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Pumpkin Thumbprint Cookies

Pumpkin thumbprint cookies with a tender pumpkin-spice shortbread base and a sweet center of cream cheese or thick caramel. The cookies are rolled in cinnamon sugar, baked at 350°F until golden, then filled only after cooling for neat thumbprint centers.
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Prep Time 25 minutes
Cook Time 14 minutes
chill time 30 minutes
Total Time 1 hour 9 minutes
Servings: 24 cookies
Course: Dessert
Cuisine: American
Calories: 95
Ingredients Equipment Method Notes

Ingredients
  

For pumpkin shortbread cookies
  • 2 cup flour
  • 0.5 tsp baking powder
  • 0.25 tsp salt
  • 1.5 tsp pumpkin pie spice
  • 1 tsp cinnamon
  • 1 lb butter softened
  • 0.67 cup sugar
  • 0.25 cup pumpkin blotted dry
  • 1 tsp vanilla
For cream cheese filling
  • 6 oz cream cheese softened
  • 0.33 cup powdered sugar
  • 0.5 tsp cinnamon
  • 0.5 tsp vanilla
OR use for caramel thumbprint filling
  • 0.5 cup thick caramel sauce
Cinnamon sugar for rolling
  • 0.5 cinnamon sugar

Equipment

  • 1 stand mixer
  • 1 sheet pan

Method
 

Make the pumpkin shortbread dough
  1. Beat the softened butter and sugar until well combined, then mix in the blotted dry pumpkin and vanilla until the dough looks smooth and cohesive.
  2. Fold in the flour, baking powder, salt, pumpkin pie spice, and cinnamon just until no dry streaks remain, then refrigerate the dough for 30 minutes.
Shape and bake
  1. Preheat the oven to 350°F.
  2. Roll 1-1/2 tablespoon balls of dough in cinnamon sugar so the tops are coated.
  3. Place the balls on a sheet pan with space between them.
  4. Press a deep thumbprint into the center of each dough ball so the well is clearly defined.
  5. Bake for 12–14 minutes, until the cookies are golden at the edges.
Cool and fill
  1. Cool the cookies completely so the centers set before filling.
  2. Fill each thumbprint with either the cream cheese mixture or thick caramel sauce.

Notes

For clean thumbprints, chill the dough for the full 30 minutes, then press the wells again lightly if they puff up before baking. Store cookies covered in the refrigerator up to 4 days; for best texture, let them sit at room temperature 15 minutes before serving. Freezing: freeze unfilled cookies up to 2 months, then thaw and fill. Dietary swap: for a dairy-free version, use a plant-based butter and dairy-free cream cheese alternative in the filling.