Windows XP and Windows 7 Migration and Coexistence

windows7rc_bloglogo What do you need to consider when making the move to Windows 7?  If you are running Windows XP there are a number of items to worry about.  How do you migrate applications, personal data, etc.? 

We often focus our attention on the enterprise tools, but I thought it made sense for this article to focus on a single machine upgrade using a consumer point of view. There are some things you can and can’t do, so I thought I’d go on a little adventure to see what the road to Windows 7 was like.

Please note: I am not addressing most of the activation issues I see discussed on the internet. I did however research what we’ve publicly documented and published, and have provided several important references in this article.

Gathering the Resources

The first stop on my little adventure was the local OfficeMax.  I stopped by the retail store to purchase Windows 7 Professional Upgrade.  Yes, I actually spent real money and everything.  I know this seems odd, but I like to run the same thing you do and I don’t have upgrade media and keys with my TechNet subscription (which I find odd).

I decided to setup Windows XP on a fairly state-of-the-art laptop.  The victim in this case was a Lenovo ThinkPad. I could have used my oldest laptop or desktop, but it didn’t seem to make sense to deal with the slower speeds of those machines.  Windows 7 is already installed on my Dell Latitude D820.  I might as well use something newer and faster for testing.

I wanted to look at the issues associated with migrating to Windows 7 and using Windows Virtual PC XP Mode.  So I constructed some scenarios in my mind and set out to test them.  Some of my conclusions are probably wrong so I look forward to your feedback.

Moving to 64 Bit Computing

The version of Windows XP I installed was Professional but it was the 32 bit version.  It’s been a pretty long time since I’ve run Windows XP and hit the usual first issue.  I needed to grab the latest Intel SATA driver for my machines SATA AHCI mode and build a floppy disk for installation.  Brings back old memories.  Good old F6 at install time.  Glad that feature is now history.

The rest of the Windows XP install was easy enough.  I installed the integrated version of Windows XP and SP3 so updating it after that wasn’t too bad.  After I had the OS all ship shape, I proceeded to install a wide variety of applications and data.  I installed some old apps like Dreamweaver 8, and some new applications like Office 2010.  I installed some printers and copied my personal data.

When it was all said and done, I had a nice little Windows XP machine with a smattering of applications, connected printers, and user data.  The next step was of course to backup my work.  You never know how many iterations of testing you might go through so taking “snapshots” of your work along the way is smart.  In order to do that, I purchased Acronis True Image Home 2010.  Man, I really like that product.  Yes, I purchased it with my own money.  I’ve used Ghost for years but I’m really liking the Acronis product now.

So the question is, “Can I upgrade from Windows XP Pro x86 to Windows 7 Pro x64?”  The answer is of course yes and no.  To the best of my knowledge, we have never supported a cross architecture in-place upgrade (x86 –> x64).  And it can’t be done with Windows 7.  We also don’t support upgrading from Windows XP to Windows 7 even on the same architecture.  So what do you do?

Windows Easy Transfer (WET)

Before we get to the meat of the upgrade/install process, you should consider how you plan to move personal preferences, documents, music, pictures, favorites, etc.  Be sure to check out some of the steps the Windows Client team documented.  In my case, I skipped some of the upgrade checks and downloaded the latest and greatest transfer tool.

Head on over to  There are 32 and 64 bit versions for Windows XP and Windows Vista.  A word of warning here.  The version for Windows XP only gathers and creates the .MIG file.  In other words, you cannot use this tool to transfer this data into a Windows XP Mode virtual machine.  It does however migrate data to Windows 7 VERY nicely.  The user interface lets to pick and choose what to backup and restore at a very granular level.

If you plan to migrate data from Windows XP to a XP Mode virtual machine, you must use the Windows XP Files and Settings Transfer Wizard.  The problem with using this tool is that it is an all or nothing proposition.  You cannot pick and choose what is restored.  I have a better recommendation below for XP Mode use.

custom Custom Installation

When I did my Windows 7 Pro x64 Upgrade media install, I was offered two different choices by the setup program.  They aren’t overt choices but they are there.  The first is to install on the same disk and partition as the current installation of Windows XP.  If you do this, Windows XP, all of the apps, and all of the user data will be moved to a subdirectory called windows.old.

Keep in mind you are going to need a considerable amount of free disk space for all of this to occur.  In my case I am using a 250GB laptop drive and the Windows XP install, apps and data are only consuming about 35GB.  So I had plenty of available disk space.  The end result is pretty interesting for a couple of reasons.

First, grabbing your personal data from windows.old is fast and easy.  You can easily move your docs, pictures, music, etc. via cut and paste.  Since it’s all on the same drive, the move is nearly instant.  No waiting around for a wizard to pull the data out of a proprietary file format.

Second, when you delete windows.old you are left with nothing but Windows 7 and and personal data you decided to grab.  This is effectively a clean install at that point and because you did this in the supported way we expect, you should not hit any issues with the upgrade key activation.

I highly recommend using the windows.old method of custom installation because this seems to be the safe and effective approach.  You still have to install your desired applications into Windows 7, but look at the bright side.  You are starting off with a nice clean system and you can carefully evaluate which applications you really need.  We’ll talk about some application compatibility issues in a minute.

The other choice when using the Custom Installation option is to wipe the hard drive.  This involves formatting the drive and is obviously a destructive process.  You had better make sure you have working backups and copies of your data before going down this path.  See this article for the proper procedure.  See the Windows 7 Troubleshooting and Help area for other topics.  And by all means contact our support organization if you managed to get painted into a corner and need help.

xp mode Application Compatibility and XP Mode

An amazing number of tools and articles have already been written about how to move applications from Windows XP to Windows Vista and now Windows 7.  I am not going to go into all of that here because the topic is large and has already been covered in detail.  I would however like to mention something new.

We added some new capabilities to Windows 7 via a free download called Windows Virtual PC.  Windows Virtual PC lets you run a special Windows XP virtual machine that is tightly integrated with the Windows 7 desktop.

XP Mode will run a couple of ways.  As you can see at right, you can run the virtual machine windowed on the Windows 7 desktop.  You can also run applications that are executing in the vm but appear as if they are running native to the Windows 7 desktop.

When I first installed the XP Mode vm, I intended to use the Windows Easy Transfer wizard to migrate some settings from the original Windows XP environment of the physical machine to the virtual machine.  I learned the hard way this is not possible.  Thank heavens for taking backup snapshots along the way.  I then tried to use the Files and Settings Transfer Wizard but that wasn’t an ideal solution either.  It wanted to dump everything into the virtual machine and that IS NOT the intention of the vm.

Windows Virtual PC and XP Mode are intended to provide that last resort capability for one or two applications that simply won’t run otherwise.  It is not intended to be your production environment.  Therefore you should not need to use WET or the Files and Settings Transfer Wizard to migrate data to the XP Mode vm.  Use it for the one or two apps you require, but use Windows 7 for everything else.

Dual Boot

You can of course dual boot Windows 7 with another operating system.  This is also referred to as multiboot.  There are a number of methods to doing this and just for fun I decided to create a multiboot environment where Windows XP is on the original disk partition with Windows 7.

As you might have guessed, I installed Windows 7 using a native-boot VHD thus creating a multiboot environment.  That worked but keep in mind this is totally an unsupported configuration.  Let me repeat that.  As far as I can tell, we do not support a multiboot environment where Windows 7 is deployed like this.  If you want to learn how to do this, see the references below. 


Moving from Windows XP to Windows 7 can be very easy.  I realize I only touched lightly on the application compatibility topic, but as I mentioned above, there are many articles on how to solve app compat issues.  Many of those issues have already been solved by our partners and independent software developers.

As you can see above, there are a number of approaches to migrating or coexisting with Windows 7 and Windows XP.  I only looked at a single machine over the course of a couple of days.  For those of you supporting multiple machines, we do of course have a strong set of tools to help you assess your environment, automate the upgrades, and deploy Windows 7.  I’ll be writing more about the enterprise tools, but I thought you might enjoy the consumer tasks and tools first.


I actually recorded several screencasts during the research for this blog post.  In the end, I decided not to publish them.  The primary reason is because I felt the tools and techniques are pretty easy to understand.  That and my flabber was gasted when I learned the WET tool could not be used in the XP Mode virtual machine.  At that point it became apparent I had the wrong approach to XP Mode and simplified the tasks you might consider.  Feedback is welcome.

Other Information and References