sync calendar/contacts with iCloud versus iTunes

This could be why:

https://www.macrumors.com/2021/01/05/outlook-for-mac-to-be-replaced-with-new-client/

Regardless, I will just not update iTunes when it reaches that version that removes the sync option to Outlook calendar and contact items.

This same here. I'm not backing up anything to any cloud, because security concern. I'm backing up my computer to external hard drives only. I don't understand why Apple is deprecating syncing contacts and calendar, it's ridiculous.

Lukeread2021 - thanks for the pointer to CopyTrans, but when reading through the website I can't find a direct reference to the ability to sync my contacts/calendar. There is mention of copying them from one device to another but no reference (that I can find) to actual sync'ing.

Do you know if CopyTrans does support true sync'ing?

That makes a lot of sense. I bet you’re right. Recently Outlook desktop running with the Microsoft 365 system that updates in the background had an error message that it couldn’t find the calendar. Some calendar features such as showing your daily schedule to the right weren’t working. A MS users support board had a thread like this complaining and quickly an official MS message was posted that said they were fixing it. Within about 48 hours that message disappeared and the features reappeared.

I think all of that supports the “Microsoft is the problem” theory.

BTW I was finally able to upload my calendar and my contacts properly to outlook.com after this iTunes issue started. Integrating them to the phone and desktop is another matter.

It does align with Outlook 365, but it doesn't make sense. There are plenty of us who have standalone copies of Outlook (MS Office) who don't need all the bells and whistles of the latest and 'greatest' MS Office suite.

When Apple forced people to use cloud-based Notes, I started putting my notes under my Contacts and further Grouped them under Notes or Recipes. Now, Apple is gonna jettison synching Contacts via Desktop MS Outlook?!

I'll convert one of my domains to have an Exchange Server - BlueHost offers that services - and synch my Contacts via the Exchange Server, if I have to. One way or another, if I have to pay someone for this feature, it will NOT be MS or Apple.

Many of the posts here have referred to syncing contacts/calendars from the desktop to the phone/ipad.. I usually go in the opposite direction.. and when I backup the devices I do it on my desktop and then manually backup the apple files (in the music folder) in Windows 10 to an external drive.. I guess my question is whether or not any of the solutions mentioned would allow me to keep on as I have been doing.. also using Outlook as part of Office 2007.. and one final and perhaps simplistic thought.. wouldn't this problem be solved by simply not upgrading iTunes? I managed to get a copy of version 12-10-10..

My fear is Apple do something on the device side when updating iOS that stops its syncing with older versions of iTunes to force people to upgrade. I think due to security exploits and patches, you have to update the phone OS really. Keeping an old version of iTunes is what I am doing for now, but fear this option will be taken from me at some point due to device updates.

I also have the need to two ways sync, i mainly use Outlook on my desktop, but there are times I add contacts and appointments on my phone and these need to sync back.  

I think Microsoft is just looking to use web technologies and have a single version for different OS rather than force users to the cloud, but there is not a lot of detail out there. They have a massive number of organisations (government and private) that use desktop outlook and can’t / won’t move to cloud. Microsoft will not want to lose that enterprise revenue.

If CopyTrans is dependent on Apple and, somehow, iTunes for its product to work, I am curious why anyone used their product in the first place all the while iTunes [currently] does that same synchronization?

As for the reference to AOL, Dave, this will not hurt Apple. I think we Outlook users - particularly the ones who (a) won't use the cloud, and (b) use iTunes tethered to our phones thru a PC cable/wifi - are barely a blip on their radar.

I emailed CopyTrans support and they confirmed back their product uses iTunes to work and they said there is a real risk it might stop working when iTunes removes features (i.e. it’s no better than staying on an old version of iTunes). I can see no reason to install right now as doesn’t mitigate the risk.

If it works post the iTunes upgrade, then great, but its not ideal for giving anyone certainty.

APB1966 - agree that the impact of we (comparatively) few users that have to use a non-cloudy solution consisting of less than 100% Apple will not hurt Apple.

My comment was more to point out that this type of "the company knows best" thinking is what cripples large companies and diminishes their utility. That approach inevitably leads to the point where competitors start to make significant inroads on what was a very solid & loyal client base. At the end of the day, a company needs it's customers far more than the customer needs a specific company.

I have the same issue. It’s been working just fine for over a decade. So why doesn’t Apple offer any other solutions?

I called Apple support and they didn’t even know about this issue.

Apple must NOT get rid of this function!

I like and trust Outlook. It’s better than any other mail app. It is my standard and go to program for calendar and contacts and email. So Apple needs to recognize that this is the case for many and taking away a critical function is not the right thing to do. Besides, I trust my local back-up and I do not want a paid for cloud backup.

My experience syncing outlook with cloud was horrible. Duplicated the contacts many times and there were additional issues with calendaring as well. I would not recommend it. It took many hours to fix the problem.