I was struggling to have SS1 working in multiplayer with win10. It worked ok at first, but after a while it lost sync and all the units freeze. Not the UI, just the units. Same behaviour in SS2.

After some debugging with the support, it turned out that one needs to set "Compatible with XP SP2" on the shortcut. Note that "XP SP3" does exhibit the same issue, just much later.

PS: huge thumbs up to the support that worked with me despite SS1 not being tagged "multiplayer".

Also, it works _perfectly_ fine with wine 5.0, that comes with Ubuntu 20.04. Be sure to :

1. Be sure you use a 32bit wine install: WINEPREFIX=win32 wineboot
2. install directplay with winetricks: winetricks directplay