Apple Watch Calendar not Syncing to Watch Face

Adding myself to this list. I have tried all the suggestions multiple times and, while some resolve the issue temporarily, my calendar doesn’t sync to my watch. Another process that sometimes works is going to your watch app on your device, tap ‘General’, tap ‘Reset’, tap ‘Reset Sync Data’. It will appear to do nothing when you tap it but evidentially it goes and re-syncs your calendar and contact data from your device. Also, it may take a little time to fully sync so you may not see your data immediately on your watch. Again, this worked a couple times but reverts back to no events on the Apple Watch again.

I am on Series 5 watch with latest updates. I have even joined beta program to see if updates in beta have resolved the issue and so far it hasn’t. :(

Having a similar, but slightly different issue. Have an IPP11 and a S5 watch. If I use the Calendar app on my watch, I can see all my iCloud Calendars on the watch/complication. But, if I use any third party calendar app, they can see my calendar events on the phone, but the apps on the watch cannot see the iCloud calendars. After testing, noticed there seems to be two type of iCloud calendars. One strictly in the cloud, and one that’s copied on the actual phone. What I found is if I toggle the iCloud Calendar switch to OFF in the iPhone settings, I get asked “What would you like to do with the previously synced iCloud calendars on your Phone? KEEP ON MY iPHONE or DELETE FROM MY iPHONE”. If I select KEEP, it creates a local copy of my iCloud Calendar entries, and then suddenly, the apps can see all the calendar entries. If I look at the calendars available in the Apple Calendar App, it now shows ON MY IPHONE listed above my iCloud Calendars, instead of showing them with an ICLOUD header. However, when I go to turn the settings switch back on, it asks me if I want to merge iCloud with the local copies, and when I do that, they all disappear from my watch again (except from the Apple Calendar app).

So the watch is not able to see iCloud calendars that are truly housed in the cloud, and which aren’t saved locally on the iPhone. I suspect this might be what is going on for everyone else as well. Test it out by turning of the switch, and then selecting KEEP, and see if the events show up on your phone before you turn the switch back on.

I have had this problem on and off— both with iCal and Google Calendar. I've had to unpair my Apple watch 4 a number of times which is a real pain, but then it syncs and displays my calendar events which is the main reason I got this watch. Interestingly enough, Google calendar syncs more reliably than ical.

I have been able to get it work from time to time.

However, in the middle of the day yesterday (18AUG2020), all of my events disappeared from my watch. Now, I did keep getting alerts; however, I did not show any events from my O365 account.

It is showing Apple Calendar (e.g. iCloud) events.

I cannot keep unpairing and re-pairing my Apple Watch, as it takes too long, and is not even close to a solution.

I am trying (again), the shorter solution of:

1. Turn off Calendar (O365) in iPhone
2. Reset Sync Data
3. Restart iPhone
4. Restart Apple Watch
5. Turn Calendar (O365) back on
6. Pray really hard

Hallelujah, it worked... I actually was typing this while doing the process...

Now, how long will it last???

I am not sure why Apple does not take this issue more seriously.

@Apple - please fix this soon.

Yes, my fox is to copy all events to the gmail calendar then it syncs. Any other calendar won't despite doing the many things suggested. Any fix is temporary. So while it is annoying to copy the events it is better than not having them on my watch.

To my surprise Calendar started to sync.

I guess it is because of Reset To Default and re-pairing

I keep my fingers crossed :)

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"?

Full reset as new or reset and restore from backup. When I restore from backup, I still have the issue. Was really hoping not to have to reset up the watch completely.

I tried Calendar 366, Calendars (by Readdle), and Fantastical. All three with the same results. At first, I thought it was a bug in the main app I use (Calendar 366), and even was working with the dev to diagnose and test beta versions he made just for me to try to track it down. Then I realized it was an apple bug when the other apps did the same thing. All except for the Apple calendar app.

I am still having no luck too, but one thought I had: Maybe it's an issue with MDM (Mobile Device Management) iPhones? Are others like me on MDM phones? If you look in Settings > General > Device Management you can see if this is the case.

@drdunga1 - I wonder if you are on to something here. I have a MDM setup from my work on my phone, and I’m having the issue where the calendar events will not show. I’ve tied it back to the watch not being able to see iCloud calendar events unless I’m using the stock calendar app on the watch. 3rd party calendar apps on the watch cannot see the events.

i thought this was resolved in watch os 6.1.1 - I got almost 5 days with the events showing perfectly but overnight the “no events this week” is back. have submitted feedback to Apple (you can create a shortcut to open feedback on non beta versions) I hope some other people having this issue could submit feedback this way as I don’t think Apple read these forums.

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).

Regrettably, I am using google calendars. It doesn't seem to matter anyway. Both iCloud and Google calendar data are suffering from this issue. Since my re-pairing of my watch it seems to be…better. But it's only been a few days.