In a small bowl, mix together all the ingredients for the churro sugar coating (powdered sugar, granulated sugar, and cinnamon), then set aside.
Prepare popcorn in a popcorn maker. You can also put popcorn in a paper bag, fold over a few times, then microwave for 90-120 seconds (or until popping slows). Pour popcorn in a large mixing bowl and set aside, giving it time to cool a little while you prepare the next steps.
In a medium saucepan, melt butter over medium heat. Add granulated sugar, cinnamon, light corn syrup, and vanilla. Allow ingredients to simmer, whisking constantly, until mixture is smooth and no longer grainy, about 2-4 minutes.
Begin to slowly pour cinnamon coating over popcorn a little at a time. Use a spatula to gently stir and toss the popcorn to coat.
Sprinkle the top of the popcorn with 1/3 of the churro sugar coating, then toss to coat. Continue adding more churro sugar coating until popcorn is completely covered and appears light gold in color.
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