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?
https://www.synology.com/en-us/dsm/feature/calendar

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

https://talk.macpowerusers.com/t/calendar-crashes-on-high-sierra/10828

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

https://apps.nextcloud.com/apps/calendar

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

https://posteo.de/en/site/encryption#addressbookencryption

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)

https://www.etesync.com/user-guide/

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 https://www.data-retrieval.net/data-transfer/how-to-sync-iphone-calendar-with-mac.html. 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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2023 Update

Calendar sync via cable stopped working completely with the Ventura emergency upgrade earlier this year. Same time the ability to create a PDF printout of a list view of longer than 15 days also died.

Currently at over 60 hours of direct phone/screen time with apple support and still no results.

I tried Busycal, horrible options for printing PDF calendars and still uses cloud sync.

I tried Fantastical, sync still a cloud service.

So is there any way to have a set of about 15 separate calendars on my mac that I can sync by plugging in my iPad or my iPhone to the machine and using the sync there that also allows me to print a full color list view of a months worth of calendar entries and a nice color month fiew as PDFs each month?

How about running your own CalDav server? A 2011 Mac mini handled 200+ email accounts and normally ran at no more than 10 - 12% CPU utilization. I wonder if you would notice a Caldav app running.

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I ask this as I am naturally curious, what is the reason for not wanting cloud sync? I am a huge time vs money person and I’ll happy spend money on a solution that saves me a significant amount of time. 60 hours on the phone with Apple support when using a cloud sync service that will solve all of your problems? Very curious as to your thought process here.

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I tried to get a calDAV server running on our Synology a few years ago totally unsuccessfully. But I think that either on the Synology or on my MacMini is the way to go as well. I just don’t need another project right now :frowning: but I may be forced into it.

Don’t trust iCloud at all, no security (built into the calDAV serve), don’t want personal and private data on a machine I don’t control if not fully encrypted which a calDAV system cannot be.

I am well aware of your no Cloud policy. But just in case Hades ever freezes over, it looks like you can accomplish all of the above, except syncing via cable, using a non-Gmail Google Calendar.

How can I access Google Calendar with a non-google email? - Google Calendar Community

Google doesn’t say how many calendars you can create but they do say “Do not create more than 60 calendars in a short period.” And since you can manage everything using a browser it is simple to print your calendars in color and make PDFs.

Avoid Calendar use limits

Print your calendar - Google Calendar Help

Should you ever need/want to export your information Google exports calendars in “iCalendar” format.

Export your data from Google Calendar - Google Calendar Help

Perhaps arcane, but what about going back to the last version of macOS and iOS that served this need reliably in the way you want? You could get an old Mac and iOS device running the appropriate versions just to serve as your calendar device. It’s almost like going back to palm pilot days.

As others have mentioned, short of hosting your own server, I doubt there are many modern options for what you want to do. The world has pretty much completely moved to cloud sync. I do struggle to understand the need to keep your calendar so secure. I can kind of understand the email part of things but you’re also just going to be sending emails to people who are almost all on google or Microsoft hosted email platforms so I’m not sure there’s much of a security or privacy benefit to self hosting.

I think if I were looking for a non-cloud option I would most likely return to a paper diary. This would probably save you the most time.

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