Microsoft Loses the Windows 7 Upgrade Battle

November 16th, 2009

Consider Microsoft’s plight. Hundreds of millions of customers, ranging from home users to the enterprise, bypassed Windows Vista and chose to stick with XP. Worse, many of them actually downgraded computers equipped with Vista, because they didn’t want to deal with its problems, real or imagined.

Without having the exact figures on hand, I think I’m safe in saying that the R&D costs spent to create Windows 7 are in the billions of dollars. Microsoft has a huge development staff to feed, and projects routinely take years to complete, even if Vista’s successor is mostly a refresh with some revised eye candy and a new name to counteract the stench of its predecessor.

You would assume, then, that Microsoft’s executives would really want to do everything they can to encourage their user base to dump an eight-year-old operating system and embrace Windows 7. Instead, they have made the upgrade path as draconian as possible. Instead of just putting the DVD in your PC’s drive, you have to first backup all your stuff to an external drive — assuming you have one — because you’re forced to do a clean installation to get the latest and greatest version of Windows.

The setup process will actually erase your PC’s hard drive, meaning that once Windows 7 is up and running, you’ll have to restore all your documents, and each and every application, assuming you even have the installers anymore. It’s very much different from the Mac, where installation files, even if they stretch beyond the Applications folder, are usually easy to find and copy to another drive.

Yes, Microsoft does include a utility to migrate your own files, and there are third party products that promise to simplify the XP to 7 upgrade mess. But there are no guarantees any of this stuff will really work reliably in the real world. No wonder computer shops are going to make a bundle selling you upgrade services.

Or you can just buy a new PC and put that old box out to pasture. While Microsoft doesn’t earn near as much money from each user license if you get Windows 7 preloaded on your new computer, they won’t be peppered with near as many support calls from disgruntled users.

On the other hand, the upgrade from Vista to 7 can, theoretically, be done in place without having to do anything more than sit back, click a few prompts and get on with your business. Well, at least that’s the theory, but the real world doesn’t always match Microsoft’s “head-in-the-sand” expectations. Or maybe they would rather not tell you.

Now consider what I tried to do this week after receiving a copy of Windows 7 Ultimate from Microsoft. You see, my particular installation of Vista Ultimate was done with VMWare Fusion 3.0, the recent major upgrade to their Mac virtualization software. My test Mac, by the way, is an Early 2008 Mac Pro with 16GB of RAM, running 10.6.2.

After the Vista installation was complete, I changed very few system settings beyond screen resolution. I also installed the latest Firefox, Opera and Safari to check how our sites appear on the Windows platform, plus the special bundled version of McAfee’s security suite supplied by VMWare.

So you’d think that a straight in place upgrade ought to proceed without difficulty. Well it would on any Mac even after far more system and application changes, but Microsoft is nothing if not inscrutable about such matters. What this means is that my Windows 7 installation was interrupted several times to warn me of potential compatibility issues.

What compatibility issues? Well, after closing the Windows 7 installation, I discovered a prompt from, believe it or not, Apple, to install QuickTime and Safari upgrades. Once that was done, I started the 7 installer again, only to be admonished to restart my PC to complete the installation of some unknown updates before trying Windows 7 again. After three failures, the installation actually began in earnest.

I won’t bother describing the process in detail. Except for somewhat prettier status screens, it’s not terribly different visually from Vista. Every process is frequently interrupted with “Please Wait…” prompts. I also ran into a few “Gathering additional information before expanding files” that were just as peculiar. Just what information does Microsoft need on a system that’s only a few steps from stock?

There were also several restarts during the process plus a notice that “Setup is upgrading registry settings” that had the usual frightening implications. Indeed, the dreaded Registry is one of the “features” that persists in Windows, despite being an endless source of performance bottlenecks, instability and general customer confusion. You’d think that Microsoft could manage to set aside a few billion dollars to just get rid of it and devise a settings database scheme that actually works.

In all fairness, I suppose some of the peculiarities might be attributed to running Windows in a virtualized environment rather than the real thing. On the other hand, neither VMWare nor Parallels ever presented problems installing Windows XP or Vista, so maybe it is a 7 thing after all, or just the consequence of upgrading an existing Vista setup rather than creating a new virtual machine.

At the end of the process, which consumed well over 90 minutes after the initial interruptions, Windows 7 restarted as a nearly virgin system. As you know, it doesn’t even include such basics as contact, calendar and even email software until you actually download and install the Windows Live Essentials files from Microsoft’s site. Talk about dumb!

While it’s too early to say much about Windows 7, I do agree with the critics that it’s noticeably snappier than Vista, with a more attractive interface. That doesn’t necessarily make it easier to use, and while I suppose it is more Mac-like, it doesn’t come close to replacing Apple’s operating system.

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23 Responses to “Microsoft Loses the Windows 7 Upgrade Battle”

  1. Andrew says:

    I absolutely disagree about in-place upgrades, Mac or Windows. I have never done an upgrade other than for experimentation, instead I always always ALWAYS do a clean install, regardless of platform or similarity to the outgoing version. I want my Snow Leopard just as pure and free of legacy non-Snow Leopard code as I want my 7 free of legacy Vista code.

    Would you do an in-place upgrade from XP came out in 2001, what was the current OS X back then? Puma? Assuming you could even run Puma on an Intel Mac, would you consider doing an in-place update to Snow Leopard on such a system? Heck, would you in-place upgrade from Jaguar to 10.5 Leopard? That is what you are asking Microsoft to provide, an in-place upgrade from a 2001 OS to a 2009 OS. Silly.

    • @Andrew, Consider Microsoft’s predicament with XP users. But when it comes to the Snow Leopard upgrade, Apple designed it for in place upgrades from Tiger and Leopard. And the success rate is extremely high.


    • Jocca says:

      I have always used “archive and install” with all my Os X upgrade and everyone of them went like clockwork without any hang ups. Meanwhile, Microsoft cannot even get rid of its registry in its latest operating system and that speaks volume about its inability to break the shackle from Window DOS foundation, despite the fact that it employs many times more engineers as Apple does.

    • John Davis says:

      @Andrew, installation of system updates on a Mac has never, ever been a problem and I’ve been using Macs since System 6. The only troublesome thing was the sheer number of floppies that you needed for an install of System 7.

      And since OSX, things have just been smoother than smooth.

    • Dennis Wall says:


      The SL installer is different than previous Mac installers in that it always does an archive and install by default. We are in the process of moving our entire company (about 100, mostly laptops) to SL. I’ve done 26 “in place” upgrades from 10.4 and 10.5 to 10.6 this week with NO issues. I can’t imagine the man hours this would take in an XP/Vista to Windows 7 environment.

  2. Jeff says:

    It goes beyond the lack of an in-place upgrade for XP. The tens of thousands of users that downloaded either the Windows 7 trial or release candidates, ostensibly the same exact OS, have to do a clean install. You can’t simply enter a valid Windows 7 license key and download whatever system components have changed via Windows Update. At best, you can do a custom installation and archive your old system, but it’s up to you to reinstall your applications and get your system up and running again.

    Dumb. Dumb. Dumb.

  3. Andrew says:

    Sorry guys, but in my opinion (and its just that, an opinion) ANY in-place upgrade is dumb. Clean install is always the safe bet. Lean, fast and stable, with no leftover droppings from a previous OS.

    Again though, Vista to 7 is a valid comparison to Leopard to Snow Leopard, but XP dates back to the Puma days, and I have serious doubts that even a Tiger or Panther upgrade from Puma, let alone Leopard would be far more trouble than its worth. Come on, fair is fair, upgrading to a 2009 OS from a 2006 OS is very different than from a 2001 OS.

    • @Andrew, Actually the comparison is not really valid.

      Obviously, Snow Leopard is only for Intel-based Macs, which can only run Tiger or Leopard as the previous operating system. With the PC, today’s hardware can use XP. Microsoft’s problem is that many XP users avoided Vista, but the upgrade from XP to 7 is messy. Microsoft surely has enough resources at its disposal to develop a tool that would automate the process, even if they can’t figure out how to build a proper in place installer. They chose not to do so, or maybe they don’t know how.

      Apple devised an installer that succeeds in providing in place Snow Leopard upgrades for the vast majority of Tiger and Leopard users. There aren’t many failures, and those would apply largely to systems heavily modified.


  4. Andrew says:

    I think MS just realizes that in-place upgrades from 2001 to 2009 technology will be too unstable, and thus don’t give the option. I wonder how many of Vista’s complaints came from in-place upgraders as that OS has been stable and fast since SP1 (on clean installs, anyway).

    I know SL only runs on Intel, but would you do an in-place upgrade form 10.1 to 10.5? 10.2 to 10.5? Probably not.

    • @Andrew, Consider:

      1. If it was possible, Apple would simply devise an installer that just replaced all the system files, so it wouldn’t be an issue. That’s pretty much what the Snow Leopard installer is doing.


  5. Karl says:

    I’m in the camp that a clean install is a better way. But why should it be and actually it looks like that is changing. Most of the software I use now updates in-place. Going from from Leopard to Snow Leopard was done with an in-place upgrade.

    Now I haven’t had an issues with doing the in-place upgrade with Snow Leopard. (Granted that doesn’t mean no one has.) But I do like in-place upgrades. They are extremely convenient. So I welcome the change and am glad that I don’t run Windows and have to wipe my hard drive clean.

  6. AdamC says:

    Out of context with this piece.

    I was listening to your discussion with Rob Pegoraro, he mentioned that
    Safari crashed all the time. I am using Safari with SL or rather I fact I am using the Webkit and Idon’t find it crashing all the time. It may hit the beach ball once a while but not all/every time.

    One thing I notice is tech writers have all the luck they encounter more problems than most ordinary users, even Om have better luck than me at getting bad stuffs from Apple – he was whining about the HD on his Mac Pro was bad not once but twice.

    Thanks for the time, btw an external HD can be used as the bootup disk for the Mac mini.

  7. rwahrens says:

    I’m with Gene on this one.

    I’ve been using the Mac since the days of system 3, and while the early OS X systems all allowed for clean installs, they also allowed for upgrades. Some I upgraded, some I installed clean, the first such being 10.1 and 10.2. Others were a mixed bag – Tiger I did a clean install, and also for Leopard – but SL, I did the suggested upgrade, and had absolutely no issues at all, other than the few odd apps that were incompatible with SL.

    I think that the better OS X code gets – i.e., the more Apple has tweaked it – the less a clean install is needed, unless they come up with something really new and groundbreaking. Although the Time Machine backups have been so handy and so reliable, that in reality, it doesn’t matter which you do – they are both as reliable as one can ask for.

    I do, however, always disconnect my TM backups from my MacBook when doing an upgrade – I remember that bug that wiped Firewire drives a few versions back! I then reconnect it when the installer asks if I’ve got a TM backup to draw files from. Easy, reliable and quick.

  8. Constable Odo says:

    Microsoft hasn’t lost anything major. In the past few years that Vista was a stinker, Microsoft lost maybe one or two percent desktop market share. They’re still the biggest tech company on the face of the earth and no company is even coming close. They still have a huge pile of reserve cash. Eventually all the Windows users will have to upgrade to Windows 7 because there aren’t any worthwhile desktop alternatives. All the existing Windows fanboy IT managers will eventually give in to Microsoft’s demands because Microsoft is all they know. Their whole careers exist only for Windows deployment and management. Once Microsoft discontinues XP support what else is left but to upgrade. Microsoft hasn’t lost any upgrade battle. It’s just quietly sitting in the trenches waiting for the suckers to surrender over time. Microsoft is an unbeatable company. It’s gone unchallenged for almost 35 years, so a few years of nearly no upgrades or difficult upgrades isn’t going to hurt it one bit. Microsoft has users by the short hairs no matter what hoops they make users jump through.

    I don’t think Microsoft wanted to give XP users an easy upgrade path. Microsoft probably wanted to punish users for running XP all those years and skipping buying Vista. Microsoft also realized that people running XP on those old machines wouldn’t be happy with Windows 7 on them and is likely trying to get low-tech users to upgrade to new hardware with OEM Windows 7 already on them.

    OSX clean installs are made so easy by Apple it’s a wonder why everyone doesn’t do clean installs. All you need is an external drive (or internal drive for machines with multiple bays). Just clone (free Carbon Copy Cloner) your old drive over to the external drive. Wipe your old drive clean and do a fresh install. Then you just use the Migration Assistant to pull your old User(s) and other data over to your newly installed OS. Always works like a charm. In my experience usually all the apps work (even the ones with serial numbers), Parallel and Fusion VMs, etc. Mostly all the bits and pieces of application installs reside somewhere in your User Library.

    • Pat S says:

      @Constable Odo,

      I call BS on the 35 years. MS DOS was developed in 1981 + 35 = 2016. The real domination of the OS market occurred when the pact between Microsoft and IBM fell apart in 1990 and Windows 3.0 became a marketplace success. Just because Microsoft won the desktop battle does not mean the alternatives is unbeatable. The company has stagnated as is losing share rapidly in the mobile market. Microsoft may have owned the 90s but look at their growth rates.

      As far as clean vs upgrade install. I have done upgrade install since 10.0 and have had no issues other then the crap which build up on a hard-drive over time. The advantage of a clean install is it acts like a spring cleaning, you can throw out all the junk you no longer need. I think the more likely path for those on XP is a new machine which by definition is a clean install, so Microsoft is not really targeting the retail customer rather the OEM for Windows 7.

  9. Sean says:

    I fully documented the same problems with Windows 7 installation on my Macbook Pro to show my PC fanboy friends. I counted 7 splash screen jumps and 3 black screens of DOS, or what ever it is called. I find it quite funny that this is considered an improvement over Vista. What a joke, it still jumps into a DOS/SCSI search at start-up. Why on Earth can they not hide this. It must be too tough for the engineers at Redmond.

    Then a buy Snow Leopard, for $30 bucks I might add, and had ZERO issues installing and running it. No funky splash screen jumps, no UNIX underpinnings jumping in my face, No need to wipe my hard drive clean EVER.

    Im sorry, but anyone defending Windows 7 is delusional at best, and just plain ignorant at worst.

  10. rwahrens says:

    Oh, come on, not that old saw about how unbeatable M$ is. Have you seen their latest quarterlies? Or the list of laid off employees?

    Lots of companies are switching, even if in small increments at first. The Agency I work for has been a huge, uncrackable wall of M$ crap for years, and we’re slowly installing Macs. I predict that as soon as we move to Exchange 2007 by the end of next year, it’ll turn into a flood, cause of Snow Leopard’s out-of-the-box support for that version.

    Plenty of folks have switched due to the XP-Vista-win7 debacle, haven’t you been listening? Fully half of all buyers at Apple stores are first time buyers of Macs (and have been for several years), and that is an exponential figure if it holds true as the raw numbers grow.

    Apple has a firm grip on the upper tiers of the consumer computer market – and that’s where the bleed over into the business market comes from. Don’t discount that halo from iPods and the iPhone, either – the move in my Agency to buy Macs is coming from the top executives – who started out with iPhones and all decided to try Macs next.

    And as for cloning your drive for that clean install? Why? Why go the extra steps?

    Time Machine backups are clean, accurate and easy. The installer even asks you if you have one to migrate data from, and when it’s done, the new install looks exactly like your old one – even to where you keep your icons on your desktop. Wasted effort to do the cloning, except as an off-site backup.

    Apple really does make it easy!

  11. ken h says:

    Probably should not have done this, but I have gone from Tiger all the way through to 10.6.2 without ever having done a clean install.

    No problems!

  12. Ken says:

    I have always done in-place upgrades with Apple and never hit a snag.

    The upgrade from XP to Vista is difficult because of structural changes, in the kernel, the directory structure, and the registry. Apple had the architecture right from the start, so they never had this problem. Microsoft knows the architecture needs revamping. They are in a transition period, and they are genuinely trying to move legacy applications into the future, but from the looks of it, they won’t be able to finish the transition before the end of the company.

  13. Craig says:

    I have never done a clean install on any of my Macs (dating back to OS 7) and have had no problems so far. With OS X, however, I do run Disk Utility’s disk and permissions repair then restart in safe mode prior to upgrading. I think I got the idea from MacFixit and don’t know if it helps much, but seems harmless at least.

  14. Louis Wheeler says:

    I have to wonder about the implications of all this. Microsoft could not have made this upgrade more inconvenient if they tried. It certainly goes toward arrogance.

    We don’t know how quickly Windows will be upgrading either. Nor will we have a real feel for it until February. Will Microsoft’s arrogance play a part?

    Here are the market share figures as of the week that System Seven was released.

    System Seven Beta — 2%
    Windows Vista — 6%
    Windows XP — 79%
    Windows 2000 — 3%

    The Vista and System Seven Users have every reason to upgrade. It is they who are causing big buys from Amazon, but that could taper off. It’s the others which I am concerned about. The Windows 2000 and about a third of the Windows XP users are on hardware which is too old to benefit from System Seven. These are special purpose computers in Enterprise and commerce which do a single task well and it is unlikely that they will be upgraded until the hardware breaks. And that could take five years.

    I’m guessing that about a third of the XP computers would benefit from System Seven, but they will be waiting for better IT budgets — perhaps as long as a year.

    So that leaves a third which will be moving to System Seven over the next six months or so. Hence, we have 26%+ 6%+ 2% which equals 34 percent of the computer market which will be moving soon to System Seven. That is about 340 million computers or upgrades, so that is a lot.

    There are a number of imponderables to consider. We don’t know how many XP users will switch to the Mac OS or Chrome OS. Some XP users may be ditching their XP computer for Net Books which use Linux. Stay tuned.

  15. Don says:


    – Which is easier to use, 7 or XP? XP is.
    – Which is faster, 7 or XP? XP is.
    – Which saves more $$$ & is easier on hardware? XP is.

    Why downgrade to something many times larger, several times harder, several times more confusing, but oh such pretty glass effects?

    Sure, 7 looks awesome. If looks could kill, this would be it! But in the real world, the wait to kill hung application timer just fails miserable & closes many apps before you even see them load. Just giving you time to see the end process button.

    7 compatibility with W98 or older OS just bombs out, while XP older OS support is in general, great!

    I just don’t see the need for a costlier OS that does things slower, wastes money, adds confusion & more clicks, doesn’t search external drives without going through hoops, doesn’t show all the files (hides files that XP shows with no problem, even when you check show hidden files, 7 still hides certain ones, even with view hidden system files… XP doesn’t do this!)

    No wonder everyone is so excited over XP, or even Ubuntu!

    7 is the Ultimate fail!

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