This was my first thought as well! I was weirdly obsessed with that game. It crashed all the time, so that part fits. I originally had the demo on CD, I think it came with X-Wing vs Tie Fighter or one of those other Lucasarts games.

I added more info here after others helped get more out of my head

[1]:https://news.ycombinator.com/item?id=33258294

The game was definitely a Win32 application so it wouldn't have the style of "The Dig"