Description

Thick and chewy pumpkin pie cookies with a crisp bottom and a smooth, silky pumpkin pie filling. These big, well-spiced cookies offer a delightful blend of crispy edges and chewy centers, filled with warm pumpkin spice flavored filling, perfect for any holiday table or pumpkin lover’s treat.

Ingredients

Scale

For the cookie dough:

2 ⅔ cups all-purpose flour (337g)
1 tablespoon pumpkin spice
½ teaspoon salt
3 oz cream cheese, room temperature (86g)
12 tablespoons unsalted butter, room temperature (6oz)
½ cup granulated sugar (110g)
½ cup brown sugar, packed (112g)
1 large egg yolk, room temperature
1 teaspoon vanilla extract
⅓ cup coarse sugar for rolling (78g)

For the pumpkin filling:

1 large egg, room temperature
¼ cup brown sugar (56g)
pinch table salt
½ teaspoon pumpkin spice
¼ cup whole milk (2oz)
½ cup pumpkin puree (122g)
¼ teaspoon vanilla extract
whipped cream for serving (optional)

Instructions

Preheat: Preheat your oven to 350℉ (177℃). Line a cookie sheet with parchment paper and set it aside to prepare for baking.
Prepare the cookie dough: In a bowl, whisk together the all-purpose flour, pumpkin spice, and salt. Set this mixture aside. In a large mixing bowl, cream together the room temperature cream cheese, unsalted butter, granulated sugar, and brown sugar with an electric mixer on medium-high speed for about 3 minutes until fluffy. Scrape down the sides and bottom to ensure even mixing. Add the egg yolk and vanilla extract, then mix until fully incorporated. Gradually add the flour mixture in three additions, folding gently with a spatula after each addition to avoid dry pockets. The dough will be thick and should be cohesive.
Prepare the pumpkin filling: In a separate medium bowl, whisk together the large egg, brown sugar, table salt, pumpkin spice, whole milk, pumpkin puree, and vanilla extract until smooth and well combined. Set aside.
Form the cookies: Scoop the cookie dough into 2 tablespoon-sized balls (approximately 36 grams each) using a medium cookie scoop. Roll each dough ball in the coarse sugar to coat completely, then place them on the prepared cookie sheet about 2 inches apart to allow for spreading.
Create wells and fill: Using a 1 tablespoon measuring spoon (or the bottom of a small cup such as a Pepto Bismol medicine cup), press down on the center of each dough ball to form a well without breaking through the bottom. Fill each well with approximately 1 tablespoon of the prepared pumpkin pie filling, spreading gently to fill the indentation.
Bake: Bake the cookies in the preheated oven for 14 to 17 minutes or until the cookies are set and the bottoms turn a light golden brown. The filling should be mostly set but still smooth. Remove from oven and transfer the cookies to a wire rack to cool completely.
Repeat baking: Bake any remaining dough and filling in batches, ensuring the cookie sheet is cool before placing more dough balls on it to maintain proper cookie shape and texture.
Serve: Once cooled, optionally pipe or dollop whipped cream on top of each cookie. Sprinkle additional pumpkin pie spice or cinnamon for extra flavor and garnish before serving.

Notes

To create the well in the cookie dough balls, you can use the bottom of a plastic medicine cup similar to a Pepto Bismol cup for easier pressing.
Only add whipped cream to cookies you plan to serve immediately, as it does not keep well on stored cookies.
Store leftover cookies in an airtight container at room temperature for up to 3 days for best flavor and texture. For longer storage, refrigerate the cookies and bring them to room temperature before serving.
These cookies freeze well; store layered with wax paper between cookies in an airtight container.
Nutritional information is approximate and does not include optional whipped cream garnish.

Prep Time: 30 minutes
Cook Time: 15 minutes
Category: Dessert
Method: Baking
Cuisine: American

Keywords: pumpkin pie cookies, pumpkin spice cookies, thumbprint cookies, fall cookies, holiday cookies, pumpkin dessert, chewy cookies with filling