watchOS 5 and Outlook 365 Calendar not syncing

Wow, indeed you did find the solution! At first I couldnt find the Outlook app adjusting the Watch face in the app. But adjusting on the Watch itself did the trick. And now it works! Thanks!

Strangely, mine started working at the end of last week within the native app. I didn't make any changes - i just noticed it started working. So far it's continued to work - so fingers crossed.

Here's another awesome side effect of this problem....

Mine started magically working again as of this morning. No changes on my end. Assuming the backend issue has been resolved. Anyone else working again?

Nope, not here.... still just as broken as before

Same problem.. no soultion ... outlook calendar in total random mode. Apple support ask to uninstall the app .. re sync the watch, blablabla

I hope they will find fix asap.

Yesterday my calendar was correct for today.. And this morning just few appointments only appears. Very Strange. I can't trust my watch for my meetings ... 😟

I would love to try..nothing else has worked. What is the name of the app?

I didn't even hear about the bricking issue until after I posted above. I am glad I dodged the bullet on that one.

well I installed Watch OS 5.1.1 and still NOTHING, we are at square one since the beginning on this issue.

Anyone tested as well?

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.

My take : I have wiped and reloaded my Apple Watch series 2 multiple times, and have had poor to no sync with Calendars. I put the same image on a series 4 and "it just works". I have put several hours into this issue.

So: A) My series 2 is bad and is under AppleCare. Do I get a new one and try again? Is the 2 even still available or will Apple give me a series 3?

B) The series 2 is not sufficiently supported by WatchOS 5 for a basic function of a smartwatch. My Pebble could keep my calendar.

In either A or B, it's a defect. Apple support was scheduled to contact me yesterday afternoon. I did not hear from them. I expect no news is bad news.

FYI - The series 4 watch came with 5. Calendars worked immediately. Updated to 5.01 and it still works.

Ok. I worked my way through support to the point where an engineering escalation was opened, the case number is 20000006714137

They will contact me back next week with next steps, but the sentiment I got is that the issue is being taken seriously due to the steps and findings I posted above. Fingers crossed.

Incidentally, while I was on the phone my wife asked me what I was doing. Turns out she has the exact same problem (at a completely different company with completely different back end systems - not even O365 but standard Exchange) and was just chalking it up to bad IT on her end. Confirmed identical behavior via the same steps on her devices.

Thanks orangejon. Your testing matches what I've found and suspected too (crashing sync daemon on one end, unclear if iPhone or Apple Watch, but rebooting iPhone is needed).

I haven't seen this mentioned by others, but for me the Reminders also won't sync fully or instantly when this bug occurs. I checked through diagnostic logs on the iPhone, (Settings -> Privacy -> Analytics -> Analytics Data) and I have noticed multiple eventkitsyncd.cpu_resource-* logs. The logs note incidents of high amount of cpu usage for eventkitsyncd on the Apple Watch, and the timestamps match when I've had the Exchange account added. Since EventKit is the framework for syncing calendars and reminders specifically, it makes sense that reminders are affected too when this bug happens.