I have an iPhone SE, up-to-date iOS. Suddenly stopped syncing calendar properly, as others have described. This started back in June. Contacts and email are fine.
I sync via cable to my computer, not through iCloud. Never knowing if all my calendar appointments have synced renders the who system unreliable! Now I have to look at both calendars to make sure everything is in place. It seems to be an Apple issue that they are unwilling to address. When I have talked to support, they always suggest contacting Microsoft. Microsoft says it's an Apple issue. These two should learn to play nice with each other!
I just fixed the same issue on one PC I was having a problem with. I have an iPhone7 and use Outlook and iCloud for Windows on my home and work PCs. My problem was with PC-Work. While PC-Home sent and received all iCal updates to and from my iPhone, PC-Work was unable to receive data, though it was able to send it. I tried to set iCloud Calendars, Contacts, and Reminders off and on, but this didn't help. So, to fix PC-Work, I manually removed all iCloud and '@me.com' data from Outlook (went to FileAccount settings Data Files). And, only then, I toggled iCloud Calendar Contacts, and Reminders on.
ICloud enables you to share calendar among your Apple products or with. In the Outlook Setup for iCloud window, choose one option according to your needs.
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