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Internally on the LAN, Outlook 2016 clients have absolutely no issues, and authentication is working fine (no password prompts). ![]() Internally inside of the LAN this is all automatic if you configured Exchange properly, but you will have to configure autodiscover externally. This means that you HAVE to have autodiscover setup, and working fluidly. They do this for “reliability” and ease of configuration. #Mac mail exchange 2013 manualOutlook 2016 does not allow manual or custom configuration of Exchange accounts. Right off the bat, everything is working fine, Outlook 2010 is working great, Outlook 2013 is working great. #Mac mail exchange 2013 windowsNow let’s flash forward to this migration from SBS 2008, to Windows Server 2012 R2 with Essentials Experience, and throw Exchange 2013 in to the mix. I always liked this as it provided some protection if the users password ever got compromised (in a phishing attack, fake e-mail logon page, etc…), as the password could not actually authenticate when using the e-mail address as a username (the username was never actually provided in the attack, only e-mail). Also, our buddy John Doe would have a AD UPN (this was automatically populated on user setup) An example would be “John Doe”, with the username of “JohnD”, and the e-mail address of “ ”. Now if you’re like me, another thing I always configured, was user accounts that didn’t match e-mail addresses. ![]() guys, except for a few configuration considerations when setting up Outlook clients, DNS, etc… This has never really posed any problems for us I.T. This used to be considered best practice, and most of us even configured. I wanted to open a discussion on a big issue I had a couple years ago in one of my first migrations from SBS 2008, to Windows Server 2012 R2 with the Essentials Experience role installed, with Exchange Server 2013.Īs most of you know, SBS comes packaged to push “.local” domains on initial domain configuration. However, some of these old environments are starting to catch up with us. ![]() More Informationįor more information about SSL/TLS Renegotiation, please review this TechNet blog post.There’s quite a few of us that started off deploying Small Business Server (SBS2008, SBS2011) environments back in the day, loving the handy all-in-one package taking care of everything from Active Directory and Exchange, to disaster recovery and business continuity. #Mac mail exchange 2013 for macNoteDo not configure the server to use Strict mode, as this prevents the Outlook for Mac client from connecting to the Exchange server. External connections to Exchange Server may be blocked if this server is in Strict mode. If you are using a security product such as Microsoft Forefront Threat Management Gateway (TMG) for managing connections to Exchange Server from outside your company, you will need to configure your TMG server using KB article 980436. This method allows Outlook for Mac to connect to the server even when SSL 2.0 and 3.0 are blocked. This allows the Outlook for Mac client to establish a connection by using the SSL protocol and then renegotiate by using TLS. WorkaroundĬonfigure the Exchange server to support Compatible mode by using the instructions from KB article 980436. 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. You cannot connect to a server that is running Microsoft Exchange Server from a Microsoft Outlook 2016 for Mac or Outlook for Mac 2011 client after disabling Secure Sockets Layer (SSL) on the server. Outlook 2016 for Mac Outlook for Mac for Office 365 More. ![]()
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