watchOS 5 and Outlook 365 Calendar not syncing

I’ve got the same issue. Series 4 watch on 5.0.1.

I’ve never had this problem before but suddenly big chunks of my exchange calendar aren’t going to the watch. All my iCloud stuff is there, and all the exchange events are there fine on the phone. I’ve removed and readded the account, reset the sync data, even wiped and repaired the watch and it’s still doing it.

Never had the issue before on my series 0, series 3 or even before 5.0.1 on my series 4. It’s brand new and really bothering me.

Nice. I’ve been in touch with engineering and provided logs and additional feedback, I’d be surprised if my input had a rapid enough impact to be in a current beta build however maybe it will help shore things up additionally going forward.

Fingers crossed and many thanks to Apple for listening to us.

Don’t know about that. I was working fine until I updated to iOS Public 4 last night. Now this morning I’m missing outlook entries yet again. Sorry to burst the bubble but I’m on this thread because the darn sync issue is happening. LOL

No fix for me. Installed 12.1 beta 4, no change in behavior at all on the watch, Exchange basically not syncing to the watch at all, everything still shows in the iOS calendar. Please fix Apple, it is killing me. 😟

This isn't exactly a solution... it's a workaround, and not really a great one at that. The Outlook app doesn't have a complication for the modern watch faces used on the Watch 4, and not having both my personal (iCloud based) and work (Exchange based) calendars merged into a single app doesn't actually provide the visibility needed to orchestrate a very busy schedule.

So far I haven't heard back on the logs I posted to Apple engineering, but I am staying hopeful.

Update: Nothing has changed for me. Recap: I have had an open case since Oct 24th on my Series 2 still under AppleCare until May 2019. Calendar sync not working for apple calendar, let alone new events in Exchange. On 10/1 I purchased a Series 4 at a local Apple Store. It worked great with my 6s. No problems with calendars, apple, exchange, google or hotmail. They all worked. However, I returned the Series 4 on 10/15. My reason for doing so was simple. I can't trust Apple to keep something working under AppleCare. Therefore why would I buy a new one and keep it? Will the next update/upgrade break it? Will Apple even so much as acknowledge there is a problem? Has Apple even hinted of replacing my series 2? No. Have they offered to send a test watch? Still no. The engineers might have an idea as to what's happening, but they aren't talking to me.

Well, it doesn't seem to be in any way hardware related. It appears to be a software issue and your experience with it working properly on new hardware was likely coincidental based on all of the other factors not ruled out in your test.

Well,I can confirm a couple of things. My calendars seem to be syncing now. Good. My Reminders are completely futzed. None of them sync to the Watch and creating them on the Watch via Siri shows them on the watch for a short time and then they "disappear" not to be found on either device.

I've tried the following and it still persists:

1) Reset Sync Data

2) Restart Each Device (one at a time and see, then both together)

3) Reset and Repair the Watch restoring from backup

I didn't try setting it up as new because I didn't want to have to re-do all my watch face complication settings and app installs (since I don't let it auto install all the companion apps). Now, the Notifications for Reminders show up on the watch with all the options (Snooze, Mark Complete, Ignore) and they seem to work but the actual items don't sync.

Grrr...

Well, I took the plunge and installed the iOS 12.1 public beta but no change... Though now I see this:

https://www.macrumors.com/2018/10/29/apple-releasing-ios-12-1-tomorrow/

So if that is right and 12.1 official along with a watchOS update hit tomorrow, maybe, maybe, it will have a fix for this issue rolled in.... :-/

My Calendar has been working for a while but my Reminders don't sync at all -- to the point if you create one with Siri on the watch, they'll show up there as the only reminder for a bit and then disappear later from the watch. They never make it to the phone. Reminders on the phone never show up on the watch at all (since the Calendar started working - before that they were sporadic like appointments).

So I got iOS 12.1 on my phone but didn't get watchOS 5.1 because it was pulled. It downloaded but didn't install as I was waiting for the overnight charge, and by the time I got there the release had been yanked.

iOS 12.1 has made no difference by itself in the behavior; still just sporadic reminders/calendar events. And while I appreciate the workaround that folks are offering in the form of the Outlook app/complication, that does very little to help those of us who maintain professional and personal schedules separately and need the native calendar in order to see the confluence of events for proper time management.

Will keep an eye out for the re-release of watchOS 5.1 and see if maybe I get any results there, but so far I'm not encouraged.

Thanks for the update and for time spent pursuing a fix with Apple!

I do have the same issue with missing calendar entries from an exchange server on Apple Watch Series 2 (Watch OS5), although they're reliably shown on IPhone 7 (iOS12).

experiencing the same thing and did also the same actions, didnt solve anything