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Preheat the oven to 225°F. Line a large baking sheet with parchment paper or a silicone baking mat. Set aside.
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Check the popcorn for any kernels, remove, then transfer popcorn to a large mixing bowl. Set aside.
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In a large, heavy bottomed pot, stir the brown sugar, butter, salt and corn syrup over medium heat until the butter has completely melted and is fully combined.
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Bring the mixture to a low boil over medium heat white stirring continuously to avoid burning and sticking. Once at a low boil, stop stirring and continue cooking for 5 minutes.
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Immediately remove from heat and stir in the baking soda and vanilla extract. The mixture will foam up rapidly (hence the need for the large, deep pot) but settle down quickly as you stir.
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Pour the caramel over the popcorn and use tongs to toss until the popcorn is evenly coated.
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Spread the caramel corn out on the prepared baking sheet and bake for 35 to 45 minutes, stirring every 15 minutes, until the popcorn has reached a deep amber color.
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Remove popcorn from the oven and allow the popcorn to cool completely.