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Pumpkin Thumbprint Cookies

Pumpkin thumbprint cookies with golden pumpkin spice shortbread and a filled center—creamy cream cheese or rich caramel. Rolled in cinnamon sugar and baked until set, then thumbprinted again by hand for the perfect hollow.
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Prep Time 25 minutes
Cook Time 14 minutes
Chill 30 minutes
Total Time 1 hour 9 minutes
Servings: 24 cookies
Course: Dessert
Cuisine: American
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 cup 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 caramel filling
  • 0.5 cup thick caramel sauce
Cinnamon sugar for rolling
  • 1 cinnamon sugar

Equipment

  • 1 sheet pan

Method
 

Make the pumpkin shortbread dough
  1. Beat the softened butter and sugar until smooth, then mix in the blotted-dry pumpkin and vanilla.
  2. Fold in the flour, baking powder, salt, pumpkin pie spice, and cinnamon until a soft dough forms, then refrigerate for 30 minutes.
Form and bake
  1. Preheat the oven to 350F and roll 1-1/2 tablespoon balls in cinnamon sugar.
  2. Set the balls on sheet pans, then press a deep thumbprint into the center of each cookie.
  3. Bake for 12-14 minutes, until the edges are golden and the centers look set.
Fill and finish
  1. Cool the cookies completely before adding filling, so the centers hold their shape.
  2. Fill the thumbprints with the cream cheese mixture or thick caramel sauce, then let set briefly before serving.

Notes

For clean thumbprints, press firmly right after rolling and again only if the dough seems to puff while baking. Store cookies in an airtight container in the refrigerator for up to 4 days; freeze baked, unfilled cookies for up to 2 months and thaw before filling. For a slightly lower-sugar option, swap the cream cheese filling’s powdered sugar for an equal amount of powdered sugar alternative used for baking (check label for 1:1 ratios).