Preheat your oven to 350°F (175°C). Line a 12-cup muffin tin with paper liners to ensure the cupcakes don’t stick and are easy to remove after baking.
In a medium-sized mixing bowl, whisk together the flour, baking powder, baking soda, salt, and pumpkin pie spice. This ensures the leavening agents and spices are evenly distributed throughout the batter.
In a separate large bowl, whisk together the pumpkin puree, vegetable oil, eggs, and granulated sugar until the mixture is smooth and well combined.
Gradually add the dry ingredients to the wet ingredients. Stir gently until just combined; be careful not to overmix, as this can make the cupcakes tough. Divide the batter evenly among the muffin cups. Bake for 18 to 20 minutes, or until a toothpick inserted into the center comes out clean. Let them cool completely on a wire rack.
In a large bowl, beat the softened butter until creamy. Slowly add the powdered sugar, vanilla, and heavy cream. Beat until light and fluffy. Add a few drops of orange food coloring and mix until you reach your desired shade of bright Halloween orange.
While the cupcakes cool, assemble the hats. Place a chocolate wafer cookie on a flat surface. Use a small dab of frosting to “glue” an unwrapped chocolate kiss to the center of the cookie. Using a small piping bag with a fine tip, pipe a thin line of green or purple frosting around the base of the kiss to create a “ribbon” for the hat.
Frost each cooled cupcake with a generous swirl of the orange buttercream. Gently place one completed witch hat on top of each cupcake, pressing down slightly so it stays in place.