Company Calendar Planner for Jira v 5.6.x: Calendar export to Outlook

First, you will need to create an export for the desired calendar as described in Creating and editing a calendar export.

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

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

In a dialog, insert the copied generated link:

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