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Win10 Upgrade Score So Far: 10 attempts, 3 Failures (1 Fixed)

If you did a headcount of PCs here at Chez Tittel, you’d find only 8 of them. “So how is it that Ed has made 10 attempts?” you might be tempted to ask. The old saying: “If at first you don’t succeed,…” provides the answer, and also finally gives me some good advice to dispense for achieving a successful upgrade on one’s machines. At long last, a pattern has started to emerge, which suggests a time-consuming, but viable approach to getting problem machines to upgrade. The sanity of this approach remains open to question, but I have confirmed for myself that it works.

Here’s the deal: all of the machines on which I’ve had trouble performing an upgrade install have been upgraded from 7 to 8 and then from 8 to 10. My online reading and research shows me that the disk layout has changed over time, and that the recovery partition has added 150 MB (from 300 to 45o MB) as the OS has further matured. The only machines I’ve had problems with — and in each case, the symptoms have been the same, namely: the OS goes missing during the first reboot during the actual OS installation process (this is the second reboot in the overall sequence) at the 25% complete mark on the circular progress market — were those that did not get a clean install of Windows 8 after having been upgraded from Windows 7. All machines that came with Windows 8 pre-installed had no problems, and all machines that got clean installs of Windows 8 (and for the moment, that nomenclature encompasses both the original Windows 8 release and the 8.1 version that followed about a year later).

My advice in tackling the upgrade process therefore becomes: if your PC was upgraded from 7 to 8 and carries the old default disk layout with it(see the following figure for an example, taken from my wife’s PC which was upgraded from 7 to 8 a few years back) you would be well-advised to capture the OS key information, and then to perform a clean install of Windows 8.1 on that machine that includes wiping the drive and allowing the Windows 8.1 installer to create its normal default disk structure. You can wait to reinstall applications and so forth after applying all updates (120 as of my last count yesterday), and then performing the Windows 10 upgrade (use the Windows 10 Download Tool to avoid having to wait for an “upgrade slot” from Windows Update). This appears to work more or less flawlessly, so long as you’re willing to expend the time involved. In my case, this process takes about 4 hours per machine, but doesn’t require your undivided attention throughout (you can easily handle multiple systems at the same time, or also do other work while the PCs being upgraded grind through the many steps involved).

The layout that indicates a 7–>8 upgrade shows a 300 MB recovery partition at the head of the drive, and another 350 MB recovery partition at its tail.

The native Windows 10 layout starts with a 450 MB recovery partition, followed by a 100 MB EFI partition, and concludes with a “rest-of-drive” OS partition.

Assuming that you might want to follow my advice, here are some links to tools that will help you implement it:
1. Create installation media for Windows 8.1 (MS resource): use this if you don’t have a copy of Windows 8.1 to install at your immediate disposal.
2. Magical Jelly Bean Keyfinder: the free version will do the job nicely to extract your Windows 8.1 key. Warning! Most anti-malware packages, including Windows Defender, will block this tool as a form of malware. You’ll need to create an exception to its normal detection and blockage to use this tool. Use this to extract your Windows 8.1 key so you can enter it following a clean (re)installation of Windows 8.1. [Note: I myself use Gabe Topala’s excellent SIW Pro tool to extract Windows OS and other keys from my systems, but that tool isn’t free; lots of other tools are available to grab and store Windows OS and other keys: if you already have one at your disposal you don’t need to grab Keyfinder to enact this step of the process, but enact it you must.]
3. Once you’ve got a clean Windows 8.1 install at your disposal, you must apply all updates to that image before you’ll be allowed to perform the Windows 10 upgrade. This is the most time consuming step of the process, and will take anywhere from half an hour and up, depending on the speed of your Internet connection.
4. Use the Windows 10 media creation tool available from the Download Windows 10 page (MS resource) to build yourself a Windows 10 UFD from which to run your upgrade install from a clean version of Windows 8.1 to Windows 10.

Here’s the real deal on deciding what to do for your systems: it all depends on what value you put on your own time. If your time is worth more than $50 an hour to you, then you’ll be better off buying a $200 license to Windows 10 Pro and doing a clean install with a brand-new valid key. If your time is worth less than that, you’ll be better off doing the clean-install of Windows 8.1 to upgrade to Windows 10. Even so, I’m still inclined to follow that up with key extraction, and a clean install of Windows 10 on upgraded systems, just to make doubly darn sure to avoid further repetition of that pesky “OS is missing” error message when the NEXT big upgrade comes along! OTOH, it may be worth working with low-level disk management tools (such as Paragon’s excellent Hard Disk Manager 15 Professional) to see if some low-level disk manipulation might make these shenanigans unnecessary. I’m going to ask them, and see what they have to say on this subject…