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Guastardo: I didn't purchased yet the GOG version of the game, as I already got it (but I'll take Gog version too, for convenience), but I think I can already share this tip: if the game fail to start on Windows 8 or 10, it can be a Direct Play problem.

Go on Programs and Features and click on "Turn Windows features on or off" (on the left), then go to "Legacy components", double click it, check the Direct Play checkbox and click Ok.

That's all, I hope this will help
It worked perfectly, thank you !
Does this help with installing the game from the disk? I recently had to upgrade to Windows 10 only to discover that my faithful original H&D2 disk seems to hang and not want to install. Reading around it looks like a Windows 10 security feature blocking older game disks with certain security software on them. Its a real bummer too as I've used my same original 2003 copy across multiple PCs through that time. Windows 7 ran it and most everything else perfectly.

Does this Windows 10 Legacy feature bypass the disk install problem?