Apple Watch Calendar not Syncing to Watch Face

Here is what finally worked for me:

Go into each account on your iPhone and turn off the Calendar.

Restart iPhone and Apple Watch

Turn on any iCloud calendars

Validate Sync occurs

Turn on Exchange Calendars

Restart iPhone and Apple Watch

Validate Sync occurs

Evidently, something in how MS does policies (or something) creates periodic issues with Apple Watch and syncing, messing EVERYTHING up.

Good luck.

What worked for me was making sure my watch was backed up to the cloud, unpairing my watch, and preparing my watch and restoring the watch from backup.

I have to unpair/re-pair my watch about every 2-3 weeks after it stops syncing. I have tried the other approach to remove calendars under Passwords & Accounts and then re-add - didn't work. Both phone and watch were just updated to latest iOS today.

I just can't understand why this can't be fixed. Everything posted here is a workaround, not a fix. Why should we accept these terrible "solutions"?

This may be premature, BUT, I MAY have figured this out. Before I did this, my watch was displaying “No more events”.

go to settings

go to passwords and accounts

Go to iCloud

Go to iCloud

Under “Apps using iCloud”, turn off the Calendars toggle, (don’t delete anything when asked).

Then turn it back on.

now, hopefully, it didn’t screw anything up with all of my synced and shared calendars, but so far, all I know is after I did that, my next calendar event showed up on my watch!

Well, fingers crossed. I am hoping my watch issue is resolved. Upgraded from an iPhone 7+ to an 11 Pro yesterday and added my watch as a new one. So far the calendar items are syncing perfectly. I spoke with several of the Apple techs at the store yesterday and they were not aware of the non-syncing issue. They all had Apple watches too. I'll report back in a few days or so on status.

I have the same issue. The calendar syncs for 1-2 days then just stop synching. Then slowly over a day or so certain events come back - sometimes it's recurring meetings. Sometimes it's one calendar. Sometimes the entire thing. I'm not sure what's going on, but my guess is this is some problem with Apple's underlying sync mechanism. I've tried the following to "fix" this:

1. Turning off/on iCloud calendar option
2. Using the Reset calendar & contact data in the Watch app settings on my phone (that never works)
3. Removing the number of calendars in my master calendar. Not just "not synching" but actually removing the calendars from my watch/mac so i only have 5 calendars synching (work, personal, TripIt iCal feed, and my son's sports iCal schedule feed)
4. Unpairing & full reset of my watch

Not one of those items work. I'm on an iPhone8 (latest iOS update) and a Series 5 Watch (latest watch OS update).

Here are the steps I've taken to reliably fix this issue (twice now) with the Siri watch face not showing upcoming events. I've tried many different combinations of steps taken from various articles and posts, but the only reliable steps that have worked for me are the following (#6 is key):

1. iPhone: Settings > Passwords & Accounts > iCloud > iCloud > Turn Off Calendars…
2. Choose “Keep on My iPhone”
3. Restart iPhone and Apple Watch
4. iPhone: Settings > Passwords & Accounts > iCloud > iCloud > Turn On Calendars…
5. Choose “Merge” existing calendar events
6. iPhone: Watch app > General > Reset > Reset Sync Data
7. Wait a minute or three for everything to sync back to your Watch

[My devices: iPhone X (iOS 13.4) and Apple Watch Series 3 (watchOS 6.1.2]

PS Thanks to everyone who has contributed to solving this terribly neglected problem thus far... Hopefully there will be a fix for this in the future.

Good luck!

I called Apple Support and finally got it to work. Here is what I had to do:

https://support.apple.com/en-us/HT203521

Here was the critical step for me:

OS 13 and iPadOS

After each step, check your contacts, calendars, or reminders. 

Refresh your contacts and calendars

To refresh your contacts, open Contacts and swipe down on the list.

To refresh your contact groups:

1. Open the Contacts app.
2. Tap Groups in the upper-left corner.
3. Swipe down on the list to refresh your groups.

To refresh your calendars:

1. Open the Calendar app.
2. Tap the Calendars tab.
3. Swipe down on the list to refresh your events.

Add me to the list :( I have tried all fixes above: iCloud sync, unpaired watch, factory reset watch and I still only see a few random events on my watch. Nothing new shows, only older re-occurring meetings. So frustrating

After few weeks I can say that once or twice a week the watch stops to sync with the calendar. After half a day to a day it starts to sync again. I couldn't find a good reason why it stops to sync or what it starts to sync again.

I am having the same exact issue with my watch, I called Apple support last week and opened a ticket. I've tried everything to resolve this on my own, the only calendar that is populating on my watch is my work Exchange account. My account through Google, with multiple calendars, is not populating at all. I'm glad to see that I'm not alone and really hope Apple can resolve this issue through an update, my watch is almost useless without the calendars.

Add me to this list. :(

I have a brand new Series 5. I have the calendar on my Infograph Modular watch face and it keeps freezing. It happened yesterday - froze on the last meeting of the day. So I re-synced me calendar today. Everything was fine for a few hours. Then it froze again after my last meeting.

I thought it had something to do with the notifications? I tried to disable all the notifications except for meeting reminders because I was getting notifications for everything (invites, replies, etc). Once I 'customized' the notifications, that is when I started having troubles. Has anyone else noticed this?

I keep having the same issue off and on. I have a series 5 with an iPhone 8. All updates have been installed. I have toggled the calendar on and off, I have removed my email accounts and resynced. I have restarted both my iPhone and the watch. It seems to work for a bit but then starts missing calendar events. The last time I went through this process I had meetings at 8, 9 and 10. The 9 am meeting was displaying on the watch, but no other appts. then I resynced everything, now only the 10 am meeting shows. What is going on?

I have the same issue. Working great up until yesterday. Now, it only shows a couple synced entries.

I've tried restarting my watch and iPhone, re-syncing data, force restarting.

I just erased my watch and set it up as a brand new watch, and it still doesn't sync the calendar events.

I have an iPhone 11 Pro, Series 5, iCloud and Exchange accounts.

Very frustrating!

Having this also. Complication showing events but tap on it shows “No more events” message.

Been on the phone with Apple support who also advised previously suggested fix of iCloud sync. This did not work for me. The only fix that does work was to delete and reinstall the calendar app. However after a couple of day’s the problem returns and I’m back to “No more events” or “No events this week”

Driving. Me. Crazy.

Calendar is one of the main reasons I use Apple Watch. such a useful feature shame to see it crippled by a simple bug.