Moving to Windows 7 while keeping one foot in the past

17 11 2009

I finally made the commitment to Windows 7 as my main OS on my tablet PC.  I’d been running it in a dual boot configuration for a while, but a few weeks ago, it was time to move on.  My Vista installation was over 2 years old and was starting to act unpredictably.

As with every fresh operating system installation, the pain of starting from scratch makes you swear to never let your machine get to its inevitable ugly state again.

Keeping that promise might be a little easier this time around though.  By using some cool virtualization technology, you can have the best of both worlds.

Easy transfer wizard

There are many discussions about how to make life a little bit easier when moving to Windows 7 by using the Microsoft Windows Easy Transfer wizard.  I discovered a few things that I didn’t know while using it and thought I should pass it along.

The first thing to know is that this wizard is really just a very specific backup application.  It will create an image of everything in your “Users” or “Documents and Settings” folder and your personal application and registry settings.  That means you may drag a lot of legacy information with you when you install a fresh copy of Windows 7, install your applications, and then re-run the transfer wizard.

1. Make a good, complete backup using Windows Home Server (WHS).  I’ve talked about that before.  It’s just a good insurance policy.

2. Move (or Copy and Delete) all your big files.  Pictures, videos, music should get copied over to an external drive, and / or your WHS.  In fact, going in that order will speed up the process (USB is usually faster than a network copy operation).

Your big files can hide.  For instance, if you use Windows Live Photo Gallery, you may have a really LARGE cache of “original images” that WLPG surreptitiously hides down in your \users\<user name>\AppData folders.  So copy those somewhere, or just delete them if you don’t care about them.  Note that the Settings and Transfer Wizard will back all of that up for you if you want to pick up exactly where you left off!

Also, the media transcoding folder of Windows Media Player or Zune might have many GBs of files in it.  Clean that out too.

Poking around your AppData folder may result in some discoveries – like your Temporary Files folder is huge, or your Outlook mail files are huge.  Using a folder size utility can help.

3. Compact your Outlook and Live Mail (I think you can just compress its folders) or Outlook Express mail files.  You might also consider creating a new personal folder (PST) for backing up items in your OST file and then deleting them out of the OST – there are times when your OST may have to be rebuilt anyway due to mail profile changes.  Emptying deleted items, sent items, and stuff like that prior to compacting will give you the best results.  Outlook can tell you what folders have the biggest footprint. My OST and PST files shrank dramatically (some up to 50%) after doing this.  This is a nice time saver for backup and restore operations too! 

4. Empty your Recycle Bin, make sure your Live Mesh is up to date – then remove this computer from your Mesh.  You may consider removing some or all of your documents from your Documents folder if you want to archive them.  Remember, once you add your “new” machine and install Live Mesh, your Meshed folder documents will come back.  I can’t guarantee that restoring your Mesh folders will result in anything but file collisions in Mesh when you try to sync your new Windows installation.

There’s more, but by now you’ve reduced the time and size of your Easy Transfer Wizard by many gigabytes and hours.  Some things surprised me, such as you couldn’t do a “partial restore” of some information.  You select what you want to include in your backup, but the restore just happens – no choices were available to me.  Also many non-Microsoft application settings are not backed up.

5. Re-install your applications – concentrate on the Microsoft ones.  Because many other applications don’t quite benefit the same way, you may decide to get most of your Office and Windows Live applications going, and start again with other applications.

6. Back up your new machine’s image PRIOR to running the Settings and Transfer Wizard.  If you decide that you hate what it did to your machine, or you need to install more applications you forgot, reverting to a fresh machine image from Windows Home Server sure beats reinstalling the OS again.

Making a lasting image

I didn’t want to re-pollute my new installation with lots of the things I only used occasionally.  I periodically use some pieces of software that are fairly invasive when it comes to space and registry settings.  Install enough of these and even the removal process will leave lots of junk lying around.

So why not keep that old OS install around “just in case”?  This is where VMWare comes into play. I’ve used this before, and it really came in handy – if you remember some key points.

1. Get a fast USB 2.0 hard drive (bigger than your current drive on your computer).

2. Download VMWare’s vCenter Converter Standalone software.  This is free and you’ll use it once.

3. Install it on your old machine after you’ve done all your backing up, transfer wizard, etc.

4. This is important – if you have a Dual Boot installation on your current machine, the conversion process will fail at 95% because VMWare is looking around your boot sector to determine how to boot your operating system.  You MUST edit your boot manager in Windows (or other OS).  In Windows Vista, this is NOT trivial (in NT to XP, it was just a text file).  Get DualBootPRO (pay – used to be free), EasyBCD (free so far), or brave it by hand (don’t do that). 

The irritating part is that you’ll probably just do this once or maybe twice, so paying for a utility feels a little dumb.  There are people who do this all the time, so it makes sense to have a full-featured version for that.

How ever you decide to do this, the important part is to BACK UP your current boot configuration, then REMOVE everything except the operating system entry you are backing up, making an image of, and then flattening with Windows 7.  You can always restore it after you use the VMWare Converter.  Windows 7 will disable your multi-boot configuration anyway – so you may need to use this tool once more.

5.  Once you finish step 4, you need to go through the VMWare Converter wizard.  It is fairly intuitive.  Make sure you set an appropriate amount of RAM for the image, and make sure the hard disk file you create has some spare space.  You can also turn services on and off in the image file – do NOT attempt to stop running services on the current machine itself.  I accidentally did that, and it just slows, or at worst, stops the conversion process.

6.  Go away for a while.  The process can take some time.

7. Once it’s complete, you will have a set of files and folders on your USB drive that will have an exact image of your running machine down to the desktop wallpaper.  It’s a BIG file and a few others (you can edit the machine configuration in Notepad if needed).  However, you can back it up elsewhere for safe keeping by just copying the files somewhere. 

But, don’t do that just yet.


The next step you can perform on a different computer or your existing one, prior to flattening it.  It’s a good thing to try booting it up once pre-wipe if you’re paranoid.

Download VMWare Player 3.x (2.x does not play well with Windows 7 – beware of frustration there).  Install it somewhere and point it to your USB drive.

When VMWare installs, it assigns a few “virtual Ethernet adapters” and sets one of them to  If your current router is handing out IP addresses on a 192.168.0.x subnet, you will NOT be able to access the Internet from your VMWare host installation.  Beware of this frustration as well.

The next part you ABSOLUTELY must know is that any Windows operating system will think that your VMWare image is a “hardware change”.  That means Windows will ask you to re-activate your operating system.  You only get a few activations, so be wise about this.

Two points to make here:

1. This could be a license violation because you have upgraded to Windows 7 (unless you bought a new copy).  However, this is just for insurance and is likely a temporary situation.  I’m not implying anyone should violate a license – knowingly or unknowingly.  My Vista license is on a development machine, so I should be OK.

2. You have 3 days to activate your machine.  The easiest way to activate is to get your virtual machine connected to the Internet.  You may have to switch your guest image’s network settings to “NAT” to quickly get an IP address.  Then, find the little “keys” icon near the clock in the bottom right of your screen and activate it!  If you don’t, Windows will start in a crippled mode, and if you didn’t get your Internet connectivity going – tough luck… you need to call the activation hotline and get a code over the phone.

Now that you’re done there, you can back up that image to a safe place (another disk) if you want, and you won’t have to re-activate it again.  If you back it up before activation, you will eventually become very suspicious to Microsoft.

You may want to disable some things like Automatic Updates, virus checkers etc. on your VMWare image (and try to keep it off the net).  Things like Windows Sidebar and utilities that start on bootup or login will only make your virtual machine painful to use.

If you have “Hardware Virtualization” in your machine that hosts the VMWare image, turn it on… it makes a difference.

So what?

For starters, if you want to keep your promise about not gumming up your new operating system installation, having an image of your previous computer around can help you resurrect the exact build environment or set of settings that may be dogging you on your new install.  Also, occasionally used applications can be easily accessed if needed.  To keep that image running well, “suspend” its image when you’re done with it rather than shutting it down.  Remember though: if you decide to use your VMWare image on another computer, completely shut the image down first.  You can’t recover a suspended image gracefully when you transfer a guest image to a new host.

In some versions of Windows 7, you are eligible to use the Virtual XP Mode that’s powered by Virtual PC.  You can install apps inside that image and use them natively in Windows 7.  This is probably the best (and most legal) way to fire up occasionally used applications.  If it works the way I think it does, this virtual image of XP will keep all the nasty DLLs and registry settings out of your lean and clean new installation!  I’ll be experimenting with that next.




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