Is there a reason to move to Windows 8 in the enterprise? Maybe a few, but probably not enough...

I've been all over the US this year speaking about desktop virtualization and the future of Windows, and part of that discussion is what, if anything, should people do with Windows 8.

I've been all over the US this year speaking about desktop virtualization and the future of Windows, and part of that discussion is what, if anything, should people do with Windows 8. I maintain now, as I did before the launch, that Windows 8 should be placed on the back burner when it comes to priorities in the IT department, and that the primary focus today should still be on getting to Windows 7 across the board and compartmentalizing your users and applications as much as possible (all off which leads to better desktop management). That said, there are a few people that see Windows 8 as a strategic platform for niche use cases around their organizations, mostly some sort of mobile use case where Surface Pro tablets will offer some needed flexibility.

Still, what if you were 100% migrated to Windows 7, and what if you were 100% committed to Microsoft going forward? In that case, is there a reason today to shift to Windows 8 in the enterprise? Let's look at some of the aspects that should factor in to the decision. To be clear up front, this is not looking at WinRT, which is the version of Windows that runs on ARM-based machines and the current Surface tablet. WinRT-based machines are effectively unmanageable, at least by the same methods we use to manage our regular Windows desktops. They are essentially like any other mobile device, so managing them requires more of an MDM/MAM approach.


Licensing belongs in the "low-hanging fruit" category of reasons to upgrade to Windows 8. With it's release, Microsoft has also somewhat simplified the licensing for the OS, especially in VDI environments. Essentially, you must have SA to do anything useful. You'll need SA on a primary computer before you purchase a Companion Device License, for instance, or Windows To Go. It's Microsoft's way of locking you in, and while it may be easier to decipher what's needed to license Windows in your environment, it's not exactly the kind of changes the community was looking for. For more information on this, check out Brian's post from April: Microsoft announces virtual desktop licensing changes for Windows 8. Guess what? They're still screwing us! 

Nonetheless, with fewer editions of Windows and a clearly defined licensing model, there is sort of implied benefit of moving to Windows 8 as long as you have SA.

Traditional PCs

The elephant in the room when talking about replacing Windows 7 (or XP, for that matter) with Windows 8 is the interface changes, and you'd be hard pressed to find someone that completely adores all the changes. If you do, that person is probably a IT person or general geek that likes anything new. I like new things. I like the way Metro looks (although we've been calling it TileWorld for a while now because "Windows 8 Interface" is weird). I even kind of like the way the Surface tablet that we bought for testing feels. In no way does that mean that I want to use Windows 8 in the enterprise, though.

Paul Allen wrote a blog post (yeah, that Paul Allen) with his review of Windows 8, and even he found it frustrating that there are different version of applications in Metro TileWorld vs the desktop, and that those applications aren't aware of each other. His words are much more carefully chosen than mine, and probably do a better job of explaining the problem:

"I did encounter some puzzling aspects of Windows 8. The bimodal user experience can introduce confusion, especially when two versions of the same application – such as Internet Explorer – can be opened and run simultaneously. Files can also be opened in either of the two available modes. For example, after opening a PDF attachment in Outlook from the desktop, Windows opens the file in Microsoft Reader, an application more suited for use on a tablet, rather than the desktop Acrobat Reader. A manual switch is then required to return to desktop mode. Thankfully, you can alleviate these switching problems by changing file and program associations in Windows, as I'll explain later."

I would've said something like "…one other batshit-crazy thing I found was that when I opened up a PDF in the desktop it took me to a TileWorld app and I couldn't figure out how to get back to the app I was in without clicking or swiping a bunch of times. Seriously? I have to manually enter custom file type associations just to use my desktop the way I've been trained to do it for 20 years? What year is this?"

Thankfully, I'm not writing a review of Windows 8…oh.

Anyway, the UI differences are certainly there, and they remind me of when Office 2007 came out. Upgrading Office to a newer version is something organizations had done many times in the past, but Office 2007 was the version that released the "ribbon" UI. Organizations held on to Office 2003 for as long as they possibly could, and despite the fact that Office 2003 reached end of mainstream support in April of 2009, I'd imagine many still run it to this day. Sure, a large chunk of that is because an upgrade would cost a small fortune, but the UI changes also factor in.

Now, take those UI changes in Office, plus all the education and end-user consternation that went into upgrading from Office 2003 and apply that to an entire OS. Yikes.

Aside from all of that, though, the underlying OS is still Windows. In fact, it's been said that Windows 8 performs as good or better than Windows 7 in many areas, and Microsoft certainly hasn't taken away any management capabilities. System Center is being updated to support Windows 8 and TileWorld applications (.appx apps). Unlike WinRT-based device (the ARM version of Windows 8), it can still be joined to domains and managed just as you would have managed any other version of Windows. Frankly, if Windows 8 didn't have Metro TileWorld, it would feel like a Service Pack or maintenance release, and I'd be all for migrating to it.

Windows To Go

Windows to Go, or WTG, is one of the features unique to Windows 8 that's generating some interest, although I can't think of a place where I'd like to use it in my routine (or any of my past jobs either, actually). WTG gives you the ability to deploy a Windows 8 image to a USB stick that can then be booted up in just about any modern PC. If it has USB 3, you're more likely to have a good experience, but anything that can boot from USB will work. 

The obvious benefit of this is that users can take their corporate-provisioned Windows desktop anywhere they go. Since a desktop booted to WTG doesn't have any exposure to the local storage on a computer, so there's no risk of cross-contamination. WTG can even be provisioned and managed by SCCM, which means we finally have a Microsoft-sanctioned, manageable way to boot Windows from a USB stick.

That said, where would you use it? I can't imagine people walking around with thumb drives plugging them into machines like bees searching for pollen. They'd get lost all the time, and I shudder to think about what would happen if any data was on the stick (which there most likely would be). The sticks can be encrypted with BitLocker, but since they're designed to be portable the device isn't tied to a specific TPM, which means that it's inherently less secure than using BitLocker on a traditional computer.

Perhaps the best use case I can come up with is for a user working from home. The user could take their corporate imaged thumb drive home with them and boot it up on their computer. The work image would be totally isolated from the personal OS and data, which alleviates the concerns that come with virtual machines running on Type 2 hypervisors or compromised PCs accessing remote desktops. To me, this is a pretty compelling scenario. There are others, like temporary workers or contractors, but they seem more like niche solutions.


The changes in RemoteFX warrant their own article, which is something that Brian did way back in February of this year. If you haven't seen it yet, check it out: Look out Citrix HDX & VMware PCoIP: RDP and RemoteFX in Windows 8 is awesome!

There are so many changes to note, like multitouch support and USB support for RDSH, plus game-changing things like honest-to-goodness WAN support due to the addition of adaptive graphics, UDP support, and advanced media remoting that will optimize and redirect any video in a RemoteFX session, not just Windows Media and DirectShow content.

Perhaps the best overall feature of RemoteFX in Windows 8, though, is that it just works. In the past, you needed to have a GPU on a Hyper-V host to use RemoteFX for VDI desktops, while terminal servers were able to use RemoteFX's features via a virtual GPU. The vGPU capabilities have now been added to Windows 8, so now you have the ability to leverage RemoteFX in any virtual desktop situation. Sure, you can still offload graphics processing to a GPU, but the bottom line is that RemoteFX is there for everyone to use now.


While there are some features of Windows 8 that are compelling, in the grand scheme of how we manage applications and data, deciding whether or not to use Windows 8 is going to be difficult. Do the new features outweigh the the challenge of the new UI? Sure, there are ways around the UI, but they're not officially sanctioned by Microsoft. Do we implement a work-around just to get at some of these features, deploy Windows 8 and educate the users on all the UI changes, or do we stick with what we have while we evaluate just what the next 3-5 years is going to do to the industry?

Many organizations are still struggling with how to deal with applications that they've deployed throughout their user base going forward. Many were burned by Vista and Windows 7 and have been forced to rewrite or replace them. In the past, the answer would have been to develop new apps in the Windows-based development platform-du jour, but with all the talk of a Post-PC era and the questionable decisions of Microsoft to have two application platforms in one OS make people leery of being burned again. That means that more and more companies are considering alternative platforms like browser-based, cloud-based, or mobile applications, and if you're not moving to Windows apps, why keep deploying Windows?

While others will surely protest this statement, I'm confident saying that Windows 8 will not be "Vista 2" in the Microsoft history books. The end result of "nobody's using it" might be the same, but I feel that the reasons for Windows 8's lack of adoption will be much different than those of Vista. Ripping out the Start Menu, changing the interface to Metro TileWorld, relegating the desktop to a second-tier interface, and creating two parallel-but-oh-so-different application execution environments is what will make or break Windows 8. The underlying OS, though, is reliable, optimized, secure, and manageable, which is more than we can say about Vista.

On the other hand, the industry is charging hard in a direction that Microsoft is only just now dipping their toes into. It might be too late, but Microsoft still has a lot of weight and money to throw around. On the other hand, the fate of Windows 8 is up to Microsoft because organizations faced with decisions about how to develop applications, manage applications, and manage data could always fall back on the fact that Windows pretty much just works the same way it always did. Organizations are moving to Windows 7 because they have to. The only way they'll move to Windows 8 is if they WANT to, and that will only happen after the evaluate all the other ways to develop and deliver applications and data. In the post-PC era, there are way more options than there used to be. Good luck with that, Microsoft.

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A few weeks ago Ballmer was interviewed by Reid Hoffman for the Churchill Club. They talked about many different things in our world, including Windows 8, touch, tablets, Office 365, and mobile devices. (A video is available, but you have to pay $9.95 for it. Totally worth it though.)

But when it comes to actual enterprise features of Win8, the only thing Ballmer kept pushing was WindowsToGo. (Which, again, I mean we've had that technology forever and it's always been a dud.. I can't see people knocking each over over for it now.)

Everything else, Office365, Office 13 collaboration, Skydrive, etc., is available to Windows 7. So I still can't possibly see a reason for a company to go that route? I mean heck, if you want WinToGo then use it for just your home users, or just buy MokaFive, Virtual Bridges, or whatever. I just can't see WintoGo being a driver.

Same with that other feature IT folks are excited about ReFS. You can't even boot to it, so again, it's cool for servers and database drives, but it's not pushing the enterprise desktop to 8.

And with Windows 7 support lasting through 2019 or 2020 or whatever, I can't see Win8 making an impact. Win9, yes.


So, I guess we're only going to upgrade to every other version of Windows now? :) Seriously, if the feature comparison isn't that great, then the ONLY reason we're upgrading is because support will be dropped.

. What happens when MS figures that out? 3 year product lifecycles?


Oh dear, deploying every other version with SA running at ~26% per'd be mad wouldn't you? Cue..."there's a lot more than upgrade rights to SA" response.


@brian You can boot from VHD on Windows 7 today giving you some of the same benefits as WTG, but as you said much better 3rd party options booting the corp desktop on home/BYOD PCs/Macs

@Gabe great points. There are a couple of points that I think bear mentioning.  Microsoft is betting you will want a unified experience with Windows 8.  Instead of having an Android phone, iPad tablet, and a Windows laptop you can have the "unified" experience on a WIndows Phone, Surface tablet and Windows 8 laptop. Maybe go further and eliminate at least one device by adopting a Surface pro or one of the new convertible tablet/laptop combos beginning to show up.

I do see the enterprise looking at Windows 8 specifically on the touch enabled mobile class of devices because it bridges a huge gap. There are a ton of Windows apps out there and until apps for enterprise are rewritten for iOS, Android, or HTML5 there is a BIG reason to give Windows 8 a try (though maybe not 100% switch like to Windows 7) in the interim.


Hey Matt - I've heard others talk about the touch-enabled mobile devices, too, but I swear it's the only reason. I've yet to hear anyone talk about the unified experience in the enterprise space. Have you, or is it just on the consumer side?


@Gabe I think the device reduction argument has interest in the enterprise. even from just a cost perspective. A decent Windows laptop + an iPad is what a  $400-$500 premium over 1 $1100-$1200 Surface Pro, Dell XPS 12, or similar. I don't think businesses will sustain paying for 2 devices with that kind of disparity forever. Somebody's going to lose.


I think Windows 8 has a chance in the enterprise for those users who currently have two devices - a laptop for content creation and a tablet for mobility.   They'll be able to use just one device that can be used as a tablet and/or PC.

A big difference between Windows 8 Pro tablets on IA and iPads, though, is that one is managed like a PC and the other is managed like a phone.  Which will enterprises prefer?


i don't want to be obviuous with all here cause i really respect you a lot and reading you from years.

But i need to alert someone of you, don't be be an angry old fashion geek style man.

I mean, Microsoft is operating something more important than just provide a new UI or tablet. They deeply change

the way that we think Windows. And the success is not to deliver a UI that you like or not, the objectives i think is to deliver

and offer a common plateform to push the new aera of world computing, i mean Cloud Computing;

I mean, the model that we are in now is the Server Based Computing with all the derivate associated like VDI,

but this model itself starting to operate a mutation that is part of the model itself.

And now the model is more like a Service Based Computing and The BYOD is just the "thinclient" of the model like the SBC model have pushed.

BYOD is the door for such an offer and Cloud Computing is the achievement of the architecture mutation.

All is bigger than ever. The World is open, too many web navigators, to many devices, too many phones, tablets...and big

company like MS need to embrace all of this people to let him survive is this worldwide competition engaged.

And private company couldn't fight against it.

One clic or Two and you will get a complete F5 BigIP on the AWS  !!

Remember Ed Iaccabucci from citrix in the early year, the fact is that you naturally tend to get something funtionnal as quick as

possible beacause your company need to survive too (i associate the computer to a "phone" utilisation : hang on, speak, hang off).

Microsoft is going the gain a hard challenge and from my point of view they need to go more ahead and burn definitively

"explorer.exe"...this is what they show on surface RT. Bill Gates always mention that the futur is the application.

And for sure Windows need to move from an "OS" statut to an Application Operating System for delivering apps and services.

Your phone is like that, your TV will be like that, your next computer or device will be like that.

Is the only solution to be a fast delivering company of service. No time to take 4 year to deliver a new OS !! it doesnt mean nothing now...

(sorry for my English..will be better next time..)

Best regards to you all !!


While I agree that the reasons to adopt Windows 8 are in the enterprise are slim. I wanted to point out a couple of improvements that may entice some to adopt it that haven't been mentioned above.

BitLocker is now included in Windows 8 Pro, so you don't need SA to use BitLocker anymore. That's a huge win for any organisation that doesn't pay for SA, especially if they have a hardware refresh coming up.

Also on the BitLocker front, there's a new option in Windows 8 for network-based unlock ( It does require UEFI, so it isn't going to be backwards compatible with all existing hardware and provisioning processes for that matter, but it is a nice usability improvement for BitLocker which means you can have security very close to as good as TPM+PIN security without having to use the PIN while on the corporate network. (For anybody that doesn't realize, while TPM-only based BitLocker is vastly better than using no encryption, there are too many possible avenues of attack to trust it for highly sensitive data because with TPM only encryption anybody can boot the system back into Windows and then attack the hardware or Windows itself rather than having to try to break the actual encryption).

And I personally think the UI concerns are overblown. No corporation rolls out a stock Winodws image. Windows 8 certainly requires more tweaking to make it corporate friendly, but I'm sure it can be done if a corporation has a reason to use Windows 8.

These features certainly aren't sufficient for most corporations to roll out Windows 8, but they may be important in certain cases.