Preheat the oven to 350 degrees Fahrenheit and lightly grease four cups of a muffin tin.
In a bowl, beat the softened butter, granulated sugar, vanilla extract, and salt until smooth. Stir in the flour until a soft dough forms.
Divide the dough into four equal pieces and press each piece into the bottom and slightly up the sides of the prepared muffin cups.
In a separate bowl, beat the cream cheese, pumpkin puree, brown sugar, egg yolk, and pumpkin pie spice until fully combined and creamy.
Spoon the pumpkin mixture evenly into the four cookie-lined cups, filling each about three-quarters full.
Bake for 18 to 20 minutes, until the cookie edges are lightly golden and the centers are set.
Cool the cups in the tin for 10 minutes, then transfer to a wire rack to cool completely. Top each cup with a small dollop of whipped cream before serving.