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I have created multiple calendars for different departments and use overlays to display everything in a single Master calendar.

For some reason, none of the overlayed dates show up in Outlook when I connect it. Outlook will only show the blank Master calendar.

Any ideas? Thank you!

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Correct, Outlook connects to the calendar instance you're connecting to. You'll need to connect to each calendar individually and then you can overlay within Outlook.

HTH

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Pretty crazy that even today, with SharePoint Online, this is still the case. – idon'twearsuits Nov 20 '15 at 23:07

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