Preheat your oven to 350°F (175°C) and line a 12-cup muffin tin with cupcake liners.
In a medium bowl, whisk together the 1 1/2 cups all-purpose flour, 1 1/2 tsp baking powder, and 1/4 tsp salt
1 1/2 cups all-purpose flour, 1 1/2 tsp baking powder, 1/4 tsp salt
In a large mixing bowl, beat the 1/2 cup unsalted butter and 1 cup sugar together using an electric mixer until light and fluffy, about 2-3 minutes.
1/2 cup unsalted butter, 1 cup sugar
Beat in the 2 large eggs, one at a time, ensuring each is fully incorporated. Add the 2 tsp vanilla extract and mix.
2 large eggs, 2 tsp vanilla extract
Alternate adding the dry ingredients and the 1/2 cup whole milk to the butter mixture, beginning and ending with the flour mixture. Mix until just combined; do not overmix.
1/2 cup whole milk
Divide the batter evenly between the prepared cupcake liners. Bake for 18-20 minutes, or until a toothpick inserted into the center comes out clean. Let the cupcakes cool completely.
Heat the 1/4 cup vegetable oil in a large, heavy-bottomed pot over medium heat. Add the 1/3 cup popcorn kernels nd sprinkle with 1/4 cup sugar. Cover the pot and shake it frequently to prevent burning.
1/4 cup vegetable oil, 1/3 cup popcorn kernels, 1/4 cup sugar
Once the popping slows to 1-2 seconds between pops, remove the pot from heat and sprinkle the kettle corn with 1/2 tsp salt. Pour onto a baking sheet to cool.
1/2 tsp salt
In a medium bowl, beat the softened 1/2 cup unsalted butter until smooth. Beat in the 1/4 cup caramel sauce and 1 tsp vanilla extract. Gradually add the 2-3 cups powdered sugar, one cup at a time, beating on low until combined.
1/2 cup unsalted butter
Add 2 tbsp heavy cream as needed to achieve a smooth, spreadable frosting. Beat on high for 2-3 minutes to make the frosting fluffy.
2 tbsp heavy cream
Once the cupcakes are cool, use a small knife or piping tip to carve out a small hole in the center of each cupcake. Fill the hole with premade 3/4 cup caramel sauce.
3/4 cup caramel sauce
Pipe or spread the caramel frosting onto each cupcake, covering the caramel-filled center.
Garnish each cupcake with a handful of homemade kettle corn for a sweet, salty crunch.