What to Do if Your Apple Watch Is Not Syncing to Outlook

Despite Apple’s attempts to make Apple Watch a multi-purpose device, the Calendar feature is probably the number one motivator for many who purchase this gadget. However, people who use their iPhone Calendars to manage their business or personal appointments often face problems with Apple Watch – either not showing appointments or displaying an outdated version of their iPhone Calendars. In either case, restarting iPhone or Apple Watch, or force closing the Calendar app, does not work.

The syncing problem first appeared in earlier releases of watchOS, but even in watchOS 2.1, it seems the issue is not fully resolved. This question-answer guide is designed to help you resolve the issue of Apple Watch not updating changes made on your iPhone calendar.

What if you create an appointment that displays on your iPhone Calendar but does not sync to your Outlook desktop Calendar?

Syncing Calendar on your Apple Watch with third-party apps outside Apple’s ecosystem can be tricky. While the first generation of Apple Watch supports only Bluetooth to transfer data, it can only communicate with apps like MS Outlook through iPhone. Thus when Apple Watch does not push appointments to Outlook, most of the issues are caused by the lack of 2-way syncing between iPhone and Outlook. As a result, in many cases, a stable 2-way syncing of your phone with Outlook is enough to ensure your Apple Watch will receive all appointments you made in Outlook and be able to push back the changes.

When considering software options for 2-way syncing of your iPhone with Outlook Calendars and Contacts, there’s no better solution than AkrutoSync (check out over 1k reviews here?) . You can start your free trial by verifying the program properly syncs iPhone, and simultaneously resolve your Apple Watch Calendar syncing issues!

Still having trouble? Let’s go further…

Sometimes Apple Watch cannot properly pull the data from iPhone. When this happens, outdated appointments appear in the Watch’s Calendar app. Some users try to manually delete these appointments hoping they will no longer appear on the watch, but unfortunately the events only disappear from the phone. They remain on the watch frustrating users who are unable to delete them. Sounds familiar?

Apple Watch can’t sync calendar data to iPhone

iPhone to Apple Watch Calendar sync issues may occur when you want 10 or 20 calendars to sync with your Apple Watch. It appears that some of the issues are a result of watchOS’s inability to handle syncing too many calendars to your device. If you can’t force your Apple Watch to re-read changes on your iPhone Calendar, you may try reducing the number of calendars you’re trying to sync with your watch.

What if reducing the number of calendars to be synced doesn’t work?

You may see some different solutions to syncing problems depending on the type of calendar or watchOS version, so let’s discuss some of the most common ones and see what happens:

• Changing the event to private and then back to public to re-sync calendar

  Unfortunately this method does not solve the problem of iPhone not pushing data back to Outlook. You should also be aware that if you have other invitees on your calendar event, it may cause your phone to send useless meeting update emails.

• Resetting the Watch to factory settings and trying it again? Think twice!

  If this is the way you think might help you with syncing Outlook Calendar on your Apple Watch – you’re wrong! By doing this you may lose all the settings you’ve created with other apps and you will not get anywhere with Calendar syncing.

• Unpairing and pairing it again is not working

  You could think it’s working, but, if you make any change to your Outlook Calendar, it will work smoothly with your iPhone but not with Apple Watch. This is still all about the way iPhone and Apple Watch are communicating with each other. If you removed all the calendars from your phone but everything is still on the watch, here’s what to do:

  1. Tap the Watch app on your iPhone
     
  2. Go to Settings and choose General
     
  3. In General, swipe down until you see Reset
     
  4. Tap on Reset Sync Data to erase Contacts and Calendar data from your Apple Watch
     

  Doing this erases everything you synced with iPhone and allows you to re-sync with new data. Don’t worry if you see no signs of re-syncing after pressing the “Magic button”; this process goes on behind-the-scenes (No, you’re not the only one who thinks Apple should add some warning).

Finally, here’s what to do when you don’t see the changes, or new appointments, on your Apple Watch that you’ve made on your desktop Outlook.

These simple steps work in 90% of cases:

1. Confirm that your desktop Outlook is properly synced with your phone; syncing through iTunes or iCloud can often cause a bottleneck for the entire process. Use AkrutoSync to ensure iPhone can reflect all Outlook changes.
2. Ensure your watch is properly paired and synced with iPhone. Try using apps that require Watch to pull information from iPhone; if everything appears fine, move to the next step.
3. If you have numerous changes to sync, give it a few minutes (it’s a Bluetooth, remember?).
4. If you’re still seeing outdated appointments, simply press the “Reset Sync Data” button.