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Yup, This War of Mine kept me awake till 7 AM this morning. For some reason I'm drawn to games with extremely punishing fail conditions. Dwarf Fortress, XCOM, RimWorld, KSP...

I wouldn't say that KSP has punishing fail conditions. Other than things going BOOM horribly you can recover fairly easily unless you refuse to use the "revert to..." modes. Rimworld is just brutal, even on the easy settings (for me, anyways).

Holy crap those things are HARD. I am a newb so I started with casual settings and I was doing fine until two of those caterpillar things landed and proceeded to wipe out my entire colony. They are rough to deal with, even on easy settings. (And I am newb, lol).