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On these password prompts, you’ll notice it’s authenticating for the users e-mail address. However, when configuring external users, while you can eventually get it configured, the user is constantly prompted for credentials on every Outlook start. 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. Outlook 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. Now 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. 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.