SOLVED Failure to update to 20H2 (no error messages)

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Info first: Toshiba Satellite L70-A, purchased in 2014, originally running Windows 7 Pro, currently running 10 1909.
Problem: this is my wife's laptop, and I’m her IT department. Yesterday, when I went to check for updates, I saw a message saying: "Your device is missing important security and quality fixes." However, nothing showed up after running "Check for updates," but there was a new message to the effect 1909 was no longer being supported. I did a few things suggested online to resolve the problem, but none worked. Since one suggested updating to the latest version of Windows, I decided to try that. I had not done so until I had some time with 20H2 on my computer to feel comfortable with its stability (didn't want her to be down). However, after going through VERY lengthy processes of “Getting things ready,” “Downloading,” and “Installing” twice, both apparently successfully, checking the OS Build still showed 1909!
Computer too old? If so, since 1909 gives her everything she needs, any ideas on getting rid of the “Your device . . .” indicator?
 
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However, after going through VERY lengthy processes of “Getting things ready,” “Downloading,” and “Installing” twice, both apparently successfully, checking the OS Build still showed 1909!
Don't see in there about rebooting/restarting the computer, necessary to complete the Version Upgrade. Some Build updates to the Version also require restarting.
 
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Done whenever requested, as well as powering down overnight and rechecking this AM.
 
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Computer too old?
Shouldn't be but possible. But a question, did you notice the Build number each time you checked the Version, could be you were only getting updated to get ready for the latest version. I have had that happen with a few older installs, usually needed 2 updates first.
 
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OK -- had to wait for wife to finish class on Zoom. Build 18363.1556. Ran Update Troubleshooter -- no fixable issues detected.

While I was waiting, I thought I'd investigate me buying something new and giving my wife mine. Quickly found I'm definitely in the "T-Rex" mode! No optical drives (that one I can work around), no port, either RGB or DVI, for my external monitor, no port for my LAN cable, and seldom, if any USB-A ports, for the 10 devices I currently have requiring such a connection (only one of which is wireless-capable).
 
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I have a Toshiba Satellite as well, purchased in 2008 and it runs 21H2 Insider version as well as the latest 20H2. I did some checking on your laptop and it should run the latest version with room to spare, so to say.
Have you used the upgrade assistant or the MCT to upgrade??
My other laptop, I am writing this on it, is even older, however it is stuck with Version 1803 due to hardware issues. I always get the message that my version has reached end of service and that I should update. So far I was always able to prevent the updates and MS has not bothered me in a long time....

BTW: Version 1909 officially has seen the last update this month, however most of the time there will be one or two more monthly updates before they seize to come in.
 
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The current Version 20H2/2009 has Build 19042.985 so yours appears pretty old.
Build 18363.1556 for Windows 10 version 1909 servicing/support for it has ended.
The servicing usually is 15-18 months from release.
Got that -- that's why I'm trying to update. But, as I said, getting nowhere. "Grizzly" asked if I was using the Upgrade Assistant or MCT. Presuming I'm using the assistant when I try to do it through PC Setting "Upgrade & Security," what's the MCT?
 
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MCT = Media Creation Tool, a free tool that when run goes to a Microsoft site to download Win10. It can get an .iso file used to burn a DVD that is an exact copy of the original [can be used with other software]. The USB choice creates/writes a USB Thumb drive which becomes bootable if the BIOS supports it, has Legacy USB Enabled. I use an 8GB thumb drive, the .iso file is now needing a DVD+R/DL [Dual Layer] disc that may not be locally available, the Wal*Mart nearest doesn't always have them so I order online, Verbatim has proven good for me.
 
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Tried to do so on my computer (already running 20H2 19042.985) to create the tool and then use on the laptop in question, but just get "Thank you for updating to the latest version of Windows." Do I need to do this on my wife's laptop itself?
 
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Ah -- hit "Update now" instead of "Download tool now!" Going forward now -- will report success (hopefully) later.
 
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Hmmm... Created flashdrive, and booted from it. Got to "What type of installation do you want?" Chose "Update: Install Windows and keep files, settings, and applications" (rather than "Custom: Install Windows only (advanced)". Dialog box opened: "Compatibility Report: The upgrade option isn't available if you start your computer using Windows installation media. If a copy of Windows is already installed on this computer and you want to upgrade, remove the installation media and restart your computer. After Windows has started normally, insert the installation media and run Windows Setup."
 
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Compatibility Report: The upgrade option isn't available if you start your computer using Windows installation media. If a copy of Windows is already installed on this computer and you want to upgrade, remove the installation media and restart your computer. After Windows has started normally, insert the installation media and run Windows Setup.
that is exactly what you need to do...
 
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All understood and complied with, up to "run Windows Setup." What exactly does this mean? I tried executing the "setup.exe" file on the flashdrive root menu, but that simply brought me around to the same place. Sorry to be asking so many (probably dumb) questions.
 
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The setup.exe in the root directory will start the Windows setup. Since I do not know what your flash drive contains (mine always have the 32bit AND the 64bit version on it) you might go in the appropriate folder of your architecture (32bit or 64bit) and start the setup.exe from there, it does not make a difference though. Since you start the "Upgrade" procedure from the USB drive, the setup will check what you already have on your PC and start the correct procedure (at least it should do it like that)...
 
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I created the flash drive using MediaCreationTool20H2.exe, and is only 64-bit, based on the "Select language, architecture, and edition" box. However, I had done so on my computer (already running 20H2). I thought: "What the heck -- maybe I should try creating it on the computer in question?" I did so, and ran setup.exe from root directory. Process appeared to started OK, so left overnight to (hopefully) finish. Woke up this morning to find the normal desktop, with 20H2 being reported in PC settings/System/About! Just needed some hand-holding. Thanks, guys!
 

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