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Preheat oven to 300°F. Remove all unpopped kernels from popped popcorn. Place popcorn and pumpkin seeds into a 17x12x2-inch roasting pan. Keep warm in oven while preparing caramel.
Butter a large sheet of foil; set aside. For caramel, in a medium saucepan combine brown sugar, butter, and corn syrup. Cook and stir over medium heat until mixture boils. Continue boiling at a moderate, steady rate, without stirring, for 5 minutes more.
Remove saucepan from heat. Stir in baking soda and vanilla. Pour caramel over popcorn mixture; stir gently to coat. Bake for 15 minutes. Stir mixture; bake for 5 minutes more. Spread popcorn mixture on prepared foil and let cool.
In a small saucepan combine chocolate, shortening, ancho chile pepper, coffee powder, and cinnamon. Heat and stir over low heat until melted and smooth.
Drizzle chocolate mixture over cooled popcorn mixture; if desired, toss gently to coat. Let stand at room temperature or in the refrigerator until set. Break mixture into clusters. Spoon into gift container.