These pumpkin pie cookies feature buttery thumbprint cookies filled with spiced pumpkin pie filling. It’s a fast and easy recipe made with a no-chill cookie dough that goes straight from the mixing bowl to the oven!

Pumpkin pie cookies with pumpkin puree and cinnamon sticks.

These cookies are a fun spin on my classic thumbprint cookie recipe, but instead of jam they’re filled with a spiced pumpkin pie filling to make them taste just like the classic pie.

The cookie dough is a shortbread-like dough, but it’s incredibly soft and easy to bite into. It also comes together in just one bowl and doesn’t have to be chilled before baking either (win-win!).

These cookies are delicious on their own, but I also love to add a little bit of homemade whipped cream on top. Set out a plate of these pumpkin pie cookies for Halloween or Thanksgiving gatherings, gift them to a loved one, or just keep the entire batch for yourself!

Recipe Video

Pumpkin pie spice, egg yolks, and pumpkin puree in separate bowls.

Ingredient Notes & Substitutions

Egg Yolks

This recipe calls for two large egg yolks in the cookie dough, which keeps the cookies super soft and tender. You can save the egg whites and use them for breakfast the next morning or in another recipe, like my candied pecans. You’ll also need a whole egg for the pumpkin filling.

Pumpkin Puree

Be sure to use pumpkin puree for the filling (I always use Libby’s!). Just make sure you don’t accidentally grab a can of pumpkin pie filling because it’s already spiced and sweetened.

Pumpkin Pie Spice

You can make your own pumpkin pie spice or buy your favorite blend from the store. I only used ½ teaspoon in the filling, but if you love spice feel free to add more!

Tips For Making The Cookie Dough

  • Make sure your butter is softened properly. Instead of letting the sticks of butter sit out until they’re super soft and greasy, place them on the counter about an hour before you plan on making the cookies. You want the butter to be at a cool room temperature; your finger should easily make an indent, but not slide around.
  • Mix the butter and sugar together long enough. It should take about 1 to 2 minutes to properly mix them together.
  • Use room temperature egg yolks. Room temperature ingredients will mix more evenly, creating a smooth and uniform dough. If you forget to bring your eggs to room temperature, just place them in a bowl of warm water for about 5 minutes before cracking them open.
  • Measure your flour correctly. If you scoop the flour from the container, you’re likely going to end up with too much and a dry, crumbly cookie dough. I either recommend using a food scale or spooning your flour into the measuring cup and leveling it off with the back of a knife. If you’re new to baking, I have a blog post that explains more about how to measure flour correctly.

Heads up: this is a thick dough! It may seem crumbly at first, but it does come together as you keep mixing. You can work it together with a rubber spatula or your hands if needed (just be sure not to use your hands too much so it’s not too warm).

How To Shape And Fill Your Cookies

Filling thumbprint cookies is easy, but you do need to be a little patient because it does take some extra time. I suggest rolling each ball of cookie dough in granulated sugar first. It not only adds a little extra sweetness and crunch, but it will keep your measuring spoon from sticking when you make the indentation too.

To make the indentations, I like to use the bottom of a ½ tablespoon or a teaspoon measuring spoon. You can use the handle of a wooden spoon or your thumb instead, just be sure to work it around until you have a nice, deep well so you can fill each cookie with a good amount of pumpkin pie filling.

If the dough cracks as you’re shaping it, you can use your hands to kind of work it back together. Then, just spoon the pumpkin filling into each indentation. I like to fill them as close to the top as I can get, without it spilling over the edge.

Can I Make The Dough Ahead Of Time?

Yes, you can make and chill the cookie dough for up to 3 days.

When you’re ready to shape and fill the cookies, let the dough come to room temperature (or until it’s easy enough to handle and shape). If it’s too cold, it will be more difficult to shape.

A pumpkin pie cookie with whipped cream on top.

Like I mentioned earlier, these cookies are delicious with a little whipped cream on top. If you want to try something else though, I think my pumpkin spice whipped cream would be delicious too!

If you make these cookies, don’t forget to leave a star rating and comment below telling me how they turned out. Happy Baking!

A pumpkin pie cookie with a bite missing.

Pumpkin Pie Cookie Recipe

Prep Time: 40 minutes
Cook Time: 15 minutes
Total Time: 55 minutes
These pumpkin pie cookies feature buttery thumbprint cookies filled with spiced pumpkin pie filling. It's a fast and easy recipe made with a no-chill cookie dough that goes straight from mixing bowl to oven!

Ingredients

Servings: 24 cookies

Thumbprint Cookies

  • 1 cup unsalted butter softened (226 grams; 2 sticks)
  • ⅔ cup packed light brown sugar (135 grams)
  • 2 large egg yolks at room temperature
  • 1 teaspoon pure vanilla extract
  • ¼ teaspoon salt
  • 2 ⅓ cups all-purpose flour spooned & leveled (290 grams)
  • ¼ cup granulated sugar optional (50 grams)

Pumpkin Pie Filling

  • ½ cup pumpkin puree (115 grams)
  • ¼ cup packed light brown sugar (50 grams)
  • 1 large egg at room temperature
  • 2 tablespoons heavy cream
  • ½ teaspoon pumpkin pie spice
  • ¼ teaspoon pure vanilla extract
  • Pinch of salt

Instructions
 

  • Preheat the oven to 350°F (177°C). Line two large baking sheets with parchment paper or silicone baking mats and set aside.
  • To make the thumbprint cookie base: In the bowl of a stand mixer fitted with the paddle attachment, or in a large mixing bowl using a handheld mixer, beat the butter until smooth. Add the brown sugar and continue mixing for 1 to 2 minutes or until well combined.
    1 cup unsalted butter,⅔ cup packed light brown sugar
  • Mix in the egg yolks, vanilla extract, and salt until fully combined.
    2 large egg yolks,1 teaspoon pure vanilla extract,¼ teaspoon salt
  • Add the flour and mix until fully combined. The mixture will be a little crumbly at first, but it will come together as you continue mixing it.
    2 ⅓ cups all-purpose flour
  • Using a 1.5 tablespoon cookie scoop (#40), scoop the cookie dough, and roll each one into a smooth ball with your hands. Roll in the granulated sugar, then place onto the prepared baking sheets.
    ¼ cup granulated sugar
  • Use the bottom of a ½-tablespoon measuring spoon to press a wide and deep indentation into the center of each dough ball, being careful not to press all the way through (there should still be a layer of dough on the bottom). A measuring teaspoon works too, but you'll need to gently work it around a little more to widen the indentation. If the dough cracks around the edges, just pinch it back together with your fingers.
  • To make the pumpkin pie filling: In a medium-sized mixing bowl, whisk together the pumpkin puree, brown sugar, egg, heavy cream, pumpkin pie spice, vanilla, and salt until smooth.
    ½ cup pumpkin puree,¼ cup packed light brown sugar,1 large egg,2 tablespoons heavy cream,½ teaspoon pumpkin pie spice,¼ teaspoon pure vanilla extract,Pinch of salt
  • Spoon the pumpkin filling into the center of each dough ball.
  • Bake for 14 to 17 minutes or until the filling looks set and the edges of the cookies are lightly golden brown.
  • Remove from the oven and allow to cool on the baking sheets for 10 minutes, then transfer to a wire rack to cool completely.

Notes

Cookies may be stored in an airtight container in the refrigerator for up to 5 days.
Freezing Instructions: Baked cookies will freeze well for up to 3 months, thaw to room temperature before serving. Cookie dough will also freeze well for up to 3 months. Thaw overnight in the refrigerator and allow to come to room temperature before shaping and filling.
Cuisine: American
Course: Dessert
Author: Danielle Rye
Did you make this recipe?Mention @livewellbakeoften on Instagram or tag #livewellbakeoften.