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The Mac Consultant's Guide To Managing Windows Product Keys

Volume Number: 23 (2007)
Issue Number: 09
Column Tag: Macs and Windows

The Mac Consultant's Guide To Managing Windows Product Keys

Do your customers (and yourself) a favor with our best practices

by Joe Froehlich

It's all in your mind

In spite of an ever increasing need to live, work, and play in a cross platform environment, the rift between PC and Mac users often appears to be widening rather than narrowing. Mac users cherish the simplicity of the Mac while PC users seem to almost relish complexity. After all, if a computer isn't difficult to use and maintain, it can't possibly be a serious business tool, right?

Having switched primary platforms several times over the course of my career, I've learned one important lesson–people don't like change, especially when it threatens their comfort zone. To survive a change successfully, you need to "adjust" your mindset. Typically, this means learning (and ultimately accepting) new and different ways of approaching things.

Sleeping with the enemy

With the advent of virtualization products such as Parallels Desktop and VMware Fusion, consultants and support professionals alike are facing new challenges. The key to turning these challenges into opportunities lies in learning how to respond appropriately to client requirements (without saying "Ugh, it's Windows" to yourself). In this article, I'll provide some best practices for getting started with supporting Mac users who want to run Windows, regardless of whether it's on a physical or a virtual machine.

Get with the program

One of the best ways to bring yourself up to speed on Windows-related technology is to get your hands on the actual operating systems and applications you'll be supporting. Fortunately, Microsoft provides two specific programs that you should consider joining, depending on your objective.

Figure 1: Microsoft Partner Program at

Microsoft Partner Program

The Microsoft Partner Program, shown in Figure 1, consists of three distinct membership levels:

* Registered

* Certified

* Gold Certified

The Registered level is free (after a one-time registration process) and best-suited for people who support clients in single-office home-office (SOHO) or small and medium-sized business (SMB) environments. The Certified and Gold Certified levels require a substantial annual fee and proof of certain technical and business competencies. You can find a comparative summary of program benefits at

Once you sign up for the Registered Microsoft Partner Program, you're eligible to purchase the Microsoft Action Pack Subscription. This subscription includes quarterly mailings that provide technical and business resources appropriate for consultants and value-added resellers (VARs). It also includes a comprehensive collection of Not-For-Resale (NFR) software for the major Microsoft operating systems and applications. While licensing varies somewhat across titles, in general, you'll receive license keys that allow 10 client activations and 1 server activation per title.

Microsoft TechNet

Figure 2: Microsoft TechNet at

Whereas the Microsoft Partner Program is designed for consultants and VARs, the Microsoft TechNet program, shown in Figure 2, is geared more toward technical support professionals in enterprise environments. There are simply too many program benefits to describe fully in this article, but they include items such as planning and deployment tools, complimentary professional support incidents, managed newsgroups, virtual labs, and e-learning courses. And finally, TechNet subscribers receive a free subscription to TechNet Magazine, a hands-on monthly publication containing articles written by Microsoft's engineering team.

Arguably, one of the most compelling benefits Microsoft TechNet offers is access to full-version commercial products (without time limits or feature limits), including all Windows operating systems, all application software, and all server products. Again, licensing varies somewhat across titles, but most license keys are valid for 10 activations.

TechNet subscriptions are available under three different distribution schemes:

* Direct (download only)

* Single User (single workstation install)

* Server User (single server install)

For a detailed comparison of these subscriptions, point your web browser to

You have the tools, now what?

Aside from the value of the business and technical information you receive as part of the Partner and the TechNet programs, your real learning starts with installing and configuring the software you acquire through these programs. Before you launch your first Setup Utility, however, you need to think about how you're going to manage your license keys. While 10 activations may seem like a lot at first, you can easily expend them, especially if you need to do frequent re-installations or configure the software differently for specific projects.

For example, as a technical documentation developer, I often need to set up different software environments so I can take screen captures describing the tasks I'm writing about. Similarly, as a consultant or support professional, you may need to set up environments that mimic those of your clients. Or, you may simply need to test applications running in unique operating system environments. In any event, the point of thinking about license activation in advance is to make sure you use your license keys wisely without activating them unnecessarily.

Remember my introductory comments about mindsets? You're working with Windows here not Mac OS X–you can't just nuke and repave at will (at least not without requesting a reactivation key from the mothership). In the upcoming sections, I'll provide some best practices that have worked well for me over the years. I believe they'll serve you well, too.

We're going virtual, baby!

Thanks to virtualization software, you can install and configure operating systems and applications to your heart's content–all without needlessly wasting licenses. However, when you create a virtual machine, don't think of it as the machine you'll use for everyday tasks. Instead, think of it as a master (a pristine configuration) that you can clone for specific tasks as needed. The guidelines presented next work well for client installations you support as well as project-based scenarios.

Create the virtual machine manually

Whenever possible, avoid using the installation assistants that VMware Fusion and Parallels Desktop offer. Instead, create the machine manually, as doing so gives you more control over its initial configuration.

Tweak the virtual hardware

Before booting the virtual machine, edit its configuration to tweak the virtual hardware as desired. For example, I like to point the virtual CD/DVD to an ISO image of the installation media, as shown in Figure 3. I usually keep that image in the same folder as the virtual machine. This way, I don't have to go looking for the CD/DVD if I need to install additional operating system components.

Figure 3: The Configuration Editor in Parallels Desktop

Perform a basic installation

Boot from the installation media (physical disc or ISO image) and follow the Setup Utility's prompts to complete a basic installation. In doing so, however, avoid as much customization as possible. You'll want to customize the clones (later) not the master machine.

Install critical updates

After the Windows operating system is installed and the virtual machine boots from it the first time, run Windows Update services to download and install only critical updates. Always reserve recommended updates for clones of the virtual machine.

Scrutinize your work

Take a break and ask yourself if the virtual machine is in a state that you want to use as the basis for cloning? Depending on the software title and its license, you have either 30 or 60 days to activate it. Depending on the project you're working on, you may not need to activate the license key at all because it's a short-term scenario.

Activate the product

Your master virtual machine isn't ready for cloning until you complete the Windows Genuine Advantage verification. However, you can't do that until after you've activated the product. So, when you're ready to proceed (you're certain, right?), activate the product, run Windows Update again, and complete the Windows Genuine Advantage verification process.

Back it up, then clone it

At this point, restart the virtual machine one last time (to make sure it starts up without problems), and then shut it down completely. Now, back up the entire folder containing the virtual machine (minus the installation ISO if you have one in the same folder). Then, to clone the machine, simply duplicate its folder. Before launching the clone, however, you may need to modify your virtualization application's preferences so it knows you want to work with the clone rather than the master.

Just one more thing

I generally like to create at least two virtual machine masters: one with just the base operating system, and one with the operating system plus my primary applications (MS Office, for example). I first activate the operating system, as described above. I then clone the virtual machine and install my applications. I activate the applications, and then clone the virtual machine a second time. This technique allows me to revert to a clean installation of just the operating system, or the operating system plus my applications.

Let's get physical

You can use a similar process to protect your licenses on physical machines, including those hosting Apple's Boot Camp. Of course, you'll need a different toolset for that task.

To clone a physical installation, you need to be able to image the PC's boot drive–both the boot sector and the primary boot partition. One of the tools I've found useful for this job is Acronis True Image Home, shown in Figure 4. This product allows you to create a bootable CD/DVD that contains both hard disk and network drivers so you can generate a full image backup of the boot drive, store the image on the appropriate backup device, and restore it when needed.

Figure 4: Acronis True Image Home

In this scenario, you can take the same general approach described earlier, i.e. do a clean installation without any customization, install critical updates, activate the operating system, and go through the Windows Genuine Advantage verification. Next, install Acronis True Image Home, create your boot rescue media, and then image the boot drive. If you need to reinstall the operating system, simply boot the machine from the rescue media, and then restore the image.


Having a practical method for protecting Windows license keys make sense for both you and your clients. While we focused on you in this article, there's no reason you can't implement the same practices at client sites. After all, they need to protect their keys as well.

Joe has extensive experience in the IT industry, serving as a technical trainer and instructional designer as well as personally authoring several IT certification titles. He's a member of the Microsoft Partner Program, the Apple Consultants Network, the IEEE Computer Society and holds several industry certifications (A+, Network+, i-Net+, Security+, CNA, MCP, ACHDS, ACTC). You can reach him at


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