watchOS 5 and Outlook 365 Calendar not syncing

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

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...

Same issue here on watchOS 5.0/5.0.1 (on a Series 3) and iOS 12 (iPhone X). My work recently switched from their own exchange server to exchange online, same issue with both.

Things I've tried:

- Hiding the exchange calendar in the watch settings.

- Removing and re-adding exchange calendar account on iPhone.

- Unpair and re-pair watch both as a new watch and restoring from backup.

- Resetting watch sync data.

- Above with powering down and starting up both the phone the watch.

None of the above has worked.

More alarmingly even just having the exchange server just the iPhone (Exchange calendar disabled on the Watch via "Custom..." calendar settings in Watch app), sync is unreliable for the other iCloud services such as Reminders. A newly setup Watch when the exchange server is an account on the iPhone lead to my iCloud reminders did not sync over. Adding a reminder on the Watch leads to _data loss_ because the new iCloud reminder goes into a black hole and never sync'd. Completely removing the Exchange server (iCloud + Gmail accounts only) on the iPhone fixes sync, reminders and calendar events sync over, and new reminders on the Watch are synced to the iPhone within seconds.

My theory: there is a sync daemon, either watchOS or iOS, that is dying somewhat through processing the Exchange server account (i.e. this isn't just limited to calendar events) so there is sporadic/unreliable syncing of some Exchange account data and some other account data. Some other services no longer syncing with the Exchange account on the iPhone, duplicate partial calendar events when I changed the Exchange calendar color, and long sync times for the few data items that do sync have led me to this conclusion.

I have exactly the same problem. Try all solutions including reset watch, delete iphone account. All doesn't work.

Finally I found a solution: Ditch Apple calendar and use Outlook app which comes with watch integration. Works like a charm. Funny that Apple cannot make its calendar sync with watch reliably but Microsoft can.

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.

Did everyone install the watchOS 5.01 update that came out late last week?

Since I installed that, my watch is showing all events - this could just be a fluke (maybe the problem is intermittent and will come back?), and the release notes did not mention any fix for the calendar, but I think it's worth doing the update.

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!

That leads me to believe one of those events (likely a recurring one) which is showing up on the watch must be causing the sync to get stuck and that is the reason no other events (or changes to existing events) are reflected on the watch. That was the same experience I had until I lucked upon the one causing the problems, deleted it and then everything worked exactly as expected.

as astonishing as it may seems (and thanks to previous posts in this thread) I deleted a recurring meeting that was the only one actually showing on my watch and BOOM... all my meetings are now showing on my watch with all my 4 color coded calendar.

Now I can't even recreate my problem and probably that Apple will close my case... they won't have anything to test now

All nice to know, but in my opinion there is for sure a big in Watch OS 5.0/5.01 that is causing all the hassle. See the evidence: I have two Apple Watches connected to the same iPhone, one is an Apple Watch 1 on Watch OS 4.3.2, and one is an Apple Watch Series 3 on Watch OS 5.01. The latter has the problem, whereas the Apple Watch 1 perfectly syncs all my calendars completely.

Sounds as if we are fighting symptoms only when it comes to orphaned Exchange calendar records... the OS 4.3.2 can handle that right out of the box, where OS 5.0.1 fails to do...

I have opened my case about 3 weeks ago and referenced to Apple support about 10 other cases referenced in this thread.

After sending multiple logs, installing support/analytic provided by Apple support senior staff software on my phone, my watch, I have a confirmation from a senior engineer that is a software bug. There are no workarounds and Apple support told me it is now in the "pile" of bugs and goes by priority and expect to see a fix in upcoming iOS and/or watchOS update. Apple told me they have all they need now to proceed on fixing the bug, it is a matter of waiting now

same for me. Watch series 2 with watchos5, iPhoneX ios 12.

Even calendar app from Apple does not sync at all.

TinyCalendar works so the problem is definitely the calendar app on the watch.

OK, so here is what I believe is happening - there are "invalid" calendar entries stored in the Exchange server, and the iPhone and watch are not syncing them, and are hanging trying to sync them.

Have you ever had the following:

* Calendar invites that you can't accept/deny and make go away. They just stay there forever?

* Calendar entries that you can't get out of 'tentative'???

* Calendar entries that show up on ipad/iphone but NOT in Outlook?

So here's what I have - I have a free App Store app that lets you forward calendar entries that I wrote several years ago, and I just added a function to delete calendar entries. I went through all of my calendars, found those "messed up" meetings, and deleted them in my app. Syncing has been working perfectly since then.

Not sure this will work for everyone, but I have a test flight beta of the new version available now, and am submitting a final version to get on the App Store this morning. Let me know if you want to give it a shot!

Jeff

One other option would be to open your IOS calendar after step 2 and also go into the settings on the Watch App and Reset Sync Data under "General/Reset/" before going back into CalMate. I likely did that after turning off my Exchange calendar IOS settings so I could get my watch to properly sync my IOS calendar. Ultimately, I was left with all my normal calendars not showing any Exchange data, yet CalMate still showed the one orphan entry. After that was deleted in Outlook, I was able to turn everything back on and it was working as expected. No issues since last night with a number of calendar changes so believe, as Jeff stated, there is something still residing on the Exchange server that needs to be cleared out for the Watch complication to function properly. Best of luck - I personally know how frustrating this problem is.