New iPhone Air this fall. For several years, iCloud and Outlook on Windows PC has been a total disaster. Losing contacts, losing phone numbers and/or in the wrong fields from the last big fiasco, where Windows Outlook changed field names or something. It continues to be very flaky! Recently, discovered that a contact that has been there for years suddenly has no phone #'s Last two weeks, Outlook blue refresh button kept displaying Bad Password. I am totally sick of this BS and I am done. I have not found a reasonably easy fix for all of this, in several years. At times it worked but when it didn't work, the fix was to touch dozen of settings in multiple apps, etc. and many times nothing fixed it. But some days, it got better for some reason.
I don't blame Apple for this. I think it is all a Microsoft problem. Maybe its time for me to dump Microsoft completely and get a Mac desktop. But, I know Windows to well after all these years and not looking forward to make that change...yet.
You want a great solution? Put contacts and calendars at Google and sync it to Outlook and to your Apple devices and just FORGET about using iCloud for the task. It goes to your Apple devices perfectly and it still goes to Outlook contacts and calendars. So you can add easily add contacts to emails, etc. Been flawless so far.
Outlook email still works as normal.
Only downside I've discovered is that you cannot add calendar items nor contacts in Outlook. In Outlook, the setup for the PST file, you delete iCloud completely. But you can use your Apple mobile devices to add new Calendar items or modify Calendars items. And you will get used to using Google calendar for this. its a good app if you need a desktop version.
I've just deployed a few days ago, its a fair bit of techy work but it is working as it supposed to work.
Good luck...Dave