Each time an issue is scheduled it appears in the iCAL calendar and if I want to see that in my outlook calendar I need to export and save it each time.
https://confluence.atlassian.com/display/TEAMCAL/Subscribing+to+Team+Calendars+from+Microsoft+Outlook
I am looking for JIRA issue calendar macro but not for TEAMCAL
AFAIK there is not a way currently, but there is talk that there might be:
https://answers.atlassian.com/questions/222512/how-to-jira-calendar-plugin-or-simple-calendar-plugin-in-microsoft-outlook
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