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Windows 7 Review, Part 3: Installing, Upgrading, and Migrating

For the most part, Microsoft's supported methods for installing Windows 7 closely mirror those for Windows Vista. In some cases, such as the interactive Setup routine that very few people will actually use, the process has been simplified, in keeping with the general Windows 7 mantra. Elsewhere, however, life has become more difficult for users, especially those still running Windows XP who wish to upgrade their existing PCs. (This, too, is probably a pretty small crowd, relatively speaking.)

From a technological perspective, the Windows 7 Setup routine is simply the next version of the image-based Setup that debuted with Windows Vista and Windows Server 2008. It features the same basic installation phases, can be serviced and updated in the same ways, and supports in-place product edition upgrading. For this reason, all retail versions of Windows 7 include the code needed to upgrade in-place to a higher-end product edition. The product key included with the retail packaging determines which version you can activate.

Windows 7 installation choices

As was the case with Windows Vista, how you acquire Windows 7 largely determines the way in which you will install this new OS. Confusingly, there is a wide array of choices.

With a new PC beginning October 22, 2009

The simplest way to acquire Windows 7 is with a new PC starting on October 22, 2009, the day that Windows 7 becomes generally available. This will provide you with the absolute best experience, with one caveat: Many PC makers overload their machines with unwanted crapware, and this is absolutely still going to be an issue with Windows 7. Microsoft has made provisions for PC makers to modify the stock Windows 7 install in various ways, and while these controls are more restrictive than with past Windows versions, most of them amount to nothing more than recommendations that many PC makers will simply ignore. My advice here is simple: Take your business to those PC makers that offer crapware-less PCs, preferably those that do not charge extra for this "feature."

With a new PC before October 22, 2009

Those who purchase a new Windows Vista-based PC between June 26, 2009 and January 31, 2010 will typically qualify for a free version of Windows 7 through the Windows 7 Upgrade Option Program. When you buy a PC from a participating PC maker with Windows Vista Home Premium, Business, or Ultimate edition, you will later receive a free copy of the corresponding Windows 7 product edition (Windows 7 Home Premium, Professional, or Ultimate, respectively). The program is global; that is, it is available in all markets in which you can legally buy Windows-based PCs. Check with your PC maker before making a purchase.

That said, with Windows 7 set for general release in just a few months, you should hold off and wait for a PC that has Windows 7 preinstalled. Those who take part in the Windows 7 Upgrade Option Program will need to do an in-place upgrade as described below, which isn't a great experience. I've recently purchased a new Vista-based PC and will test the Upgrade Option Program upgrade experience when that package arrives.

Clean install: Full retail packaging

As with previous Windows versions, Microsoft is offering retail versions of Windows 7 in two forms, the more expensive Full packaging, which provides for both clean installs and upgrade installs of the OS, and Upgrade packaging, which I'll describe below.

In case it's not obvious, the Full versions of Windows 7 are aimed at those people who do not, for some reason, qualify for an Upgrade version. This isn't very common, as most people will have some copy of Windows 2000, XP, or Vista lying around, and each of them qualifies for any Upgrade version of Windows 7.

Rarity aside, there are two new wrinkles to the Windows 7 Full versions and both are sure to gain in popularity over time. The first is the ability to buy retail versions of Windows 7 electronically, via Microsoft's online store, the cunningly named Microsoft Store. The second is the ability to install Windows 7 from a bootable USB storage device, like a memory key, instead of a DVD drive. Netbook owners will be able to use these two new bits of functionality together to install the new OS on their machines, which typically lack DVD drives. (Oddly, Windows 7 does not permit installing to a USB-based storage device. I'm curious why.)

[ Click here to see a step-by-step guide to Windows 7 interactive Setup. ]

Upgrade and migration: Upgrade retail packaging

Contrary to the branding, the retail Upgrade versions of Windows 7 can be used to install the OS in a variety of ways. The word "upgrade" probably has a specific connotation for most people--i.e. the ability to run the installer in one OS and upgrade it, in-place, to the new version. And sure enough, the Upgrade versions of Windows 7 do allow for this traditional upgrade type, but only if the OS you're starting with is Windows Vista, and only then if you're upgrading to a compatible version of Windows 7. And that's where the confusion sets in. Not only can the Windows 7 Upgrade packages not upgrade a high-end Windows Vista version (like Ultimate) to a lower-end Windows 7 version (like Home Premium), it is also incapable of upgrading any version of Windows XP to any version of Windows 7.

This latter limitation is, in my mind, arbitrary, since the Windows Vista installer does allow such an upgrade, and the Windows 7 installer is, of course, simply a slightly refined version of that from Vista. After all, the Windows XP installed base is the largest group of Microsoft's customers. Why are they being treated like second class citizens?

Playing devil's advocate, I should at least point out that the number of people running Windows XP--an OS that first debuted 8 long years ago--who want to perform an in-place upgrade to Windows 7 on their aging PC hardware is likely pretty small. Most of these users would indeed be better served by installing Windows 7 on a new PC or simply purchasing a new Windows 7-based PC.

[ Learn more about upgrading and migrating in my series, Upgrading to Windows 7. ]

In any event, Windows XP users qualify for any Upgrade version of Windows 7, but they must instead perform what's known as a migration. In this type of upgrade, you use a utility called Windows Easy Transfer to copy the settings, documents, and data from your previous Windows install and then transfer them to a new Windows 7 install. This can be on the same PC (where you overwrite your previous XP install, or on a separate partition, in which you can dual-boot between the two OSes) or it can be with a new PC. What Windows Easy Transfer doesn't do, of course, is transfer your installed applications, so be sure you have your install discs and executables ready to go before performing this somewhat complicated procedure.

There is one other upgrade limitation that's worth pointing out since we're still in the midst of a multi-year transition to 64-bit computing. It is impossible to perform an in-place upgrade of any 32-bit version of Windows to any 64-bit version of Windows (and vice versa). So if you stuck with a 32-bit version of Windows Vista but are ready to take the plunge into 64-bit for Windows 7, you will need to do a clean install and then migrate your settings and data over with Windows Easy Transfer. (This is possible with the Upgrade versions, though the details of the process are unknown until I and other reviewers can get our hands on the actual upgrade packaging to test it.)

Working within Microsoft's arbitrary limitations, the following chart can be used to determine whether you can perform an in-place upgrade or must resort to a migration.

Current Windows version Upgrade or migrate to Windows 7
Home Premium?
Upgrade or migrate to Windows 7 Professional? Upgrade or migrate to Windows 7 Ultimate?
  32-bit 64-bit 32-bit 64-bit 32-bit 64-bit
Windows XP
(32-bit, any version)
Migrate only
Windows XP
(32-bit, any version)
Migrate only
Vista Home Basic
Upgrade or migrate Migrate only Upgrade or migrate Migrate only Upgrade or migrate Migrate only
Vista Home Basic
Migrate only Upgrade or migrate Migrate only Upgrade or migrate Migrate only Upgrade or migrate
Vista Home Premium
Upgrade or migrate Migrate only Upgrade or migrate Migrate only Upgrade or migrate Migrate only
Vista Home Premium
Migrate only Upgrade or migrate Migrate only Upgrade or migrate Migrate only Upgrade or migrate
Vista Business
Migrate only Upgrade or migrate Migrate only Upgrade or migrate Migrate only
Vista Business
Migrate only Upgrade or migrate Migrate only Upgrade or migrate
Vista Ultimate
Migrate only Upgrade or migrate Migrate only
Vista Ultimate
Migrate only Upgrade or migrate

*Note: In all cases where an true in-place upgrade is possible, you can optionally choose to do a migration instead as well. The reverse is not true, however.

As you can see, the upgrade picture is somewhat messy. Hopefully, by Windows 8, Microsoft will stop creating both 32-bit and 64-bit versions of its OS and just focus on the 64-bit side, though of course even that won't prevent the kind of bifurcated upgrade situation described above.

Windows 7 Family Pack

For the first time, Microsoft is finally offering consumers a way in which to purchase multiple copies of Windows at a discount. Called the Windows 7 Family Pack, this offering provides you with the ability to install Windows 7 Home Premium on three different PCs. (That is, the packaging offers one Setup disc and three product keys.) The Family Pack is a very reasonable $149.99 in the US.

As is so often the case, however, where Microsoft giveth, it also taketh away. The Family Pack consists of three Upgrade versions of Windows 7 Home Premium, so performing clean installs with this version will be somewhat ponderous. It's not available in all markets, either, and Microsoft says that it is a temporary offer only and could be pulled at any time. All that said, I expect the Windows 7 Family Pack to be quite popular, and hope--and request--that Microsoft make it a permanent offering, and one that is available to all of its customers.

[ Get more information about the Windows 7 Family Pack. ]

OEM versions of Windows 7

As with previous Windows versions, you'll be able to purchase so-called OEM versions of Windows 7 Starter, Home Premium, Professional, and Ultimate through online retailers like These versions of Windows 7 correspond to the Full retail packaging in that they cannot be used to upgrade existing Windows installs to Windows 7. However, because they are aimed at the system builder market (small businesses that build PCs for individuals), they are typically much less expensive than true retail versions. As always, there are a number of caveats. First, the availability of OEM versions of Windows to individuals is possible only through a loophole in Microsoft's licensing program; you are not actually supposed to purchase such a product for person use, though of course there are no real controls in place to prevent this. Secondly, OEM versions of Windows come with no support at all. So if you buy an OEM version of Windows 7 and run into problems, you're on your own. That said, anyone savvy enough to buy such a product for installation on their own PC can probably handle themselves. But it's good to know.

As of this writing, Windows 7 is not yet generally available, so we don't know exactly how the OEM pricing will compare to the Full and Upgrade retail packaging. If Windows XP and Vista are any indication, there will be serious savings to be had. I will update my Windows 7 Pricing article to address OEM pricing when that becomes known.

Windows Anytime Upgrade

As with Windows Vista, Windows 7 provides a special kind of upgrade called Windows Anytime Upgrade, that lets you take a version of Windows 7 and upgrade it in-place and electronically (i.e. without requiring a Setup disc or other external install point) to a higher-end Windows 7 version. A user with Windows 7 Starter could upgrade to Windows 7 Home Premium, Professional, or Ultimate, for example, while those with Windows 7 Home Premium could choose between Professional and Ultimate, and so on.

Unlike with in-place upgrades, I've found Windows Anytime Upgrade to be a fast and flawless way to upgrade your Windows 7 experience. Those who acquire Windows 7 Starter with a netbook should really look into this utility to upgrade to at least Home Premium. Prices range from $80 to $150, depending on which versions of Windows 7 you're upgrading to and from.

[ Discover how Windows Anytime Upgrade works in my Feature Focus article. ]


As with previous versions of Windows dating back many years, Windows 7 supports multi-booting (commonly called "dual booting," though of course you can install multiple copies of Windows on a single PC). Not much has changed here, though of course modern Windows versions like Vista and Windows 7 utilize newer and different boot processes, so the age-old advice still stands: You should always install the oldest OS first and the newest OS last. You should always install each OS to its own hard drive or partition. And while this may be obvious, it's worth noting that there is nothing stopping you from installing multiple copies of the same Windows version on a single PC, which can be valuable for testing purposes.

Multi-boot is, of course, a power user feature and there is some argument to be made that people who boot between an excessive number of Windows installs are probably wasting time and not getting any real work done. But the capability is there if you need it.

Virtualized Windows 7 installs

Finally, it's worth noting that the retail versions of Windows 7--that is, Home Premium, Professional, and Ultimate--are all licensed for installation inside of virtual environments like Windows Virtual PC, VMWare Workstation, and Hyper-V. Actually, Windows 7 Enterprise is also licensed for this use, and that version comes with a special extra bit of functionality: You are licensed to install the same copy of Windows 7 Enterprise in up to four different virtual machines, provided that each is installed on the same PC.

For individuals, virtualized Windows 7 versions will probably see the most use on Macs, where environments like Parallels Desktop and VMWare Fusion allow people to run Mac and Windows apps side-by-side, and in testing scenarios. But with Microsoft making a big virtualization push on the server, virtualized Windows installs will become more and more common in managed corporate environments as well.

Final thoughts

The hundreds of millions of people looking to upgrade to Windows 7 in just the next year or two alone have a lot of decisions to make. As noted previously, for the vast majority of users, the best experience to be had is with Windows 7 Home Premium (or higher) preinstalled on a new PC. But those who purchased a new PC in the past two or three years have ample computing horsepower to handle the new OS as well. The only question is how they will go about upgrading those machines to Windows 7. My sense is that the largest potential group of these customers--Windows XP users--has been left in the lurch, and I find that rather surprising. Those who are already running Windows Vista are in a better place from an upgrade perspective, and can choose between upgrading and migrating. (Most, I'm sure, will prefer an in-place upgrade.)

Looked at broadly, most of these problems are of Microsoft's own making; the company does not allow 32-to-64-bit upgrades across any Windows version, and it will not support in-place upgrades for Windows XP at all. And of course, the sheer number of Windows Vista and Windows 7 product editions makes the upgrade path hard to decipher and understand.

None of this diminishes the value of Windows 7. And these complaints should be taken within the context of the Setup advances Microsoft did make in Windows 7 around simplification and supporting true electronic version-to-version upgrades. But the sheer complexity of the Windows 7 upgrade process does make the very desirable act of moving to that OS a lost less seamless than it could be. And that's a missed opportunity, in my opinion.

Continue to Part 4: User Experience...

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