The most frustrating bug I ever encountered isn't actually from a PC game but the PC hasn't been immune from frustrations. One notable jerk of a game is actually my beloved Deadly Premonition.
Even after trying to fix a bunch of its problems I encountered this huge pain in the ass bug which looked like it was going to prevent me from finishing the final fight because of clipping issues. Ultimately I "fixed" it but the fix was that in between QTE button mashing I was also having to repeatedly press Esc to rescue my character from inside the scenery where he was trapped.
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