Ingredients
Cookie Dough
- ¼ cup brown sugar (packed)
- ½ cup granulated sugar
- 1 cup butter (softened)
- ½ teaspoon sea salt
- 1 large egg yolk
- 2 teaspoons ground cinnamon
- 1 teaspoon pure vanilla extract
- 2 ½ cups all purpose flour (300g)
Pumpkin Pie Filling
- 1 large egg
- ¼ cup brown sugar (packed)
- ½ cup pumpkin purée
- 1 teaspoon cornstarch
- ⅛ teaspoon sea salt
- 1 teaspoon pumpkin pie spice
- ¼ cup evaporated milk
Whipped Cream Topping
- ½ cup heavy whipping cream (cold)
- ¼ teaspoon pure vanilla extract
- 2 tablespoons powdered sugar
Instructions
- Make Cookie Dough: In a large bowl or stand mixer fitted with a paddle attachment, combine the softened butter, granulated sugar, brown sugar, and sea salt. Beat the mixture until it is thick, creamy, and well combined. Scrape down the sides to ensure even mixing.
- Add Egg Yolk and Spices: Incorporate the egg yolk, ground cinnamon, and vanilla extract into the butter mixture. Mix thoroughly until the mixture becomes smooth and creamy.
- Incorporate Flour: Sift the all-purpose flour into the egg and butter mixture. Gently fold the flour in until a soft dough forms. Initially, the dough will be crumbly, but continue to mix until it comes together.
- Shape Cookies: Line a baking sheet with parchment paper. Scoop 1 ½ tablespoon portions of dough onto the sheet, forming balls. Press an indent into the center of each ball using your thumb. Gently press the sides of each cookie dough ball to create small walls to hold the filling.
- Chill Dough: Place the baking sheet with shaped dough balls into the freezer to chill while you prepare the filling and preheat the oven to 355°F (180°C).
- Prepare Pumpkin Pie Filling: In a medium bowl, whisk together the brown sugar and egg until combined. Add pumpkin purée, cornstarch, sea salt, pumpkin pie spice, and evaporated milk. Whisk everything together until smooth.
- Fill and Bake Cookies: Remove the cookie dough from the freezer and space them out on the baking sheet, leaving about 2 inches between each cookie to allow for spreading. Spoon 1 to 2 teaspoons of pumpkin pie filling into the indent of each cookie. Bake in the preheated oven for 12-14 minutes or until the bottoms turn lightly golden brown.
- Cool Cookies: Let cookies cool on the baking sheet for one minute after baking, then carefully transfer them to a cooling rack using a spatula. Allow cookies to cool completely before adding the topping.
- Prepare Whipped Cream Topping: For best results, chill your mixing bowl and whisk attachment in the freezer for 5 minutes before whipping. In a large bowl or stand mixer, combine cold heavy cream, vanilla extract, and powdered sugar. Whip with a wire whisk attachment until stiff peaks form—when the cream is thick, creamy, and holds its shape.
- Pipe Whipped Cream and Serve: Transfer the whipped cream to a piping bag fitted with a star tip, such as Wilton 1M. Pipe a dollop of whipped cream on each cooled cookie just before serving. Optionally, sprinkle a pinch of cinnamon or pumpkin pie spice on top for extra flavor and decoration.
Notes
- Chilling the cookie dough before baking helps the cookies hold their shape and prevents excessive spreading.
- Using cold heavy cream and a chilled bowl improves the whipped cream’s texture and helps it reach stiff peaks faster.
- These cookies are best served the same day with the whipped cream topping to preserve freshness and texture.
- For storage, keep cookies without whipped cream in an airtight container at room temperature for up to 3 days.
- You can prepare the cookie dough and pumpkin filling ahead of time and refrigerate before baking to save time on serving day.
- Prep Time: 25 minutes
- Cook Time: 15 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American
- Diet: Vegetarian