I preheat the oven to 350°F (175°C) and line a baking sheet with parchment paper for easy cleanup.

In a bowl, I beat ½ cup softened butter and ½ cup granulated sugar with an electric mixer until creamy. I add 1 egg and 1 tsp vanilla extract, mixing well. I gradually stir in 1 ½ cups flour and ¼ tsp salt until a soft dough forms. I chill the dough for 15 minutes to prevent spreading.

I roll the dough into 12 balls (1.5 tbsp each) and place them 2 inches apart on the baking sheet. Using a teaspoon, I press a well into each ball. I bake for 10–12 minutes until edges are golden, re-pressing wells if they puff up. I cool the cookies completely on a wire rack.

I beat 2 oz softened cream cheese until smooth, then mix in ½ cup pumpkin puree, ¼ cup brown sugar, 1 tsp pumpkin pie spice, ½ tsp cinnamon, 1 tsp vanilla, and 2 tbsp heavy cream. I chill the filling for 30 minutes to thicken for Pumpkin Pie Cookies.

I spoon or pipe the chilled filling into the cookie wells. I top each with a small swirl of whipped cream and a pinch of cinnamon or nutmeg for a festive touch.

I serve the cookies immediately for the freshest flavor, enjoying their pie-like charm with a hot drink.