Issues moving from iTunes calendar syncing to iCloud

Alan, I haven’t found any benefit using even the 5 GB for anything except my mail at and my contacts. I tried using it to sync iCal when that stopped working in iTunes (even though iTunes still says it does when I sync my iDevices) but that was a disaster! I ended up with 4 copies of each event in iCal on my iMac and in my 3 iDevices - took me days to clean it up. Maybe if syncing of calendars worked, I would use it more but I’m not paying Apple just for them to cause similar disasters.


My wife suffered the same. iCal syncing (over USB with what used to be iTunes) totally screwed up her calendar between Mac and iPhone — entries got quadruplicated. It’s shameful that with $250B in the bank and more engineers on the payroll than many a town has population something as simple as this cannot be made to work. Even worse because as we all know until not long ago it worked just fine. Yet they had to break it along the way and couldn’t be bothered to fix it because, hey, syncing with a Mac is so yesterday. Today it’s iCloud and pay pay pay. No, it’s not about greed at all. Never.


Simon, that was the reverse of my problem. I never had a problem syncing via USB with iTunes. I use on my iMac as my SOURCE calendar and just synced it to the Calendar.ipa on my iDevices but at sometime iOS stopped updating the Calendar.ipa on my iPhone and 2 iPads so I tried syncing via iClod and that is when it went to hell. After I got on my iMac cleaned up, I went into iTunes with each iDevice and deselected Calendar syncing then reselected it. I then went and selected each calendar I wanted to sync, and enabled the option to replace every calendar on the iDevice with the one on my iMac. Wonder of wonders, that worked! So now, when iTunes doesn’t update the Calendar.ipa data with a normal sync, I just use the overwrite option.

Having a lot of engineers isn’t always a solution. These cloud sharing applications seem to be having a problem with updating. Say that I have some data on my iPhone which I create.This might be photos, calendars or files. It then needs to go to the cloud, and appear on my several computers etc. so then I decide to change it on my iMac. If it all works correctly then everything else gets updated. The problem seems to be that at times this fails and there is no updating or multiple copies are created. I don’t edit files on iCloud Drive because it is very flaky, so I never know if I’m working on the current version. DropBox seems not to have a problem.

It’s shameful that with $250B in the bank and more engineers on the payroll than many a town has population something as simple as this cannot be made to work.

Making sure that data synchronization works is not simple. In one of my many unsuccessful Apple job interviews, not covered by an NDA (two interviews were not unsuccessful and are covered), the hiring manager mentioned the topic, and I started to estimate how much testing his team must be doing to get it right, and all the infrastructure it must require. Awkward silence.


I doubt that was it because I’d unchecked the Calendar sync option in iTunes, but it could have left a glitch behind. However, I’ve been burned a few times by Apple changing things so I’m leery of changing. As I said to Simon in a reply yesterday, I’ve found that enabling syncing of selected calendars in iTunes then using the replace option in the Advanced section seems to work. Once I had on my iMac cleaned up (it took several days to find all the dups & figure out how to eliminate all but the original), doing the replace action took care of the problems on my iPhone & iPads. I think for now I’ll leave well enough alone. My iMac is a mid-2011 and is limited to High Sierra and iTunes 12.8.3 so I’ll wait until I have to replace the iMac and revisit my options then.


That worked for my wife too, initially. After several hours she finally had her Mac calendar cleaned up to the point where she could force overwrite the calendar on her next iPhone sync. That worked.

Except, it only lasted until the next sync. Then things got screwed up again. Also, as of lately, her once a year appointments got turned into once a week or once a day. It’s a friggin mess.

And seeing how she threw many hours out the window for a grand total of ZILCH, her conclusion has been to just stop having synced calendars. Now she squints her way through the iPhone calendar even when she’s working on her Mac. And this in 2023. On a $3k notebook and using a $1k phone. Supposedly “premium” kit. It’s preposterous. :man_facepalming: :roll_eyes: :face_vomiting: :face_with_symbols_over_mouth: Apple’s software reliability is in shambles. It’s not just the Six Colors report et al., it’s palpable even to a regular Joe such as myself with no special requirements whatsoever. (Except perhaps, for asking for this audacious sacrilege of avoiding cloud when systems under personal control can get the task done.)


I’ve never, never been tempted to move contacts, calendar, or email to iCloud. The first two stay on Google and have synced flawlessly across my devices for about 12 years now, despite occasional tussles with Google authentication schemes. The third is on a private ISP account that runs me about $60 a year for a full range of virtual server services.

This area is one that Apple never seems to have cracked.


Setting up a Mac Mini as a server recently clarified for me the following generalisation which I know to be true: iCloud on macOS is substantially responsible for much of the grief experienced in the Apple ecosystem. iOS gets the love; even iCloud Drive is more reliable on that platform. But Mac? It’s vestigial technology. Use it in its native and most comfortable habitat: local operation, except for third parties who take the business seriously, and applications that speak natively using commodity protocols like Mail and Calendar. But not anything that relies on the bewildering array of daemons and agents and other infrastructure that talk Apple’s protocols to Apple’s infrastructure. Even the Windows iCloud Drive support seems more competent to me. Sadly, as long as iCloud is a cost centre for Apple, iOS will always have preferencial support for it and local iTunes/Finder sync (also vestigial) won’t be as reliable (when it isn’t being actively sabotaged). It’s all very sad, but my clean, lean Mac Mini server is an absolute joy to use precisely because I’m not worrying about which part of Apple’s cloud integration has broken down again, or whether I’ve been logged into something I don’t want, or some obscure dialog box that I need to deal with in an unattended environment because it’s using some sort of privileged mechanism to bypass the notifications preferences to warn me about something or other or present one of those security codes. They simply aren’t made for one another.