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Can I send a calendar event to two different people at two different times? For example, once the event is created in the calendar, I would like an email notification to one person, on the day of the event, I would like it to go to another person? Is that possible?

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To answer your question: OOTB -> No. Workflow -> Yes.

The workflow can start on item-creation, send the mail to the first person, will be set on-hold-until-date (or for X weeks/days/hours) and send the mail to the second person. You can check this link (docs.microsoft.com) for further information.

Within this documentation you will get a direction on how to create workflows with SharePoint Designer.

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