You will need to export your Calendar to an ICS file:
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With Outlook 2013 or 2016 open, go to the Calendar you would like to export.
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Click File Save Calendar.
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This opens a window where you select to save the file to your computer, confirm the file name and click More Options.
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Change the date range so it includes all of the data you would like to export.
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Change the Detail to Full Details.
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Click OK and then Save the file.
Once you have exported the Calendar to an ICS file, you can import it into CARET Legal by following these instructions.
Exporting Outlook 365 Calendar to Excel
The steps above are compatible with Outlook 2013 and 2016.