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Hello GerbrichA, please try to install Parallels tools manually and let us know if that makes any changes.Since updated (OS Sierra & Parallels 12) I do have Problems with sync my Outlook2007+outlook connector (running under W10) with my Outlook.com calendar and mail. Contacts are sync.
Sorry for my english - I am from Austria
Try to change the network mode to Bridge(Default Adapter) and let us know if that makes any changes.I did! I reinstalled and/or repaired Outlook, Outlook-Connector, the account (...@outlook.com) with and without rebbotinng between the single steps. ...
Any other idea?