Jira
Outlook Meetings for Jira is available for Jira Cloud and Jira Server 7 and higher.
It is currently optimized for Jira ServiceDesk, but it works the same way for Jira Software and Jira Business projects.
It is installed via the Atlassian Marketplace and does not require additional manual changes in JIra.
Microsoft Office
The addin only runs with Office 365 due to technical restrictions. It takes advantage of Microsoft Graph API.