Connect to the Exchange Server using a Mac. When SSL is disabled and secure renegotiation is implemented as defined in RFC 5746, Outlook requires the server to be in Compatible mode so that the session can be renegotiated from SSL to Transport Layer Security (TLS). The connection failure occurs because Outlook for Mac uses SSL to establish communication with an Exchange server. Fix your Outlook email connection by repairing your profile Poor performance. 2459968 Outlook 2011 for Mac doesn't automatically set up your email server settings for Exchange Online in Office 365 Help articles. Cannot connect to Exchange Online by using Outlook.
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