Preheat your oven to 350°F (175°C). Lightly grease a 24-cup mini muffin tin with non-stick cooking spray to ensure the cookie cups pop out easily after baking.
Divide your sugar cookie dough into three equal portions. Leave one portion plain (white/cream). Use the gel food coloring to dye the second portion bright orange and the third portion bright yellow. Knead the dough gently until the color is even throughout.
Pinch off a small piece of yellow dough (about 1/2 teaspoon) and press it into the bottom of each mini muffin cup. Follow with a layer of orange dough, and finally, a layer of the plain dough. The cup should be about 3/4 full in total.
Place the muffin tin in the oven and bake for 10 to 12 minutes, or until the edges are just set and the tops look matte. Do not overbake, as you want them to remain soft.
Immediately after removing the tin from the oven, use the back of a small measuring spoon to gently press down the center of each cookie. This creates the “cup” shape for the frosting. Let them cool completely in the pan before removing.
In a medium bowl, beat the softened butter until creamy. Gradually add the powdered sugar, vanilla extract, and enough heavy cream to reach a pipeable consistency. Beat until light and fluffy.
Pipe or spoon a small dollop of frosting into the center of each cooled cookie cup. Press one piece of candy corn into the top of the frosting. Your Candy Corn Sugar Cookie Cups are now ready to serve!