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iPhone Calendar no longer syncs with Mac and vice versa!

I have been syncing my iPhone with my Macbook Pro peer-to-peer for ages (i.e. not using iCloud). These are not Outlook calendars or anything server/network related, just locally created calendars.


Since I upgraded to OS X Ventura, calendars of any kind no longer sync between the devices. The syncing process seems to go through the motions, but the calendars on the iPhone and the Mac don't update with each other's events. (Music files seems to sync fine, FWIW).


Since applying the security update to OS X 13.4 this week, a new message appears in the Finder iPhone window under 'Info' saying "iPhone is syncing Calendars over the air" and "Over-the-air sync settings can be changed on your iPhone."



I've looked on my phone, but I can't see anywhere that I can change these mysterious settings. I've no idea what it means, but it's not something that I have changed manually. I don't have an iCloud account and never have done and I don't want one. I just want to be able to sync my calendars locally between the Mac and iPhone like I've been doing for years. I've tried creating new calendars on the phone and Mac, but these aren't recognised across the devices either.


Any suggestions for getting this working again would be great.


Thanks!


(If the ability to sync locally has been removed, it would be nice if Apple let us know.)

iPhone 12 mini

Posted on May 19, 2023 10:47 PM

Reply
Question marked as Best reply

Posted on Dec 17, 2023 10:46 PM

Hello,


Since updating macOS Big Sur to Ventura in a family's 13" Intel 2020 MacBook Pro over a month ago and synchronizing two folks' iPhones (13 & 11 Pro Max's v16.7.2) in two different macOS accounts, I found issues with Calendar events in both macOS Ventura v13.6.x and iOS v16.7.x:


1. MacOS' Calendar shows missing new, deleted, and updated events from iPhones. How do I get all iPhone's calendar events to show up in macOS' Calendar? Is there a way to force it? I know it can go the other way, but iPhones will lose their newer data. :( And yes, I checked to see the calendars are selected (all enabled).


2. After the first synchronization for each iPhone after macOS upgrade, both iPhones and macOS' Calendars showed many duplicate events.


I did some research over the weekend and found out other users are having this problem too:

https://talk.tidbits.com/t/my-mac-apple-calendar-went-berserk-i-need-help/23878/39

Calendar sync to iPhone or iPad using USB… - Apple Community

Calendar synchronisation between iMac and… - Apple Community

iPhone Calendar won't sync with Mac - Apple Community

Sync Issue with my iPhone and MacBook Pro - Apple Community

Calendar synchronisation between Mac mini… - Apple Community

iPhone Calendar no longer syncs with Mac … - Apple Community

etc.


My family don't use iCloud for Calendar and others, except Find My, and any other non-Apple third party services and apps for calendars. All synchronizations are done through lighting-USB2 cables. Is there a known bug or something? Is there a workaround without using cloud services? Is there a way to force synchronize overwrite macOS' calendars with iPhone's?


Thank you for reading and hopefully answering soon.

14 replies
Question marked as Best reply

Dec 17, 2023 10:46 PM in response to whatdoesthistake?

Hello,


Since updating macOS Big Sur to Ventura in a family's 13" Intel 2020 MacBook Pro over a month ago and synchronizing two folks' iPhones (13 & 11 Pro Max's v16.7.2) in two different macOS accounts, I found issues with Calendar events in both macOS Ventura v13.6.x and iOS v16.7.x:


1. MacOS' Calendar shows missing new, deleted, and updated events from iPhones. How do I get all iPhone's calendar events to show up in macOS' Calendar? Is there a way to force it? I know it can go the other way, but iPhones will lose their newer data. :( And yes, I checked to see the calendars are selected (all enabled).


2. After the first synchronization for each iPhone after macOS upgrade, both iPhones and macOS' Calendars showed many duplicate events.


I did some research over the weekend and found out other users are having this problem too:

https://talk.tidbits.com/t/my-mac-apple-calendar-went-berserk-i-need-help/23878/39

Calendar sync to iPhone or iPad using USB… - Apple Community

Calendar synchronisation between iMac and… - Apple Community

iPhone Calendar won't sync with Mac - Apple Community

Sync Issue with my iPhone and MacBook Pro - Apple Community

Calendar synchronisation between Mac mini… - Apple Community

iPhone Calendar no longer syncs with Mac … - Apple Community

etc.


My family don't use iCloud for Calendar and others, except Find My, and any other non-Apple third party services and apps for calendars. All synchronizations are done through lighting-USB2 cables. Is there a known bug or something? Is there a workaround without using cloud services? Is there a way to force synchronize overwrite macOS' calendars with iPhone's?


Thank you for reading and hopefully answering soon.

Mar 1, 2024 2:14 PM in response to whatdoesthistake?

I have the exact same issue as the original poster, and several other posters:

  • I do not want to use iCloud to sync my calendars
  • I do not want to put any of my data at all on iCloud
  • I want to sync between my iPhone and my desktop Mac via cable, like I have been doing easily and successfully for many, many years.


I can add new entries on my desktop Mac calendar, and see them appear on my iPhone (15.8.1). But it seems like entries on my iPhone will not sync back to my desktop Mac (Ventura 13.6.4).


Did Apple really stop supporting such a basic function? If so, can someone please explain why???

May 21, 2023 4:46 PM in response to sberman

OK, let's simplify this further. I have never signed into an iCloud account. I've never used it, because I've never needed or wanted to use it.


But back to the issue that I posted about, which is that direct syncing between my Mac and iPhone has stopped working as it should. I just want to carry on being able to sync between the Mac and iPhone directly, as I had been doing until a few weeks ago when I installed Ventura and it stopped working.

May 31, 2023 4:59 AM in response to sberman

Thank you for your continued interest and contributions. However, as I have clarified, the posts you have made have not been on topic with regard to the issue I have asked for help about. While you are obviously entitled to your opinions, it would be greatly beneficial to the conversation if we could remain focused on the original question. This might also encourage others with pertinent insights to join in. I respectfully request your consideration for this. Many thanks for your understanding.

May 21, 2023 1:55 PM in response to whatdoesthistake?

Hi whatdoesthistake?,


Based on what you've shared the best steps you can take are found here: If your iCloud Contacts, Calendars, or Reminders won’t sync - Apple Support


Calendars and Reminders

To check which account your calendars are in, open the Calendar app, then tap the Calendars tab. 
Set an iCloud calendar as the default calendar:

1. Tap Settings, then Calendar.
2. Tap Default Calendar. 
3. Tap a calendar under iCloud to make it your default.


Regards.

Dec 9, 2023 12:23 PM in response to whatdoesthistake?

Two of my clients also don't use iCloud and any other clouds for Calendars, Contacts, etc. They do all their synchronizations via/through local lighting-USB cables. Ever since updating to Ventura from Big Sur about a month ago, it made duplicate Calendar events in both iPhones and macOS. Also, newer Calendar data don't show up in macOS' Calendar. :( I can't find any fixes so far.

iPhone Calendar no longer syncs with Mac and vice versa!

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