Settings: Settings are not accurately configured.
Cache Issue: Your Outlook Cache is corrupted. Failed to Connect: You failed to connect Outlook for Mac with the Exchange Server. Offline Mode: Your Outlook for Mac is in offline mode. Many users of Outlook for Mac face this issue, and so we need to realize the causes behind it. Prominent Reasons Behind this Synchronization Issue Due to this, mailboxes are not updated on the server-side and on the client-side, and it becomes necessary to fix Outlook for Mac not syncing with the Exchange Server. Sometimes, this synchronization process gets affected partially or fully. Synchronization between the server and client application is done so that whenever there is any modification in the Server-side or client-side, the change gets updated on the other side as well. It facilitates offline working in an Exchange environment. Outlook supports connecting directly to Smart Card Authentication by using a physical smart card or a TPM chip-embedded virtual smart card for each user.Ĭertificate-based authentication is supported for Outlook Web App (OWA) and Exchange ActiveSync clients, but not in Outlook that is running on Windows.Outlook for Mac provides Exchange connectivity in a Mac environment. Configure on-premises Exchange to use Hybrid Modern Authentication. Enable Modern Authentication in Office 365. For more information about how to enable Modern Authentication, see the following articles: 
To configure certificate authentication in Outlook 2016 and later versions, we recommend that you use Modern Authentication. Outlook uses the Windows Credential Manager to provide credentials to servers. This issue occurs because Outlook doesn't support using the Windows certificate store as a credential. This problem occurs especially if the network device is configured to require the client to present a certificate during the SSL handshake in the network layer instead of passing the traffic directly to the server that is running Exchange Server. The network device can be a load balancer or another network device, as described in Certificate Selection and Validation.
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