Work Time Tracking Calendar for Jira v 5.4.x: Export to Outlook

First, you will need to create an export for the desired calendar as described in Work Time Tracking Calendar for Jira v 5.4.x: Exports Create and Edit.

Once the calendar export is created, copy the generated URL from the iCalendar URL column.

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Open the Outlook calendar. On the Home tab, click on the Open Calendar button. 

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In a dialog, insert the copied generated link:

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The events from the Work Time Calendar will be shown on your Outlook calendar. 

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