Heat the oven to 350 degrees and line a baking sheet with parchment paper.

In a medium bowl, beat the softened butter and 1/3 cup granulated sugar until light and creamy.

Add the egg and vanilla extract, then mix until fully combined.

In a separate bowl, whisk together the flour, 1 teaspoon cinnamon, baking powder, and salt.

Slowly add the dry ingredients to the wet mixture and stir until a soft dough forms.

Mix the remaining 2 tablespoons granulated sugar with the remaining 1/2 teaspoon cinnamon in a small bowl.

Roll the dough into balls, then roll each ball in the cinnamon sugar mixture to coat evenly.

Place the coated balls on the baking sheet and flatten slightly with the bottom of a glass.

Use a pumpkin-shaped cookie cutter to form each cookie, then use a small knife or face-shaped cutters to add jack-o'-lantern features.

Bake for 10 to 12 minutes until the edges turn lightly golden. Cool on the sheet for 5 minutes before moving to a wire rack.