Managing Macs using System Center Configuration Manager – Part Two

In my previous article, I described the agent that Microsoft have put into System Center Configuration Manager to manage Macs with. Overall, while I was happy to have some kind of management facility for our Macs I found it to be somewhat inadequate for our needs and I wished it was better. I also mentioned that Parallels, the company behind the famous Parallels Desktop virtualisation package for the Mac, contacted us and invited us to try out their plugin for the Mac. This article will explain what the Parallels agent is capable of and how well it works and how stable it’s proven to be since we’ve had it installed.

Parallels Mac Management Agent for ConfigMgr

The Parallels agent (PMA) is an ISV proxy for ConfigMgr. It acts as a bridge between your Macs and the management point in your ConfigMgr infrastructure. The agent doesn’t need HTTPS to be enabled on your ConfigMgr infrastructure, ConfigMgr sees Macs as full clients. The Parallels agent fills in a lot of the gaps which the native Microsoft agent has such as:

  1. A graphical and scriptable installer for the agent
  2. A Software Center-like application which lists available and installed software. Users can also elect to install published software if desired.
  3. Support for optional and required software installations
  4. Operating System Deployment
  5. The ability to deploy .mobileconfig files through DCM
  6. A VNC client launchable through the ConfigMgr console so you can control your Macs remotely
  7. Auto-enrollment of Macs in your enterprise
  8. Support for FileVault and storage of FileVault keys

It supports almost everything else that the native ConfigMgr client does and it doesn’t require HTTPS to be turned on across your infrastructure. In addition, if you use Parallels Desktop for Mac Enterprise Edition, you can use the plugin to manage VMs.


The PMA requires a Windows server to run on. In theory, you can have the PMA installed on the server hosting your MP or it can live on a separate server. There are separate versions of the PMA available for ConfigMgr 2007 and 2012/2012 SP1/2012 R2.

Earlier versions of the PMA didn’t support HTTPS infrastructures properly so you needed to have at least one MP and one DP running in HTTP mode. However, the latest version supports HTTPS across the board. However, you do need to have at least one DP running in anonymous mode for the Macs to download from.

IIS needs to be installed on the server along with WebDAV and BITS. Full and concise instructions are included so I won’t go over the process here. Anybody who has installed a ConfigMgr infrastructure will find it easy enough.

If you are using the OSD component, it needs to be installed on a server with a PXE enabled DP. If you have multiple subnets and/or VLANs, you will need an IP helper pointing at the server for the Macs to find it.

Software Deployment

The PMA supports two methods of deploying software. You can use either Packages or Applications.

Generally speaking, there are three ways to install a piece of software on a Mac, not counting the App Store:

  1. You can have an archive file (Usually DMG) with a .app bundle in to be copied to your /Applications or ~/Applications folder
  2. You can have an archive file with a PKG or MPKG installer to install your application
  3. You can install from a PKG or MPKG.

Installing using Packages

Unlike the Microsoft agent, you don’t need to repackage your software to deploy it with the PMA. To avoid doing so, you can deploy them using legacy style Packages. To deploy a piece of software using ConfigMgr Packages, you need to create a Package in the same way as you would for Windows software. You copy it to a Windows file share. You need to create a Program inside the package with a command line to install the package. Using the three above scenarios, the command lines would look like this:

  1. :Firefox 19.0.2.dmg/
  2. :iTunes11.0.2.dmg/Install iTunes.pkg::
  3. install.pkg

The first command tells the PMA to open the DMG and copies the bundle in the DMG to the /Applications folder. The second tells the PMA to open the DMG and execute the .pkg file with a switch to install it silently. The third runs an arbitrary command.

Once the package and the program inside the package have been created, you distribute to a DP and deploy it to a collection as standard.

Deploying software using this method is functional and it works nicely. The disadvantage is that there is no way to tell if a deployment has worked without either delving through the logs or looking in the Applications folder. If you deploy the Package to a collection, the PMA will try to install the Package on the Mac whether it’s already on there or not.

Installing using Applications

As of version 3.0 of the PMA, Parallels have started supporting ConfigMgr Applications as well as Packages. Parallels are using Microsoft’s cmmac file format to achieve this. This means that you need to repackage applications and add them to the ConfigMgr console using the same method as you do for the native ConfigMgr client. This is a bit of a pain but the benefits that doing so brings make it worthwhile. As with the Microsoft client, there are detection rules built into the Application meaning that the Parallels client can check to see if a piece of software is deployed on the Mac before it attempts to deploy it. If it is already there, it gets marked as installed and skips the installation.

It also brings this to the table:


That is the Parallels Application Portal. Much like Software Center on Windows, this gives you a list of software that has been allocated to the Mac. It allows for optional and required installations. If a deployment is marked as optional, the software is listed with a nice Install button next to it.

As with the Microsoft agent, you need to be careful with the detection rules that you put into your Applications. The PMA runs a scan of /Applications and /Library folders looking for info.plist files. It extracts the application name and version from those PLISTs and adds them to an index. It then looks at the detection rules in the Application and compares them to the index that it builds. If there’s a match, it marks them as installed. If you don’t get the detection rules right, the PMA won’t detect the application even if it has been installed properly and then it eventually tries to reinstall it. I spent a very interesting afternoon chasing that one down. There are also some applications which don’t have info.plist files or get installed in strange places. The latest Java update doesn’t have an info.plist, it has an alias to another PLIST file called info.plist instead. The PMA didn’t pick that one up.

Operating System Deployment

Quite impressively, Parallels have managed to get an operating system deployment facility built into the PMA. It’s basic but it works.

First of all, you need to create an base image for your Macs and take a snapshot of it using the System Image Utility found in OS X at /System/Library/CoreServices/. You can create custom workflows in this utility to help you blank the hard disk before deployment and to automate the process. Make sure you tell it to make a NetRestore image, not a NetBoot image like I first did. Once you’ve done that, you tell it where you want to save your image and set it on its way. The end result is an NBI file which is a bundle with your system image and a bootstrap.

You then copy the resulting NBI file onto a PC or server with the ConfigMgr console and Parallels console addon installed. Once it’s on there, open the console and go to the Software Library workspace. Go to Operating Systems, right click on Operating System Images and choose Add Mac OS X Operating System Image. A wizard appears which asks you to point at the NBI file you generated and then to a network share where it creates a WIM file for ConfigMgr.

add image

Once the WIM has been generated, it adds itself to the console but one quirk I have noticed is that if you try to create it in a folder, it doesn’t go in there. It gets placed in the root instead. You can move it manually afterwards so it’s not a huge issue.

The next step is to create a task sequence. There is a custom wizard to this too, you need to right click on Task Sequences under Operating System Deployment in the Software Library workspace then choose Create Task Sequence for Macs.

task sequence

You give the task sequence a name, choose the image that you want to use and press the Finish button. Again, if you’re using folders to organise your task sequences and you try to create the task sequence in a folder, it will get placed in the root of the structure rather than in the folder that you tried to create it in. You can move it if you wish.

From there, it’s pretty much standard ConfigMgr. You need to distribute the image to a DP and publish the task sequence to a collection. The task sequence then appears to the Macs in that collection as a standard Netboot image with the title that you gave to it. You can access it the usual way, either through the Startup Disk pane in System Preferences or by holding down the option key on startup.

boot disk

Unfortunately, what it doesn’t do is allow for any kind of automatic, post image deployment sequences. Although in theory the System Image Utility is supposed to support custom workflows which allow software installations and the running of scripts, I haven’t managed to get it to deploy the agent automatically. I have therefore created a script which the admin deploying the Mac needs to run which (amongst other things) names the Mac and installs the PMA. From what Parallels tell me, this is being worked on.

DCM – Scripts and Profiles

The PMA supports the usage of DCM Bash scripts in the same way as the Microsoft agent does. There isn’t much to say about this, it works and it’s a useful thing to have. The other way of getting settings onto Macs with the PMA is via mobileconfig files generated either by Profile Manager in OS X Server or by a generator built into the ConfigMgr console addin. The generator looks like this:


Look familiar? Unfortunately there aren’t all of the options here that are in Profile Manager so if you want to do something more advanced than what’s on offer here, you still need a copy of OS X Server and Profile Manager to generate the profile.

To deploy a mobileconfig file using the PMA, you need to go to the Assets and Compliance workspace, go to Compliance Settings and right click on Configuration Items. Go to Create Parallels Configuration Item then to Mac OS X Configuration Profile.


You then give the configuration item a name, decide whether it’s a User or System profile and point the wizard at the mobileconfig file generated by Profile Manager. Once you’ve done that, there is a new configuration item in your console which can be added to a DCM baseline and deployed to a collection.

I have used this facility for various purposes; for configuring Airport, for joining the Mac to the AD domain, for setting up the user’s desktop settings and wallpaper, setting up Time Machine and for more besides. It’s a great facility to have and rather more user friendly than delving through PLISTS to find settings.

Other features – VNC Client, Auto-enrolment and  Inventory

Well, these do what they say on the tin. We have a VNC client:


It takes an inventory:

mac inventory

It has the ability to detect Macs on your network and automatically install the agent on them. They all work. There isn’t really much else to be said.

How well does it work?

So clearly, the PMA has far more features than the Microsoft agent does but a piece of software can have all the features in the world and still be useless if it isn’t stable. In this regard, I am delighted to say that the Parallels agent has been rock solid for us. It has been continually improved and has had feature after feature added. It doesn’t quite make a Mac a first class citizen on a Windows network but it comes very close and going by the way that Parallels have improved the product over the last two years, I’m confident that the gap will close. Parallels have been a lot quicker in getting new versions of OS X supported with their plugin too, it already has support for Yosemite.

It hasn’t been entirely problem free but when I’ve contacted Parallels Support, they’ve been quick and efficient and they’ve got the problem resolved. Most problems that I’ve come across I’ve managed to solve myself with a bit of thought.

Although Parallels claim that it the PMA can be installed on the same server as your management point, I couldn’t get it to work when I did this. I ended up putting it on its own hardware. This was with v1.0 of the product though, we’re now on v3.1 so they may have improved that since then.

Having the PMA has also meant that I no longer need a Magic Triangle set up to support and configure my OS X clients. I don’t need Profile Manager or Workgroup Manger to deploy settings, I don’t need OS X server or DeployStudio to deploy images. The only thing I need OS X Server for is Profile Manager to generate the profiles and (with the arrival of Yosemite) the System Image Utility.

The only real downside to the PMA is that it’s expensive and that you have to pay full price for it annually. That may be hard to justify if you’ve already spent a fortune on a System Center license.


So lets do a quick advantage/disadvantage comparison:

Microsoft client advantages:

  • Native client so no additional cost
  • Support from Microsoft

Microsoft client disadvantages:

  • Sparse feature set
  • Required installs only
  • Complicated DCM
  • Takes a long time to install multiple applications
  • Requires HTTPS
  • Slow to support new versions of OS X
  • No visible status indicators, next to impossible to see what’s going on.

Parallels client advantages

  • Includes lots of additional features, brings level of management of Macs to near parity of Windows machines
  • Optional and user initiated installs supported
  • Software Center equivalent and a System Preferences pane to check status of agent. Very thorough logs to check on what the agent is doing are available too.
  • OSD
  • Doesn’t require HTTPS
  • Supports SCCM 2007
  • Much easier to deploy settings by using mobileconfig files

Parallels client disadvantages

  • Expensive
  • Requires an additional DP
  • Probably requires an additional server to install the proxy

They’re as good as each other when it comes to running DCM scripts and taking inventories. So the answer is simple: If you can afford it, get the Parallels Management Agent. If I were the head of the System Center division at Microsoft, I’d be going cap in hand to Satya Nadella and telling him to drive all the money to Parallels HQ to acquire their product from them. Frankly, it puts Microsoft’s own efforts to shame.

1 comment on “Managing Macs using System Center Configuration Manager – Part Two”

  1. Pingback: Configuring a Mac Image Using Microsoft SCCM & Parallels Mac Management

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