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DS1-LoA combined retail CD, originally installed on Windows XP. That machine died so I had to buy another September 2013, managing to get Windows 7 rather than 8, had to fiddle a bit I think (as advised elsewhere on this site) to get DS1 to work on Windows 7. From that point, the upgrade to Windows 10 was seamless. December 2015. (Seamless as regards Dungeon Siege. I had a bit of work to turn off Windows 10 backup, which would have quickly filled my little USB stick, and turn on Windows-7 style which is still supported. Also Windows 10 seems unwilling to update media - USB sticks, RW DVDs etc - which it hasn't formatted itself.)

While testing some of the legendary mod maps I've run through parts of the old DS1 ones just to remind myself how they are supposed to play out - the whole of Yesterhaven Act I for example, and bits of Utraean Peninsula. That is the vanilla DS1 launch - I've done little or nothing from the LoA launch on Windows 10.

What has made a difference, subsequently, is replacing the last peripheral retained from the old system, my monitor, by a new wider one, but that's another story. Fullscreen (I've never tried in a window) I have to run both DS2 and DS1 at 800x600 resolution because 1024x768 chops off a narrow band down the left of the screen - the character portraits! - while leaving a larger margin black on the right.