As long as you can configure JIRA to access the Outlook 365 mailbox, it should work - http://office.microsoft.com/en-us/outlook-help/settings-for-pop-and-imap-access-for-office-365-for-business-or-microsoft-exchange-accounts-HA102908389.aspx
Yes, but if you use a fat client like Outlook 2013. The Outlook 365 web interface is not supported.
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