Can I update from Windows 95 to Windows 8, and then free upgrade to Windows 10

[Linnaeus]

My friend wants to try out a game but the prerequisite is Windows 10. Can he upgrade from 95 to 8, and then to 10? I'm using Windows 8 as a cheaper loophole instead of buying Windows 10 directly.

 

[basroil]

You cannot upgrade from 95 to 8, the only upgrade paths for 8 were Vista and 7. You need to buy a Windows 8 retail or OEM license. Once you do, you can do a clean install of Windows 8 and then you can upgrade to 10 just fine.