watchOS 5 and Outlook 365 Calendar not syncing

I just upgraded to iPhone X to iOS12 and Apple Watch Series 2 to watchOS5.


My Outlook calendar appointments are now NOT displaying on my Watch calendar app, though my iCloud appointments are displaying on the Watch calendar app. I have tried unpairing/repairing (Erase Apple Watch Content and Settings) multiple times, hard resetting iPhone, hard resetting Watch, "Reset Sync Data" on iPhone Watch app, unselecting Outlook 365 calendar on iPhone and then re-selecting Outlook calendar on iPhone. I've also ensured that the iPhone Watch app Calendar setting is set to "Mirror iPhone" for both Notifications and Calendar. Ironically, I do get my Outlook calendar notifications on my Watch, but no corresponding calendar item in the Watch calendar app.

Is anyone else having this issue, and if so, have you been able to resolve it? If not, what's the best way to inform Apple about this bug?

Apple Watch Series 2, watchOS 5, null

Posted on Sep 18, 2018 8:58 PM

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Question marked as Top-ranking reply

Posted on Oct 3, 2018 8:16 AM

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

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138 replies

Sep 25, 2018 2:15 PM in response to dwysocki

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.

Oct 1, 2018 8:17 AM in response to bkilimnik

My case is 100652226940.


This weekend I had removed calendars from my iPhone and did the swipe down to refresh. I then wiped the watch and started over for like the 5th time.


When I started the watch back up, old data reappeared for calendar entries no longer on the phone. I wonder if the problem lies with IOS not WatchOS.


Senior advisor has a call back scheduled for late this afternoon.

Oct 4, 2018 7:33 AM in response to dwysocki

I'm having the exact same issue, I'm relieved it's not just me. Just like everyone else, I've tried wiping synced data/resetting my watch multiple times now and nothing seems to fix it. I have two Office 365 accounts and both are afflicted with whatever is causing this. This is a pretty significant bug; I rely heavily on my calendar and my Watch to show up on time.

Oct 4, 2018 10:07 AM in response to dwysocki

Same story for me, and same results from trying the various suggested fixes. Deleting calendar entries to try and correct is not an option -- I have maybe hundreds of meetings in my Outlook calendar, many recurring. My loss of productivity would be unacceptable. Apple please address this ASAP as it is significantly diminishing the value of my Apple Watch right now. 😟

Oct 4, 2018 11:19 AM in response to dwysocki

My Case: 20000004766019


Apple will call me next week to troubleshoot before sending it up to engineering. They requested I open a helpdesk ticket with my Exchange admins... I am 99% sure they will punt it back to me (and Apple) since the calendar events sync fine with no problems in iOS. It is only from there to the watch that this breaks, i.e., I cannot see how this is an Exchange issue versus the watch miss-handling certain calendar objects. Please fix it ASAP Apple!

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watchOS 5 and Outlook 365 Calendar not syncing

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