Ryan
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One alternative is to subscribe to iCloud calendar with your Exchange/O365 email accounts or any Outlook account, and then sync the same accounts in Outlook for Mac. See details:
https://support.office.com/article/c9c67e41-274f-4527-ae5e-ea1003d89fc5
Ryan
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Howww is this not a thing yet. I have tried outlook for Mac since the beginning only to be disappointed by not having this feature amongst other things. I Started using the iOS outlook a little while back and that seems to have access to my contacts. This is outrageous, as every other email client under the sun has access to my iCloud contacts. Is outlook that messed up under the hood that it cant do this?!