How to Deploy Windows 7 In The Enterprise

Windows 7 is coming to the enterprise at full speed. If you are like most companies, you skipped Vista at your business. Maybe it was installed on a handful of computers, mostly on test systems. Or, maybe, a plan was implemented to integrate new computers that came pre-installed with Windows Vista into the enterprise.

How to Deploy Windows 7 In The EnterpriseEither way, large scale rollouts of Windows Vista on the desktop were uncommon at most companies small and large. What that means, is that now you have to formulate a deployment strategy to rollout Windows 7 across your whole business.

What’s more, since it has been several years since you rolled out a new operating system across the enterprise, that knowledge and experience has faded. Not that it matters too much, considering how much it has changed — a fact acknowledged by Microsoft in their Windows 7 Deployment Frequently Asked Questions (it’s #1).

Whether you’ve been using automated deployment tools all along, or your last migration plan involved manually installing Ghost-ed images on multiple machines, it’s time to take another look at the deployment tools Microsoft has and the latest beta of its upcoming deployment package which will be customized to a Windows 7 rollout instead of a Windows Vista rollout.

Of course, you’ll want to grab Microsoft’s official Windows 7 pre-deployment checklist; but as with any document written for "everyone" there are a lot of things in there that might not be very useful to the average IT professional handling a company wide business rollout of Windows 7.

The short version of the pre-rollout checklist for Windows 7 deployments in most businesses goes something like this:

1. Figure Out Your Licensing

Yes, I hate it too, but unfortunately, in this world of piracy and ever changing business models, licensing has become a very real part of an IT professional’s job responsibilities. You don’t want to get rolling, only to get ambushed by a licensing issue, so nail it down now.

Do you have Software Assurance, or do you have a Volume Licensing agreement? Or are you still buying onesie-twosie? Do you have any upgrade rights? If so, is it worth chasing those down?

(Answer: Yes, if you have a lot and don’t have one of the business licensing agreements. No, if you only have a couple or your agreement covers you anyway. Why spend hours of frustration chasing down upgrade rights that will only save you a few bucks?)

2. Decide Which Version of Windows 7 To Deploy

This will primarily be driven by #1. The good news is that all the binaries for every version will be copied to the hard drive for every installation regardless of the original Windows 7 edition installed. The bad news, is turning on upgrades ad hoc is the start of a path to a licensing and management nightmare.

If you’re organization has the right structure and agreements in place, try to just standardize across the board on either Professional or Enterprise. (Go Enterprise if you can and the cost is similar. You’ll need those features eventually.)

3. Catalog Critical Applications

#1 on the list of why people hate Windows Vista is that it just didn’t work with lots of things that people counted on.

Make sure that doesn’t happen to your Windows 7 rollout by testing all of those applications that people complained about Vista breaking. If they don’t work, check out #4.

4. Test Applications in Windows XP Mode

One of the more brilliant moves Microsoft has made in the last few years was building a Windows XP mode into Windows 7. By now, if something isn’t compatible with Windows XP, it is considered a relic.

The premise of Windows XP Mode is that if your applications, printers, scanners, joysticks, or whatever, don’t work with Windows 7, then they should work in Windows XP Mode until they can be updated (or Windows fixed, whichever the case may be).

But, don’t trust your deployment to marketing hype and hope — test it.

5. Windows Server 2008 R2 Deployment

Two words: driver provisioning. Your Windows 7 deployment will go much faster and smoother when you take advantage of this new Server 2008 R2 feature of Windows Deployment Services.

Remember, there is no reason that all of your servers have to be upgraded to R2, just your deployment servers.

Of course, there will be several enterprise specific questions that will have to be answered, in addition to ensuring that your network and security models are all setup and ready for interaction with new Windows 7 clients coming online.

Check into the Microsoft Assessment and Planning Toolkit (MAP) for a detailed collection of tools and checklists.

The Windows AIK provides the tools necessary to build, maintain, and tweak (fix) your images throughout the deployment process. While standardization is a noble goal, do not get bogged down in fulfilling a corporate paradigm. Instead, focus on getting working, stable builds into the field.

Changing an image after installing 250 of 1,000 computers means that at the end of your Windows 7 deployment, you will have 750 problem-free installations and 250 non-standard installations. Contrast that with a 100% standardized installation but with 1,000 workstations now in need of updates and fixes.

You can start building reference systems and creating and testing images now, but before you get too far, be aware that you really need to be waiting for one more resource from Microsoft. The current Deployment Toolkit was designed around and for Windows Vista. While it can be used with Windows 7, a new version built specifically for Windows 7 rollouts is currently in beta.

The Microsoft Deployment Toolkit 2010 will be the one you want to be using for any large scale Windows 7 rollout.

Windows 7 Zero-Touch versus Lite-Touch Installations

Microsoft categorizes deployment strategies into basic rollout paradigms including two "high-touch" methodologies and a "lite-touch" and a "zero-touch" method.  While zero-touch sounds great in theory, in reality, it is more likely to be a "next OS" deployment strategy. 

For starters, it takes a whole other layer of server functionality called System Center Configuration Manager. If you are well into your deployment of SCCM, then obviously, it might be a viable option for your organization.

But, most organizations have done nothing more than tinker around with it, if anything at all. For those companies, trying to design, implement, troubleshoot, and stabilize a new technology is probably not the priority right before a major OS upgrade starts up. In that case, you’ll be confined to a "lite-touch" rollout, which is probably the way most IT departments will be comfortable with anyway.

The lite-touch paradigm is the one you have likely been slowly implementing over the years either with Microsoft’s latest tools, or with 3rd-party tools. With a lite-touch install, someone has to kick off the installation and take care of some basic customization and configuration at the beginning. Then, the automated systems take over and install and personalize the images resulting in a zero-touch from then on installation.

For all of a company’s locations that have professional IT staff on-site (or within easily travelable distance), this is probably how they will feel most comfortable doing the rollout anyway. As they say, no plan survives first contact with the enemy and there will undoubtedly be a bug or two to be fixed after at least a few installations — and there is no better way to handle that than with IT staff standing right next to the computer.

Despite the long and widely available beta and release candidate version of Windows 7 having matured from bleeding edge to RTM and soon full-release status, Microsoft’s latest OS is still brand-new, and brand-new software has a way of developing a quirk or two. No one is suggesting a full-speed ahead enterprise-wide development on the day Windows 7 is released, but a new corporate OS has been a long time coming.

A major migration like this is no easy task, and preparing now, is the way to ensure that your organization is ready when the "Go" call comes.

Windows 7 Deployment Training

Windows 7 Deployment Training

Learn more about deploying Windows 7 in the enterprise with Train Signal’s Windows 7 Deployment Training. The new course is currently the only video training course available on the market that covers Windows 7 deployment tools and techniques and includes everything you’ll need to master Windows 7 Deployment and prepare for the 70-681 MCTS exam.

Learn more about Windows 7 Deployment Training


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