Synchronising calendar items is a whole different problem, where you will need to select each and every calendar item individually, or at least change the view to Month and select entries month by month, and copy them to Exchange Online. This is far from ideal, but it works, even if it does take some time. Once you have all the email and contact items imported, which will create an On My Computer folder, select all the email or contact entries from your old Outlook and then drag them to the new Exchange Online account in Office 365. Alternatively you can select the import Outlook 2011 data on the computer in the Import dialogue of Outlook 2016 for Mac. Synchronising email and contacts is relatively straightforward with the fall back option being to export from Outlook 2011 for Mac and import to Outlook 2016 for Mac. Outlook for Mac will only export an OLM file, which can’t be transported to Azure in order to use the data import tool in Office 365, as that only supports PST files.
If you’re an Apple Macintosh user and you want to migrate and synchronise your Outlook 2011 for Mac or Outlook 2016 for Mac data to Office 365 Exchange Online it’s not all that easy.
