sync calendar/contacts with iCloud versus iTunes

I have not tried this program yet, but have heard good things.

https://www.companionlink.com/iphone/outlook/

It purportedly does a real "sync".

I can now report the same as @JohnF48. After reading their post, I updated my iTunes to 12.11.4.15 this morning and my calendar items still synch just fine.

@Dave_Beckett

Not sure if this will cover that warning, but ...

Edit > Preferences > Advanced: Reset All Dialog Warnings

@hlap: yes - photos, contacts, calendars

iTunes 12.12.2.2 released, but it appears to be mostly security patches. The warning is still present, and syncing the calendar still works for me.

I just went to 12.12.2.2 with 15.2 and sync still worked for me on iPhone and iPad.

As of 21-June-2022 --- iOS 15.5 with iTunes 12.12.4.1 still Syncs with Outlook.

I may be off base here, but I am thinking Apple wants you to use iCloud for Windows to sync. I have never heard of using iTunes for syncing anything but music stuff????

iTunes 12.12.7.1 with iOS 16.2 using MS Office/Outlook 2019 still works in synchronizing calendar and contacts in both directions

iOS 16.3 with iTunes 12.12.7.1 and Outlook 2019 still syncs just fine with Contacts and Calendar.

iTunes 12.12.10.1 with iOS 17.0, able to sync local Outlook.

I am beginning to get very disappointed in Apple. One of the MAIN reasons why I went with an iPhone in the first place many years ago is because I could sync my contacts and calendar with Outlook - both ways!

What alternative is there to sync contacts & calendar with Outlook 365? The Cloud is not an option for me.

Losing the built-in hardwire connection to sync an iPhone to a Windows computer would be a huge disappointment. The process works so reliably - in my experience - with Outlook Calendar and Contacts. If Apple discontinues this capability I hope someone can develop a work-around. I am not comfortable syncing my personal information via the cloud, regardless of the data security assurances that Apple (or any other provider) may provide. There's too much history of data breaches, whether intentionally mined or accidentally released through carelessness. Apple - please listen to this segment of your users: preserve the ability to sync to/from your devices through a wired non-cloud means. Please!

You can sync directly from an Android phone to your PC using a third-party app. Problem is, you have to run your Android phone in developer mode for that to work. I don't know if that situation has changed since I used a Samsung phone, but I will be looking into it when it comes times to buy a new phone.

Having the sync capability for personal info as a part of iTunes makes perfect since it is also used to sync the photos and music. Why not for the calendar and contacts too?