Go to properties on them and make sure they both have Windows XP service pack 2, reduced 16bit color mode, and run as administrator. Now you need to go RA2 install path again and find the game.exe and gamemd.exe. Simply run it and select RA2 form the list and patch it. Open it with notepad and only change 'NoVideoMemory' form 0 to 1 only. If you used an origin install, it's most likely in 'C:\Program Files (x86)\Origin Games\Command and Conquer Red Alert II' Included in that rar file was a dll file, but also a config file called aqrit.
Extract the rar file in the root RA2 folder. Then install and copy this ddraw file found here. Go to game properties and disable the Origin UI in game and also add '-win' in the command window above so the game will start in windowed mode. Head to the origin game page and find RA2. So it seems a combo of the different sulutions given here and there did seem to work with a few tweaks. I run the game on a Win 10 Pro 64bit system.
So I've been going back and forth about this for days now trying to get it to work.
