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I got the iCloud calendar to sync to the new Outlook by creating an Apple app-specific password and adding a new email account from the new Outlook settings page. From the email accounts pane, select the option to add a new account
How to Add iCloud Email to Outlook 2016 YouTube Improved Productivity: With both calendars in sync, you'll have a birds-eye view of your schedule, making it easier to manage your time and prioritize tasks To the right of Calendars and Contacts, click , then turn on "Automatically sync your iCloud calendars and contacts to Microsoft Outlook." Click Done, then follow the onscreen instructions to set up Outlook. Because New Outlook does not support COM add-ins, you can't view iCloud calendar in New Outlook
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