These Pumpkin Pie Filled Thumbprint Cookies take the creamy, spiced pumpkin filling, sweet crust, and whipped cream of a traditional pumpkin pie and transforms them into easy pumpkin pie cookies! The shortbread cookie is so much quicker to make than pie crust from scratch, so you can make them for all of your Fall and holiday parties!
This simple cookie recipe uses a brown sugar shortbread thumbprint cookie base and a simple filling with pumpkin pie spice and puree. Top them off with whipped cream, and it's like eating individual mini pumpkin pies! I love these cookies even more than regular pumpkin pie, so I'll definitely be sharing them at Thanksgiving this year in addition to my Sweet Potato Cupcakes!
Why You'll Love This Recipe
- You'll only need 9 ingredients and won't need any fancy equipment to make these pumpkin pie shortbread cookies!
- You get all the goodness of pumpkin pie without the hassle.
- It's so fun to serve these individual pumpkin pie cookies - everyone gets their own mini pumpkin pie.
- The warm spices and pumpkin puree are the epitome of Fall flavors.
- To make the classic pumpkin pie filling, this recipe uses pumpkin puree. While you could make your own from scratch, canned pumpkin puree is equally as good and saves time and the mess! Make sure you buy pure pumpkin and not pumpkin pie filling.
- Sweetened condensed milk is one of my favorite ingredients because it adds sweetness, richness, and a great consistency to fillings and bakes.
- You can use store bought or homemade pumpkin pie spice. It's great to keep in the pantry so you can make other recipes like my Homemade Snickerdoodle Pumpkin Bread!
- These fall thumbprint cookies use brown sugar instead of granulated sugar which adds a slight molasses flavor typical in pumpkin pie. Light or dark brown sugar work in this recipe so use whatever you have on hand or favor!
See recipe card below for a full list of ingredients and measurements.
Substitutions & Variations
- Make a pecan pie variation by sprinkling finely chopped pecans on top of the pumpkin pie filled cookies before baking.
- Substitute chai spice mix in place of the pumpkin pie spice for a fun twist.
- Swap in cream cheese frosting for the whipped cream for a more decadent version of these pumpkin pie filling cookies.
This recipe has not been tested with other substitutions or variations. If you replace or add any ingredients, please let us know how it turned out in the comments below!
How To Make Pumpkin Pie Cookies
Step 1: In a large bowl of a stand mixer fitted with the paddle attachment or using a hand mixer, cream room temperature butter and brown sugar until light and fluffy. Add vanilla extract and mix until combined.
Step 2: Mix all purpose flour and salt into the wet ingredients until just combined.
Step 3: Scoop the shortbread cookie dough and roll it into balls. Place them on baking sheets about 2 inches apart, and press your thumb in the center of each dough ball to make a well. Chill them in the refrigerator or freezer while you make the pumpkin pie filling.
Step 4: In a medium bowl, whisk pumpkin puree, egg yolk, sweetened condensed milk, brown sugar, all purpose flour, and pumpkin pie spice.
Step 5: Fill the chilled, firm cookies with pumpkin pie filling and bake at 375°F for 10-13 minutes until the edges of the cookies are beginning to brown and the filling is set.
Step 6: Transfer to a wire rack and let the cookies cool completely. Before serving, top each pumpkin pie cookie with whipped cream.
- Use a scale to weigh the flour in grams (see "metric" tab in recipe card below) for the most accurate results. If you're using measuring cups, do not pack the flour it into them! Carefully spoon it into the measuring cups and level it off with a straight edge. Too much flour may make the cookie dough crack when you press down to make the thumbprint.
- Make sure your cookie dough is well chilled before filling and baking. This helps make sure that the cookies don't spread and the filling doesn't ooze over the edge.
- Fill the shortbread cookies with pumpkin pie filling as high as they'll go without spilling over the sides of the cookies! They'll look less full after they bake and shouldn't bubble over at all in the oven.
- Don't throw away your extra pumpkin puree! Transfer it to an airtight container, freeze it, and then defrost it for your next pumpkin bake. Or, whip up some Chocolate Pumpkin Muffins, No Bake Mini Pumpkin Cheesecakes, or Pumpkin Spice Coffee Cake right away!
Pumpkin puree only has one ingredient - pumpkin. It is cooked and pureed without any added ingredients. Pumpkin pie filling has added spices and is sweetened.
No. Evaporated milk is not sweetened and has a different consistency than sweetened condensed milk, so it cannot be substituted in this recipe.
This could be from over-measuring the flour. I highly recommend using a food scale to weigh it in grams (see metric tab in recipe card below). If you don't have a scale, carefully spoon the flour into your measuring cups and level it off with a straight edge - do not pack it into the cups!
Again, this is likely from over-measuring the flour. If this does happen and your dough is too dry, try adding an extra tablespoon or two of softened butter. It won't produce the best results, but may save the cookies in a pinch.
Store pumpkin pie cookies in an airtight container for up to 3 days. Add whipped cream right before serving.
Freeze baked and cooled cookies in an airtight container for up to 1 month. When ready to eat, place them on the counter for about an hour to thaw, then top with whipped cream.
Pumpkin Pie Filled Thumbprint Cookies
- Baking sheet
- Mixing bowls
- Measuring spoons
- Electric mixer recommended
- Cookie scoop 4 teaspoon capacity
- Cooling rack
Shortbread Cookie Dough
- 1 cup unsalted butter room temperature
- ½ cup brown sugar light or dark, packed
- 1 teaspoon vanilla extract
- 2⅓ cups all-purpose flour weighed in grams or spooned and leveled
- ¼ teaspoon salt
Pumpkin Pie Filling
- ½ cup pumpkin puree
- ⅓ cup sweetened condensed milk
- 1 large egg yolk
- 2 tablespoons brown sugar light or dark, packed
- 2 teaspoons all-purpose flour
- ½ teaspoon pumpkin pie spice
- whipped cream optional, for topping
Shortbread Cookie Dough
- In a large bowl, cream together the butter and brown sugar until light and fluffy (2-3 minutes with a hand mixer on medium speed). Mix in the vanilla extract well, then stir in the flour and salt until everything is combined well.
- Scoop and roll into smooth cookie dough balls (about 4 teaspoons each), then place them on a baking sheet about 2 inches apart.
- Press your thumb into the center of each ball to create a well. Be careful not to break through the bottoms of the cookie dough balls or filling may leak out.
- Chill the thumbprint cookies in the refrigerator or freezer until they're cold and firm. Preheat the oven to 375°F and make the pumpkin pie filling while they chill.
Pumpkin Pie Filling
- In a medium bowl, whisk together the pumpkin puree, sweetened condensed milk, egg yolk, brown sugar, flour, and pumpkin pie spice.
Assemble and Bake
- Carefully spoon pumpkin pie filling into each chilled cookie well, then bake at 375°F until the edges start to tan (about 10-13 minutes).
- Let cookies cool on the pan until firm enough to transfer to a wire rack to finish cooling. Top with whipped cream before serving (optional).
The provided nutritional information is an estimate per serving. Accuracy is not guaranteed.