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So, the files and folders are getting transferred through somebody’s servers (privacy & security issues?) and are being uploaded then downloaded at what will likely be slow speeds compared to using a USB 3.0 external drive.

Maybe because it’s free?
I know that other transfer tools (such as Zinstall for example, which I personally prefer) can go locally via a cable, or even using a USB drive. Very fast, and no privacy concerns.

Use the Media Creation tool to create a USB drive with Windows 10 installer.
This way, you can force the upgrade.

You’ll find it here:
http://www.microsoft.com/en-us/software-download/windows10

Zinstall is a new one on me, but apparently they are in the running, and it will be interesting to hear if anyone has experience with it

The one catch seems to be that you need two drives (but not necessarily two machines) to use this means of moving from one to another. Now you have an excuse to buy an external drive, clone to that, migrate from that using the transfer software, then delete the clone, and use the new drive for backups and storage.

I used Zinstall exactly for this, with pretty nice results. You *can* use it to transfer from one machine to another, but you don’t have to. It supports real, in-place upgrade to Windows 10.

They even have a “Windows 10 upgrade” tutorial here.

Another option is to use the Media Download tool from MS. I was able to tell it to “download and upgrade now”, and it worked, without a USB key even.

I’d recommend using VirtualBox, which is free. You may even be able to run an existing XP Mode machine with it.