Calendar woes. yet again

Annnd we’re back,

Calendars on my Mac are fine but even forcing a mac overwrites calendar on the iPhone or iPad does not put new data onto either iOS device. The last good data on any iOS device is from 2 May.

To reiterate, I WILL NOT use iCloud for this stuff. I sync only via cable. I have verified that nothing is supposed to sync via iCloud on any device.

I still have a bunch of Siri found in apps, reminders, found in natural language, and the default work, and home calendars showing up in my iTunes list. I have them unchecked for this synch sicne I have yet to figure out how to delete them that sticks.

Done all the same things I did before, clearing the preferences etc.

Anyone have any consistent way to get calendars to sync properly via cable from Mac to iOS that last more than a few weeks before going tits up?

Are you opposed to iCloud in particular, or just any cloud sync?

I had numerous problems with Calendar sync years ago so I then-reluctantly moved to Google Calendar, but it’s been amazingly rock solid for me, and Apple Calendar on Mac/iOS sync perfectly fine to it by subscribing to Google calendars.

iOS calendars all sync fine as well - most sync to Apple Calendar’s data [which polls GC], although my Readdle Calendar logs in directly to Google), so all my app widgets work without my needing to use a Google app (although Google Calendar on iOS is surprisingly good). And the customizations (eg push notifications x minutes before every meeting on my Work calendar) are more powerful than Apple’s.

If you use Gmail, Google Drive, or any other G Suite services, you already have access to Google Calendar through any web browser (often through 1-button access), and it’s faster and more powerful than Apple’s implementation in iCloud.

Apple’s privacy is of course superior, but Google places no ads on GC plus they don’t access any data for advertising purposes if you are going through a GSuite account.

We have the same stance wrt calendars and cloud services and our inadequate network connection makes using most cloud services a challenge anyway. Unfortunately it’s been a long time since I’ve been able to get calendar sync via cable to work robustly. The last time I tried I ended up with three stubbornly persistent copies of our main shared calendar on my phone. I haven’t tried recently because I’d thought that Apple long ago stopped working on that feature. Since we’re very Mac-centric we just use BusyCal for LAN sync and the iOS devices do without. Blah.

So I don’t have a solution but I feel your pain and would love to see one.

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No cloud sync unless it runs on our own servers and is controlled by us. So google calendar is out as well.

How about installing a Synology NAS and run their Calendar app?

You can have it available on your LAN only or if you need remote access setup a VPN.
This way you have full control over your data.

BTDT and it so totally hosed my system that I couldn’t even get calendar running AT ALL. See previous calendar problem thread I posted here

You could look for an encrypted calendar to connect to. Any combination of app and server that supports CalDAV format would do. For example: the native iOS calendar app with NextCloud, which is open source.

Or the encrypted calendar associated with Posteo, which offers anonymous email/calendar services.

Or Etesync, which has encrypted web app (no iOS, but they do have an Android app), and works with the calendar app of your choice (eg Google Calendar)

I’ve seen multiple postings that imply that syncing calendars via iTunes/cable is no longer supported. I don’t know for sure if that is true.

The Mac App Store has an app called SyncMate Plus; apparently there is a free version at I know nothing about either one.

SyncMate looks interesting, and calendar sync is included in their free tier.
They’ve been on Twitter since 2010, so must be doing something right.

No cloud outside our servers whether encrypted or not. Sorry, it’s just a no-go for us.

We had the Synology running the CalDAV server and were pretty far along but I could never get it to work with my Mac Calendar and syncing iOS. That was the start of the massive calendar disaster outlined earlier.

Mac Calendar is perfect for my needs, simple and provides what I need but the intermittent inability to sync to iOS is maddening.

FYI, you might be interested in this new thread in a privacy-oriented subreddit:

Thanks, I’ll try to get to read it this week, been dealing with a sheep disaster the last couple of days. It all ended yesterday though.

And in an update, I managed to escalate the problem to get a live Apple support person to screen share and of course the da**ed thing worked perfectly. I did delete all the calendars out of the reminders app though and that got rid of the excess “Siri found in apps” and “Found in natural language” calendars that were bothering me.

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