shared calendar - new entries don't show up when 1 person adds

Hello Chenks,

Have you had a chance to review: If your iCloud Contacts, Calendars, or Reminders won’t sync - Apple Support

Things to check first

1. Check the system status of iCloud Contacts, Calendars, or Reminders to check for services outages or connection issues.

2. If a reminder isn't showing up on some of your devices, make sure that your iPhone and iPad have the latest version of iOS or iPadOS, or that your Mac has the latest version of macOS.

3. Make sure that you're signed in to iCloud with the same Apple ID on all of your devices. Then, check that you turned on Contacts, Calendars, and Reminders in your iCloud settings.

4. Check the date and time settings on your device to make sure they're correct for your current location.

iOS 13 and iPadOS or later

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

Restart the Contacts, Calendar, or Reminders app

1. Close the app.

2. Return to your Home Screen.

3. Wait about one minute, then open the app again.

Refresh your contacts and calendars

To refresh your contacts, open the Contacts app and swipe down on the list. To refresh your contact groups, tap Groups in the upper-left corner, then swipe down on the list. 

To refresh your calendars:

1. Open the Calendar app.

2. Tap the Calendars tab.

3. Swipe down on the list to refresh your events.

Check your app settings

If you use multiple groups or accounts in the Contacts or Calendars app, make sure that your iCloud Contacts and Calendars are set to appear:

- Open the Contacts app and tap Groups in the upper-left corner. Make sure that All iCloud is selected.

- Open the Calendar app and tap the Calendars tab. Make sure that all iCloud calendars are selected. 

Change how often your calendars update: 

1. Tap Settings, then tap Calendar.

2. Tap Sync.

3. If All Events is selected, choose a specific timeframe instead, like Events 1 Month Back. If a specific timeframe is selected, choose All Events instead. 

4. Return to your Home Screen. 

5. Wait a few minutes, then open the Calendar app. Tap the Calendars tab, and swipe down to refresh.

Since the iCloud Birthdays calendar updates daily, changes to birthdays might not appear in the Calendars app until the next day.

Are you using any type of security software or VPNs on this particular device? As these may block connections to Apple's servers: Check VPN (Virtual Private Network) and third-party software to help resolve network connectivity issues - Apple Support

Looking forward to hearing back from you soon, cheers.

Salutations Chenks, 

This is great isolating. It seems like the events aren’t pushing from their device to iCloud. Do you know if events they add to their own, private calendar are syncing with iCloud? They would find that out by signing in to the iCloud website and checking that calendar there. 

A next step we’d recommend would be to have them toggle Calendars off and then on again in Settings > their name > iCloud. However, if they have events added to their calendars that are not syncing with iCloud those events may be deleted. So please make them aware of that. They should be given the opportunity to keep synced events on their device though when turning off Calendars. 

Something else to check is whether both devices are up to date. That can be verified in Settings > General > Software Update. 

Thanks.