012 8:26 PM in response to Nintendo Tim

OK, this is getting pathetic:


iCloud and my Mac are now talking on all fronts, but rather than iCloud pulling Calendar information from my Mac, it's pushing all the empty data to the Mac.


I have a Calendar backup (thank Thor), and whenever I import that data, iCloud decides to write over it instantly.


I've gone to iCloud, and deleted all calendars that I can. I reimport the calendars on the Mac, and iCloud simply pulls the calendars themselves, but leaves the events behind, then it's deleted from my Mac.


Simply put:


How do I get Calendar to push the event/calendar information to iCloud, rather than iCloud pull calendars, then deleting events?

Oct 24, 2012 3:26 PM in response to Nintendo Tim

[UPDATE]


I have the solution! No thanks to anyone, with the exception of pvonk, who at least attempted:


Mac

  1. Export individual calendars from Calendar using Export > Export... (I created a keyboard shortcut using + E). Do not export as Calendar Archive; this carries with it iCloud data, which you don't want.
  2. Once each calendar is exported, sign out of iCloud in System Preferences, and have it delete everything; Calendar will remove the 'iCloud' section of calendar data.
  3. Reboot (yes, you must reboot).
  4. Once back, Import (again, keyboard shortcut == + I) each calendar individually, and make sure to choose 'New Calendar' each time. They will appear under the 'On My Mac' header; this is what we want.
  5. In iTunes, sync your iDevice (I only have an iPhone 4), but under [Info], choose to 'Sync Calendars' and opt for 'All calendars'. This will wipe the iPhone of all calendars, since there's nothing in Calendar. You may have to do this step with each iDevice you have synced to your iCloud account, but I don't have a secondary one to test.

iPhone

  1. Once the sync is done, go into your iDevice, and disable Calendars via Settings > Mail, Contacts, Calendars > Accounts - iCloud.
  2. Choose to delete the data.
  3. Re-enable Calendars, and choose to Merge.

    This will push all the calendar data to iCloud, which will prevent it from pushing empty data, overwriting perfectly good data on the Mac/iDevice.

iCloud (optional, but advised)

Log in, and go to Calendar. You aren't doing anything, but sitting back and watching delicious calendars and events get pushed from your iDevice to iCloud. This also allows you to ensure your iPhone is pushing the data.

Back to the Mac

  1. Sign back into iCloud via System Preferences.
  2. Calendar may kick back an error, saying it can't connect. Dismiss this - you may have to click the yield sign next to 'iCloud' - and it should sync.
  3. In iTunes, there's no need to disable 'Sync Calendars' under [Info] for your iDevice; this is taken care of when you sign back into iCloud and opt for calendar syncing.


And boom. There you go.


To solve this entire issue, that Merge option on the iPhone should exist on the Mac. Rather yet, iCloud should pull new data, not overwrite it.


Apple. Fix this. I don't want to spend days figuring this out. If I didn't have an iPhone, I'd be royally screwed.

Multiple iCloud services aren't syncing

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