Connecting Apple Macs to Windows Server 2016 Essentials

In the last part of the guide, we added Windows PCs to our Windows Server 2016 Essentials network – but they’re not the only type of computer that can access our new server.

Small business and prosumer environments are becoming ever more complex with multiple devices and operating systems in use. In the past, life was a little easier as most devices would be running some kind of edition of Windows but in the last five years, the world has seen a shift.

We’re still using Windows PCs, of course, but they’ve been joined by Apple Mac desktops and notebooks, iOS and Android mobile devices, a growing number of Windows mobile devices and computers running Linux.

Even on the Windows PC side, not all versions of Windows are created equal. As we saw in the last chapter, Home editions of Windows cannot be joined to a Windows Server domain. If you’re confused about what devices will work well with Windows Server 2016 Essentials and what won’t, then I hope this book will help answer your questions. In this chapter, we’ll walk through connecting some of the more popular alternative computer operating systems to the server (that unfortunately aren’t able to use the full Essentials feature set like the Windows Enterprise and Pro PCs we connected in the last chapter. In the next chapter, we’ll switch to mobile devices.

This walkthrough is part of our 625 page guide to Windows Server 2016 Essentials. Pick up a copy today!

Connecting Apple Macs to the Windows Server Network

Windows Server 2016 Essentials officially supports the connection of Apple Macs running the following operating systems:

  • Mac OS X v10.5 Leopard
  • Mac OS X v10.6 Snow Leopard
  • Mac OS X v10.7 Lion
  • Mac OS X v10.8 Mountain Lion
  • Mac OS X v10.9 Mavericks
  • Mac OS X v10.10 Yosemite
  • Mac OS X v10.11 El Capitan

Windows Server 2016 Essentials does not currently support the latest edition of MacOS – v10.12 Sierra. You will be blocked from installing the Windows Server Essentials Connector on this release. I anticipate that this situation will change – but Microsoft has not provided timing for Sierra support at this point. If your Macs are running MacOS Sierra, go ahead and follow the instructions below – you never know when support will be available!

Once connected to the network, you can view the health and backup status for a Mac computer from the Windows Server 2016 Essentials Dashboard. However, you cannot configure computer backup or start a backup from the Dashboard. Nor can you use Remote Web Access to connect a Mac computer to the network (as you can with a Windows PC).

Installing the Windows Server Essentials Connector on a Mac does require a bit of ingenuity. You may not initially be able to access the server using the server name to download and run the connector from your web browser. If this occurs, try swapping the server name for its IP address in the address bar (so http://myserver/connect becomes If that fails, you can get the process started by download the Mac Connector software on a Windows PC using the Download software for Mac link and copy it over to the Mac.


Opening the .dmg file allows you to install the Connector software. When you open the .dmg file, you can double click the Connector for Mac app to start your installation.


You are asked for your Mac administrator password to proceed, following which this installation wizard begins.


You are then led through a series of wizard screens to install the connector on the Mac. Click Continue. We start by being asked to enter the name of your Essentials server.


If you receive a message stating that your server cannot be found, then try again but use the server’s IP address rather than its name. That usually does the trick. Next up, type in an identifier for your Mac (paying attention to the naming rules mandated – 15 characters or less, no names that are numbers only, no spaces or special characters) and then Continue.


Now you’ll be asked to type in your network user name and password – at this point, enter your Essentials Server administrator details and click Continue.


Next, you need to enter a description for the computer, then click Continue. This description will be visible in the Windows Server Dashboard as well as your Remote Web Access site.


The installation proceeds and in no time at all, you’ll be connected to the server.


You can choose whether or not to have the Windows Server Launchpad open when your Mac boots up. The Launchpad is a small application that allows you to connect to a subset of features available on the Windows Server Essentials Dashboard.

Click Close to finish the installation wizard, and the Windows Server Launchpad will open.


Enter a network user name and password (with administrator privileges) to connect to the server. The Options dropdown menu will allow you to select a setting to remember your account credentials.


Note that there is there is no Dashboard option in the Mac Launchpad. The simple fact is that a Mac cannot connect to the Essentials server through the Dashboard. Any Dashboard administration you need to do will need to be performed on a Windows PC, directly on the server itself, or via a Remote Desktop Connection. The Microsoft Remote Desktop app, available from the Mac app store, provides much of the functionality you’ll find in Windows’ own Remote Desktop feature.


Let’s take a quick look at the Dashboard now. You can see, the number of devices on my Essentials network is beginning to grow.


Double click on your Mac in the Dashboard’s Devices tab to view its properties.


Accessing Windows Server 2016 Essentials Files and Folder With Finder

Of course, with your Mac and server located on the same network, you should be able to see and access your server files and folders in Finder on the Mac. Use the Connect As… button to enter your server account credentials.


With a standard user account, you’ll see that server access restrictions are maintained in the Mac – I’ve logged in with my account (TerryWalsh) and you can see everyone else’s account is blocked for me (note the “no entry” icons).


For you, this task may only have just begun. You have some work to do, so take your time and finish up adding your remaining computers to the Windows Server 2016 Essentials domain.



  1. For the incompatibility with 10.12 Sierra, if you right click and select “Show Package Contents” on the “Connector for Mac” and then browse to Contents/MacOS and run the “Connector for Mac” you will see a terminal output as the connector tries to run. The issue you will see is “Objective-C garbage collection is not supported”. This is an issue that is affecting many other older mac applications such as “Gitx” There was an article 2 years back stating that applications that use this garbage collection will have to migrate to ARC. The MAC connector bundled with Server Essentials 2016 shows a date of 2014 so it looks like Microsoft will have to rewrite some code to take out the Objective-C garbage collection if this will ever work with Sierra. Fingers crossed.

  2. Is there a way to set up a Mac (OS X 10.10.5) with the automated backup in WSE 2016?
    In the Dashboard it shows as “Not set up” and i cannot configure it. All Windows Clients are using the backup and it would be sweet if the Mac could be backed up the same way.

    1. I never found a way to set up backing up of a Mac with WSE. All it does is open TimeMachine pointing you to sue that. I have read there is some complicated way to point TimeMachine to a fake drive hosted on the WSE storage but it’s just easier to get a flash / external drive, keep that plugged into the mac, and backup to that.

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