The Outlook Connector Version 18.104.22.1681 seems to support only SSL3 and TLSv1.0. If your Zimbra Server has disabled both, the Connector will not connect and throw errors like
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### ERROR ### WinHttpSendRequest(xxxxx.com:443) for 'AuthRequest' at 'UserSession::Auth#1746' returned ERROR_WINHTTP_CONNECTION_ERROR after 0ms. Client network adaptor down, or ZCS not running? SendRequestIntSynchronous#1654
I recorded the connecting attempts with Wireshark and saw only SSL3 and TLS1.0 Client Helos.
After re-enabling TLS1.0 with zmprov mcf zimbraReverseProxySSLProtocols TLSv1 the Outlook Connector worked as expected.
I haven’t found any informations about TLS1.2 support but I hope this will come soon because this is security related.
If you have more information on this topic, I would be glad to hear them