watchOS 5 and Outlook 365 Calendar not syncing

Been on the phone with Apple support this morning. Have done everything asked including un pairing and repair with restore from backup. Nope. Next, Erase Apple Watch Content and Settings, set up as new watch. Still no. Delete Calendar from the phone, redownload from app store. No better off than before. I set a notification for an event I cannot see. When the notification occurred, i could then see the event. Dismiss the notification and now back to no events today or upcoming. Under general, Usage, Calendar and Reminders, there is 5.1 MB of data used. So there is data making it to the watch.

Next it goes to Apple engineers after moving through senior support.

The app is CalMate, and it's on the App Store, but for the 'delete' feature, you need the beta version.

Here's a link to the TestFlight beta (not sure of the apple forums rules - hope I'm not breaking them but hey, if so, I'm sure I'll find out!).

You have to install the TestFlight app, then re-click this link to get my beta. After installing, do this:

Launch app

Select 'calendars' and pick your Exchange calendar

Then, there are a couple of things people have done that have worked.

1. find any 'bogus' calendar entires - those that are stuck in your calendar inbox, those that hang when you select them, etc., and delete them

2. A user said this worked - after selecting your exchange calendar in CalMate, go back to iPhone --> settings and DISABLE your exchange calendar. Switch back to CalMate, and he had one meeting that still showed up, which was the one that iOS isn't handling properly. Go to Outlook/OWA and delete that invite, and re-enable the calendar on your phone.

Couple quick notes - I have a new beta waiting for Apple approval that fixed two bugs in this version:

1. I don't reload the calendar in CalMate after you delete a calendar entry, so even though you deleted it, it will show up in the app. You have to kill the app and re-launch. This will be fixed as soon as Apple approves the new beta.

2. The delete calendar dialog box had default text in it - this is also fixed in the next version.

Let me know if you can find the calendar entries messing up synchronization!

Jeff

https://testflight.apple.com/join/x0Y0y7dq

I also have the same problem, though our company is still running Outlook 365 on premise (i.e. not in the cloud). A few things I noticed:

• this morning I had all the exchange appointments in my watch calendar, a few hours later they were gone with a few exceptions.
• Funny enough, even after de-activting the exchange calendar on my iPhone and - obviously - on the watch app, those few appointments left were still in the watch calendar.
• Weekcal, another calendar app I use, does not work either

This app completely fixed my sync issue. Essentially, I had one "invalid" Exchange calendar entry which appeared no different than any other calendar entry within the Outlook app, IOS Calendar, etc. To fix the problem, I did the following after downloading this app.

• Step 1: Make sure Exchange account calendar is turned on within "Settings/Passwords & Accounts"
  
• Step 2: Open this app and hide all calendars except Exchange
  
• Step 3: Without closing this app, go back to Settings/Passwords & Accounts & switch off calendar in Exchange Account (make sure to tell IOS to delete Exchange calendar entries off your IOS Calendar)
  
• Step 4: App switch/toggle back over to this app and see if there are any "orphan/invalid" Exchange calendar entries still present.
  
• Step 5: Delete/decline invalid Exchange calendar item via Outlook on Mac or OWA/O365 Web Portal
  
• Step 6: Turn back on Calendar within Exchange account within "Settings/Passwords & Accounts"

Prior to trying this, I had followed the same steps many of the others have mentioned, but no matter how many times I reset my devices back to the factory default and started over, this sync issue would occur as soon as I turned on my Exchange calendar.

I can now add/modify entries on either my personal IOS calendar or Exchange and all changes instantly show up on my IOS calendars and properly sync with the watch. Thank you Jeff!

Latest update: it works for me now (hopefully it will stay that way).

This is what I did as I had updated watch os to 5.1.1

I have to say my Phone is managed via a profile management from my work

I have an iPhone X ios 12.1 and Apple Series 2:

• Deleted the profile from work so phone becomes unmanaged
• Deleted all accounts on phone so calendar is empty
• Reset my watch as new watch
• Added all accounts except O365/Exchange account
• Tested- worked good. All calendars items showed on watch
• Added the profile management from work
• Added account on phone WITHOUT calendar (just Contacts and emails)
• Tested again - still work (of course no calendar from O365 yet)
• Added Calendar from options in Accounts on phone
• Did not show up right away.
• On phone added a test meeting on O365 calendar --> all calendars showed on iPhone
• Added calendar on watch and so far, everything is working as advertised...

Fingers crossed...

I have the same problem using my iCloud Apple calendar AND Outlook Exchange. Completely unreliable. Same watch series2, WatchOS 5 and IOS 12. Tried everything you did to attempt to fix. No luck. I DO get notifications for calendar appointments I can't see on the watch, but do appear on my iPhone 6s. I have tried mirror and custom for the calendar events, neither works.

It just does not work.

I have the same problem, but my employer sent out a notice last week that there are some known problems with Office365 and iOS 12 - they didn't say what specifically, but they did say Microsoft would update Office365 by next week to address the problems, and recommended not updating until September 24th (of course I ignored that warning, deliberately).

It's possible that this watch problem is related to the issues that Microsoft will fix soon.

That may be turn out to be the case for MS problems, as I believe 11.4.1 included a patch for Exchange. However, my iCloud calendar works no better than Office 365. I think there is an underlying problem which goes back years as some appointments sync, but not consistently. It "may" have been fixed in the past, but it's broken again. I will be contacting apple support tomorrow.

I have this issue as well and its extremely annoying.

Additionally I've tried restoring watch from backup (a watch os4 backup) which failed to restore the watch to OS4. I've also attempted to set the watch up as a new device vs from backup.

iPhone 7, iOS 12

Apple Watch series 2, watch OS5

Everything else mentioned above was also tried. No dice.

One thing that is interesting is that one 3rd party calendar app works perfectly fine. Tiny Calendar. Unfortunately it doesn't have a complication though which is 50% of what I need out of calendaring on the watch... but at least I can use this for reminders and as a workaround for everything else until Apple fixes this garbage.

I tried Fantastical (which has a complication) and it behaves the same as the native watch OS calendar app.

And I just got six notifications for one event (from my iCloud calendar). Meanwhile my employer says that the Microsoft patches are all complete for our institution, but I still can't see most events from Office365 calendars on the watch (though I do get those alerts) - so this seems to be unrelated to whatever other issues Microsoft was working on.

Meanwhile, everything is working fine. I didn't change anything at all, but now the syncing between exchange calendars and Apple Watch running Watch OS 5 is working flawlessly. I had 24me installed, which worked fine as well, but was able to de-install it on the Watch at least, now that the syncing works again.

so, whoever did anything to resolve the problem, thank you.

Same issue here, except adding Office365 calendar has now caused my personal iCloud calendar to stop syncing real time or reliably. Currently running IOS12 on iPhone Xs Max & OS5 on Watch Series 4. All events sync to IOS calendar fine; however, random results are shown on Watch calendar (tried unpairing and resetting watch, deleting and re-adding both iCloud and O365 calendar, etc.). Vital functionality and calendar appointment reminders are primary reason I purchased new watch.

I have dealt with 3 senior advisors now on this issue. Each of them has told me they don't check these forums. If you are having an issue with yours, I suggest you contact support at the top of the page. Thanks.