Configure the Exchange server to support Compatible mode by using the instructions from KB article 980436.This allows the Outlook for Mac client to establish a connection by using the SSL protocol and then renegotiate by using TLS. Learn about using Exchange (EWS) accounts in Mail with OS X v10.6 or later. Before you begin OS X Snow Leopard and later support Exchange Web Services (EWS) as a connection to your Exchange server. In the Outlook for Mac log collected for Outlook for Mac 2011 and Outlook 2016 for Mac through version 15.11.2, each entry has a name that identifies the feature that is being logged. The following table lists the label for each feature. Your suggestion is only valid for a mail client that uses ActiveSync. As I have already noted above Outlook for Mac does *not* use ActiveSync, it uses Microsoft's EWS. Oliver, please revisit & respond to my reply above.
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Microsoft Outlook for Mac Add Your Gmail Account to Outlook 2011 Mac Using IMAP. To set up your Outlook client to work with Gmail: Enable IMAP in Gmail. Spark for Mac helps cut down on the amount of time users spend managing email with a Smart Inbox, four configurable gestures in the message list, and Quick Replies for one-click responses in a flash. Paying for.mac (or some other IMAP) would give the same results as using AOL's free IMAP. The way around it, if I understand correctly, is to just take gmail out of the equation and use the IMAP email as my primary (only) email. Pine is an easy-to-use and rock-solid email client with great flexibility on Unix and with IMAP accounts for Windows, Mac, and Linux.
I doubt this a 'problem' with the mac as such nor does it have anything to do with Remote Desktop for Mac which is an entirely different product and for which this forum is for. Questions about RDC for Mac should be put on the relevant Microsoft forum rather than here. However your problem may be with your understanding of the secure remote connections requirements between your server and remote connections. I doubt you'd be aware of any of this as generally server administrators won't necessarily discuss them. By default a mac will not have server-client trust certificates installed simply because the exchange won't happen transparently between an MS based server and non MS-OS such as OS X.
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Starting in OS X El Capitan and iOS 9, people trying to set up a PPTP VPN connection on their iOS device or on their Mac would get a warning that looked like this:
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