Preheat your oven to 350°F (175°C) and line your baking sheets with parchment paper.

In a stand mixer, combine softened unsalted butter and powdered sugar. Beat until light and fluffy, about 3-4 minutes.

Gently mix in the vanilla extract until fully combined.

Gradually add the all-purpose flour and mix on low speed until just combined.

Divide the dough in half and color one half with orange food gel and the other with yellow food gel.

Roll the colored dough into 1-inch balls and place on the baking sheets, pressing your thumb into the center of each ball.

Bake for 14-16 minutes, until the edges are set and lightly golden. Re-indent if necessary after baking.

Heat heavy cream and candy corn in a saucepan until the candy corn melts, strain to remove solids. Add butter and stir until smooth.

Combine granulated sugar, light corn syrup, and water in a clean saucepan. Cook over medium heat until deep amber, about 10-12 minutes.

Carefully whisk in the cream mixture to form the caramel filling.

Once cookies have cooled slightly, fill each thumbprint generously with caramel. Top with mini candy corn if desired. Let set at room temperature for 1 hour.