iPhone Calendar no longer syncs with Mac & vice versa (direct syncing – not iCloud)

[Graphically]

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

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

In addition to this, after applying the security update to OS X 13.4 last week, a new message started appearing 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've tried creating new calendars on the phone and Mac, but these aren't recognised across the devices either.

Just to clarify, I don't use iCloud and never have done and I don't want to, (so please no iCloud related suggestions). I just want to be able to sync my calendar events locally between the Mac and iPhone like I've been doing for years.

Any suggestions for getting this working again would be great.

Thanks!

– I know that Apple removed then (after an outcry) reinstated direct syncing in a previous upgrade a few years ago, but I haven't heard that about Ventura.

 

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Oh well, maybe Apple have quietly disabled this feature.

 

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Ran OS X and iPhone latest updates today. Bug still exists. <sigh>

 

[Saturn007]

It was working in Ventura 13.3.

See https://discussions.apple.com/thread/254762165

Could they have screwed up what happens when “Show this iPhone when on Wi-Fi”?

See https://eshop.macsales.com/blog/85316-how-to-sync-an-iphone-or-ipad-to-a-mac-running-macos-ventura/

I assume you did a search within Settings on the iPhone for “sync” and came up empty...

 

[Graphically]

Thanks for the reply. Interesting and yes, this may have started just before I update to Ventura. I forget exactly, as it was around the same time.

I don't have "Show this iPhone when on Wi-Fi” enabled, but I may try it just to see…

I only connect via cable.

For some reason it seems to think that it is "iPhone is syncing Calendars over the air", whatever that is. As you suggest, searching settings for anything to do with 'Sync' hasn't provided anything useful. I even tried logging into iCloud (which I've never done before) just to see if there were any useful settings available, but they were all set to 'local' syncing - as in, not via iCloud.

It's really weird.

I'm at the stage where I'm thinking of resetting the phone and starting again. But I think that the issue might actually be to do with something corrupt on the Mac OS X side - perhaps a Calendar or Finder preference file?

 

[zahidazram]

I am having the same problem, and am very interested in the resolution as I also do not use iCloud due to privacy reasons.

 

[Graphically]

Sorry to hear that I'm not the only one.

I've tried asking on Apple's support threads and most responses I get tend to say "just use iCloud", which obviously isn't a solution. (And, as I said upthread, even signing into iCloud doesn't help).

I'm increasingly thinking that this is something corrupted (or a bug) at the Mac/OS X side. Everything on the phone looks as it should and it's OS X that seems to be getting 'confused' about what it should be doing.

 

[Mithlas]

I've also have been having this problem intermittently since Mojave (now I'm on Monterey). I'm only aware that after peer to peer calendar syncing from iPhone to Mac, my Mac's calendar is missing some newer events from my iPhone. But usually I don't check my calendar events after a routine sync/backup. But when I do check, sometimes important dates have not transferred from my iPhone to my Mac's calendar. Currently, my only solution is to alter a minor thing in the missing event in my iPhone, then start syncing to my Mac. Then it appears in my Mac calendar. I have no idea why it wouldn't sync from the earlier version of the event. But I only do this 'fix' if I notice the problem. I think I have dozens of events that have not been synced properly over the years.

I prefer not to use iCloud Calendars after unintentionally causing all my iCloud synced calendars to delete certain important events. Luckily I had backed up my Mac calendar and could use it to restore the previous recorded dates (after disabling iCloud syncing).

 

[FlowerFan]

Did anyone ever get this to work again? I've tried syncing calendars using iCloud and it was a disaster. Duplicated and multiple events chaoitically all over my devices, so I've deleted all events in iCloud. I even tried logging into the Cloud to correct my calendars there, but the next sync still was a disaster, so I really would prefer syncing through the Finder over a cable. However, I'm not using iOS 18 and MacOS Sonoma and the macOS calendar wont sync with my iPhone. The option still looks like it's there, but nothing happens.

 

[FlowerFan]

Did anyone ever get this to work again? I've tried syncing calendars using iCloud and it was a disaster. Duplicated and multiple events chaoitically all over my devices, so I've deleted all events in iCloud. I even tried logging into the Cloud to correct my calendars there, but the next sync still was a disaster, so I really would prefer syncing through the Finder over a cable. However, I'm not using iOS 18 and MacOS Sonoma and the macOS calendar wont sync with my iPhone. The option still looks like it's there, but nothing happens.

So, I am going to answer my own post, here. I did several things and got the sync to work. I re-started my iPhone 12 Pro, but the sync of calendars still failed. Then I went to the info tab in the sync window on my macBook Pro and changed the Calendar settings away from All Calendars to Selected Calendars, but then I selected all my calendars. THAT WORKED!