They say that a picture is worth a thousand words. Perhaps the same can be said of the right chart. The one below is so wordy I won’t have to write my usual 1,000-post. In reviewing the chart last night, I had one of those dreaded OMG moments.

My realization: After commandingly executing Windows 7 development, Microsoft had run off the track right before the finish line. Suddenly, Windows 7 is a disaster potentially like its predecessor. Could anything be worse than Vista?

Microsoft provided the chart to veteran tech reviewer Walt Mossberg, in response to his readers’ confusion about Windows 7 upgrades. If they were confused before, befuddlement must be their new state of mind. It sure is mine. The chart below comes from Walt’s “Deciphering Windows 7: The Official Chart” post.

Out of the 66 Windows 7 upgrade combinations, only 14 allow for an “in-place upgrade.” The others require a “custom install,” which basically means starting over and reinstalling all applications. Walt explains:

For most average, non-techie consumers whose PCs have a single hard disk, that will require a tedious, painful process with the following steps: temporarily relocating your personal files to an external drive or other computer, wiping your hard drive clean, then installing Windows 7, then moving your personal files back, then re-installing all of your programs from their original disks or download files, then reinstalling all of their updates and patches that may have been issued since the original installation files were released.

LOL, Microsoft finally has found a weapon against software piracy. Most Windows 7 upgrade installations will prevent people from keeping software they, ah, “borrowed” from friends, family, neighbors or the office.

Perhaps it’s Microsoft “hug our Windows OEM” strategy to sell more PCs, because what truly sane consumer would undertake the task Microsoft demands? It’s insane—more than any Vista lunacy—to ask most consumers buying upgrades to start over.

Windows 7 upgrade chart

Microsoft executives and evangelists talk about the Apple Tax. Here is the Microsoft Tax, not in real dollars but in time. How much is your time worth? You can always get more money, but time isn’t recoverable. Your one life passes before your eyes as you wait, wait, wait for the godawful upgrade and reinstallation process to finish. Microsoft taxes your time and temperament with burden.

I never, ever expected to write that Windows 7 might be a Windows Vista repeat, or worse. Never. In marketing, perceptions are everything. Early bad perceptions doomed Windows Vista to failure. Microsoft has set the table for Seven perception problems.

Most businesses and consumers keeping the same PCs will upgrade from Windows XP. Experience: custom install. During last week’s Microsoft Financial Analysts Meeting, CEO Steve Ballmer boasted about Microsoft’s netbook upgrade strategy. But netbooks running Windows 7 Starter Edition are custom install, too.

It’s the Vista upgrade scenarios that scare me, particularly custom install from Basic or Home Premium to Windows 7 Professional, which some small businesses, at least, will do. I find the 32-bit to 64-bit custom install scenarios puzzling still. I can understand custom install going from 64-bit to 32-bit. But why custom install going from 32-bit to 64-bit? Do you understand something profound here that I don’t?

Upgrades should be simple and easy, and leave the Windows buyer feeling better about the new version than the old. Tomorrow, Microsoft plans to release Windows 7 to MSDN and TechNet users. These are sophisticated users. If they fill the InterWebs with complaints about “custom install,” Microsoft has got a serious perception problem building. If not, a Vista-like perception meltdown will be averted, but not necessarily avoided.

Would you buy Windows 7 if your machine required “custom install?” Scratch that. Would you buy Windows 7 for your mom, dad or siblings if their PC required “custom install?”


  1. I would think that in the Windows-world going from 32bit to 64bit would mean having to do the following at the very least:

    Move all existing and installed 32bit apps’ registry data into the Wow6432Node registry sub-area from their current HKLMSoftwareetc location.

    Move all registered extensions, typelib entries, COM interfaces, etc that 32bit apps have loaded into the registry from HKCR to HKCRWow6432Node.

    Shared libs that naughty apps have placed into System32 would have to be moved to SysWOW64 (that’s right kids, SysWOW64 is the 32bit directory, System32 is the 64bit directory).

    All of this would be massively error prone, and please keep in mind that a lot of stuff needs to remain in all those 3 areas, so it’s not as easy as a bulk move.

    Please correct me if i’m mistaken with any of this.

  2. Hi Joe, Just my own 2 cents here…

    1. Simpler is always better. Part of the complexity in the chart is “legacy” complexity from vista that is casting a shadow over Windows 7 in this instance. The reality is that Windows 7 has cut the # of versions for consumers and small businesses down from 4 to 3. That’s progress towards simplification – the complexity comes primarily from the volume of FROM platforms, as well as the 32bit vs. 64 bit question. Which brings up my next observation.

    2. A lot of machines capable of 64 bit were sold with 32 bit OS (my Sony VAIO SZ among them). Quite an irritation if you paid for 4 GB RAM, like I did, BTW. I was thrilled to move to Windows 7 64 bit from 32 bit Vista. My guess is that MOST of the laptops sold running 3GB of RAM are 64 bit capable, but are actually running 32 bit Vista.

    3. About the time required for custom install of Windows 7 — where you breathlessly worry your life will pass before your eyes 🙂 — My personal experience was a great one. From start to finish, I was done and surfing the web in 35 minutes. That included validation, installing updates, connecting to wireless, all of it. Admittedly, copying the backed up data over to my hard disk did take a little while more but I just let that run and kept on surfing – no problems there. Breath deeply. 🙂

    4. I will say I’m not sure giving that chart to Walt was the best idea… it’s pretty comprehensive, but for some it may make things appear more complicated than they really are. Maybe a better option would have been to point Walt to a very simple html/javascript utility that lets people choose their existing OS, including 64 or 32 bit, from a dropdown list and then presents them with two categories in return: the list of OS versions they can upgrade in place and the list of versions they can custom install…?

    Would I like the process to be even simpler? I think so – but there are probably some trade-offs here, too. Maybe I’m not the average consumer, but I personally would prefer a clean install vs. an upgrade.

  3. Personally I think the biggest sticking points for most people are going to be the 32 to 64 bit migrations – among those will be mine. I’ve been using my desktop for over a year with 32 bit Vista even though I paid for 4GB. Yes Win7 is smooth as butter on this machine, and yes I do plan to install the RTM bits Friday after retrieving them from TechNet tomorrow, but I know the worst part of the experience will be tracking down and installing all the programs I have installed on this machine.

    Thankfully the laptop will be easier, since she’s staying at 32 bit for the time being…

  4. The “Microsoft Tax” concept that you have proposed Joe is very vital. The pain of reinstalling all programs and locating an external disk to temporarily store files is too huge. I have heard good reviews of the “Windows Easy Transfer” function in Windows 7. Maybe MS needs to build a version of this for XP and Vista too. Otherwise, as you have identified, this might be a huge bottleneck.

  5. The custom install has a significant benefit. It will remove all the crapware (most of which would not work in Win 7 anyway) accumulated over the years from the system and start clean.
    Realibility and performance wise this is great and worth the time spent for custom install.

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