What is this crossover of?

Nicely done and oh dear

Had a funny dream about the ending: that comet was actually not here but a puppet/plush like counterpart of him, a prank apperently. I think you can imagine Drill's reaction here

“Yes, you’re the forepony who saved that kid.”
“Mhm, and tried starting a petition but uh…” Drill rubbed his forehead, immediately regretting that he’d brought it up. “It…didn’t go anywhere.”

That's one way to put it.

“We don’t do these things to be evil, Drill, we do them because we’re pragmatic, and nopony’s going to care about morals when we’re all buried under ten hooves of snow.” Iron then fixed his glare back at Drill, which while may not have been intentional, was hard enough to bore a hole through his forehead.

As bad as it is, he has a point there.

Out of curiosity he sparred a glance and when he did his heart stopped.
Up high above clinging to one of the Generator’s external frames…
…Was Comet Trail.

He is just enjoying the view, right? ...Right?

Good chapter!
I enjoyed reading it.

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What is this crossover of?

It's a crossover with the video game "Frostpunk".
(A fact that should be considered to be put into the story description.)

In case you haven't see it yet check out this fantastic animation, a ponyfied version of the game trailer: