Hi joe_7399,
There are no cheers to be had on this mess. This statement from the Apple website '...if you are using Outlook 2016, you can access iCloud Mail, Contacts, and Calendars on iCloud.com. Support for Outlook 2016 will be available in a soon to be released update." seems to assume that we are doing most of our work on an iOS device and sit with it open to calendar and or contacts while working in Outlook 2016 to get work done. It is an empty and nearly arrogant statement for Apple iCloud Team at support to make. It is insulting that Apple's iCloud team or higher support and or administration have not escalated and moves this resolution forward for now more than 9 months and with more that 60,000 posts that go back to the problem in several different questions posted here in the self help discussions. Where is APPLE? Someone needs to send these issues and the chatter from these discussion up to the iCloud Team and whoever is t the higher management level in the APPLE Org.
This all worked seamlessly when I was still using Outlook 2013, with Windows 10 Pro and iCloud for Windows version 5. The only thing that changed with the install of Office 365 subscription and the desktop Office 2016 (Outlook 2016 - a full install so that Office 2013 does not appear on my system in anyway now.
My Brother in Law, an Android OS lover, has teased me for years that I use a Fruit Phone. Well, I have to agree with him now that my fruit phone cannot sync with my PC's Outlook 2016 calendar, contacts, notes and tasks. I really want Apple to monitor this post and send it to somewhere in the org that has some clout and can light fires under the people who solve these problems. My feedback question are never answered personally or in anyway on the support site that give me any sense that Apple iCloud Team is supporting us and knows what the critical problem is. FILE TYPES dropped by Microsoft used in iOS calendar and contacts. DROPPED! Why and more importantly, how does APPLE work around it for us so that syncing works? IS Microsoft playing corporation gotcha with Apple? If so, Apple has allowed it to affect tens of thousands of users and a number that grows as user of upgrade to Office 2016 and have not idea they are committing themselves to a disconnect in the important linking data used to do most business and personal communications and interactions.
Yes, I have a Fruit Phone and Tablet. My association with Apple is becoming a basket of rotting apples.