Reinstalling Boot Camp Partition – Going from Vista to Windows 7 on an iMac

The time had finally come for me to switch my BootCamp partition on my iMac to Windows 7. The Windows Vista was just too unreliable and I heard a lot of good things about Windows 7. But of course you know that once you open things up, things can go wrong and it always takes longer than you expect.

First of course, back up the user data from Windows Vista and get TimeMachine up-to-date in case it all fails. Live and Learn Moment: I should also have rebooted off my Snow Leopard drive, run disk utility and repair/verify my iMac boot partition before starting.

My first instinct wanted to simply insert the Windows 7 disk and reboot and install a fresh install on the existing partition – some day when I am bored, I might try that and see what goes wrong – but this time I figured I would delete and recreate the partition through Boot Camp Assistant on the MacOS side. That seemed like the most upright thing to do.

So first I deleted the Windows Partition in Boot Camp Assistant, worked perfectly. That was the easy part.

Then I wanted to re-create the Windows Partition in Boot Camp Assistant. My first problem is that I followed directions and selected:

Download Windows support software for this Mac

This just does not work (per lots of forum posts) so I properly indicated that I had all of the drivers.

When I got to the part where it was going to re-create the Windows partition, using Boot Camp Assistant and after it took a long time with no explanation of what it was doing I got the following dreaded message:

Bootcamp Partition Error: “Files cannot be moved”

Urg, I just had a partition there – and so there was plenty of free space. At this point, I wish I tried booting my OSX drive and running verify/repair and see if that fixes the problem. I think it might have fixed the problem.

I did some goggling and came up with this discussion forum:

This led me to the iDefrag software. It turns out I had purchased iDefrag 1.x back in 2007 and throught it was a pretty cool product – I like nice clean disk space with files that have all their data in one place so I like defraggers. I even had a boot disk that I had saved from long ago in 2007. So I popped the iDefrag disk and booted – it worked, but not all of the options seemed functional.

So I messed around for a while and decided to by the latest iDefrag2. It nicely does not need to make a boot disk. So I rebooted into defrag mode and did a full defray. The drive heated up and so I aimed a fan at the back of my iMac to keep it cool. I did have to adjust the minimum temperature to restart the process to 52 degrees so the drive ranges between 52 and 55 degrees – but with the fan going, I don’t think it stopped for heat after I put the fan behind my iMac.

After defrag completed, I reboot and tried to create the Windows partition using Boot Camp Assistant and again after a long period of time, I got the

Bootcamp Partition Error: “Files cannot be moved”

I was distracted by a little red herring of a band of “red fragmented” files that were left at the end of the drive and I guessed that they might be the problem. So back to defrag and when I redefragged again the files were still there. Then I looked at the files using the iDefrag UI and they were:


Then I went into iDefrag in normal Mac OS mode, and the file was not there. Nice. It automatically gets cleaned up when it boots back into Mac OS/X. So that was *not* the problem – I had about 150GB free and empty and perfectly defrayed at the end of my 200GB drive and yet:

Bootcamp Partition Error: “Files cannot be moved”

Aargh. More googling. After I look for a few pages beyond the first few pages, I start to see mentions of “Repair Disk” and “fsck -fy” – then it dawned on me – that long pause when it was partitioning might have been a disk check.

So out comes the Mac OSX disk and boot into Disk Utility. Verify Disk indicates that I *do* have errors on the drive – so I run Repair Disk and fix the errors. Running Verify disk indeed indicates it is now clean.

Rebooting back into Mac OSX and running Boot Camp Assistant – I finally can make a nice 40GB partition and I insert my Windows Vista disk and am feeling pretty happy (having a defrayed boot volume just makes me feel happy in general).

But then as Windows 7 install completes and I am entering my activation key, it keeps claiming my activation key is wrong. DRAT! More Googling. Turns out you can leave the key field blank, finish install, and then activate online. Whew! I blank out the key and installation finishes.

I immediately try to activate Windows 7 using the Windows Activation Tool and after I enter my key and I wait a long time it tells me that my key is upgrade only. I look at the packaging that I got from the UM Computer Showcase where I bought the software and nowhere on the packaging is there any mention of “upgrade”. Ah well.

At this point, I am wondering if I just can buy another key. I did not want to reinstall Vista and then install Windows 7 over top of it and apparently they will not let you present the CD of the older product or the key from the older product. I want a fresh clean install – not with crufty bits hanging around from years earlier. And yes, I had a valid Vista Key.

So I am googling how to upgrade an upgrade key to a real key or perhaps beg Microsoft Support to give me a mulligan on this install.. And then I find this page about how to upgrade without installing Vista:

Oh yeah – you can upgrade over top of an Windows 7 installation (thanks for the loophole Microsoft! – I did not abuse it I just used it) – so I eject the CD and re-insert it and go through the upgrade process for Windows 7 (atop WIndows 7). During the “upgrade install”, it interestingly did a lot of copying of “files, settings, etc” so I was concerned that it was making cruft one way or another.