Calendars not syncing after watchOS 2 update?

Try updating your devices to the latest software versions, released today: iOS 9.1 for iPhone and watchOS 2.0.1 for Apple Watch:

Update the iOS software on your iPhone, iPad, or iPod touch - Apple Support

Update the software on your Apple Watch - Apple Support

Update fixed my problem with cal not syncing.

Upgrading my Phone to iOS9.1 and Watch to 2.0.1 fixed the Calendar sync problem from my managed phone containing an MDM profile.

I'm pleased Apple fixed this fault with the first available release. My watch is now actually useful again.

Regards,

Dan

I applied 2.0.1 this evening and I'm pleased to report that the calendar sync issue with MDM is revolved. Thank you, Apple, for fixing this. My watch is back out of its drawer and on my wrist again.

No such luck here. After 9.1 and 2.01, still no calendar events from Exchange syncing. It's not a managed device (MDM) but it is via corporate exchange. Glad some have it working, but still frustrating here...

I wound up getting a new Watch. It already had 2.0 installed. I decided to just enter Calendar events directly on my iPhone and not sync with Outlook via iTunes. Even though it is a pain to keep two separate Calendars (on my desktop and iPhone), at least the Calendar data is on my Watch. Then, Apple released 2.0.1. Now I don't know if I should risk going back to syncing my iPhone with the desktop. If I try syncing and it doesn't work, is there a way to restore the Watch to its "out of the box" state, not just erase the data I inputted? BTW, I do not have a corporate managed device. I am just using MS Outlook 13, off the shelf as a home user.

I do got apple calendar working again on my Watch after updating. Only Fantastical still remains empty. Anybody got a clue ?

After a long wait and frustration, Apple finally fixed my problem. I have both MDM and Exchange accounts in my iPhone and now it is working fine (so far...).

I had two pleasant surprises yesterday. First one, I worked with our IT group and had an MDM profile installed on my phone, and as soon as that was placed my Exchange emails started coming through on the watch. Not sure why a managed profile would now allow it to flow to the phone. Tt was on the phone as an non-managed account, not sure why only a managed profile allows it to the phone. Either way, it's working now. The only down side to the managed profile is that I now have to provide my iTunes password even for free items due to the restrictions in the profile. Good trade so I can have the entries flow to the watch.

Second surprise is that a member of Apple engineering called me to discuss this since I had a case previously, and they said they noticed that I was still having issues. Good to know that Apple is still roaming these parts!

Brilliant..... first time it syncs correctly but now when add something in any of my calendars (e.g.: by accepting a meeting) the Watch does not sync automatically... To make this happen I need to Reset Sync Data every time I add something in one of my calendars (MDM and Exchange). Anyone with the same issue?

rmatayoshi, I am experiencing that same problem.

Same here. Calendar FINALLY shows my events but Fantastical remains empty...

OS 2.0.1 did not fix my syncing problem.

I then did a clean install of the OS's on both my iPhone 6+ and Watch. Yep, set them both up as brand new devices. Guess what? Everything is working fine now. It was a real pain performing the clean install on the phone, but it was worth it.