Caramel-Filled White Chocolate Pumpkin Cookies

24 cookies
30 min

These super soft pumpkin cookies are filled with a thumbprint of caramel and topped with white chocolate and a sprinkle of cinnamon. These basically taste like fall in cookie form!

To make these cookies, I used the thumbprint method to create an indent in the cookies after they have baked. Then I piped a generous amount of dulce de leche into the thumbprints (I use this canned dulce de leche, but you can also make your own or use caramel ice cream topping ( linked here)). If the caramel seems runny once you’ve piped it into the cookies, I recommend freezing them for a few hours to make sure that the chocolate coating doesn’t get too messy. See below for process photos!

Once you’ve filled the cookies with your caramel or dulce de leche, you can cover them with the white chocolate! Simply dip the top half of the cookies into the melted white chocolate. Lift the cookie and allow the excess chocolate to drip off. Then place it right side up and sprinkle it with cinnamon before the chocolate dries.

Caramel-Filled White Chocolate Pumpkin Cookies
Recipe details
  • 24  cookies
  • Prep time: 20 Minutes Cook time: 10 Minutes Total time: 30 min
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  • ¼ cup butter flavored shortening
  • ¼ cup unsalted butter softened
  • ½ cup granulated sugar
  • ½ cup light brown sugar packed
  • 1 teaspoon vanilla extract
  • 1 egg
  • ½ cup pumpkin puree
  • 1½ cups all-purpose flour
  • ½ teaspoon salt
  • ½ teaspoon baking soda
  • ½ teaspoon baking powder
  • 1½ teaspoons cinnamon
  • 1 teaspoon pumpkin spice
For filling and topping
  • 1 can dulce de leche ~13 ounces or 1½ cups
  • 2 cups white chocolate chips melted
To make the cookies
Preheat the oven to 350 degrees.
Using a stand mixer fitted with the paddle attachment or a hand mixer, cream the butter, shortening and sugars on high for 1-2 minutes.
Add in pumpkin puree, egg and vanilla extract. Mix until combined. Scrape down the bowl once complete.
In separate bowl, whisk dry ingredients together (flour, baking soda, baking powder, cinnamon, pumpkin pie spice and salt).
Add dry ingredients to wet ingredients in 4 different portions. Mix until combined.
Grease and line baking sheets with parchment paper or silicone baking mat.
Create 1-1 1/2 inch dough balls using a cookie dough scoop or by rolling with your hands. Place dough onto baking sheet, leaving at least 1 inch on each side of the cookies.
Bake for 10-12 minutes, or until the bottoms of the cookies are slightly browned.
Immediately after removing the cookies from the oven, use your thumb or the back of a spoon to create an indent in the middle of each cookie.
Let the cookies cool on baking sheet for 5-10 minutes, then transfer to cooling rack.
To add the dulce de leche filling
Spoon the dulce de leche or caramel topping in a piping bag or a gallon bag.
Cut an inch-wide tip in the bag and squeeze ~1 tablespoon of filling into each cookie. Lightly flatten out the tips of the dulce de leche with your finger.
Freeze the cookies for 1-2 hours for best results coating them with chocolate.
To coat the cookies in chocolate
Melt the white chocolate chips in a bowl wide enough to dip the cookies.
Pick up the cookie and dip the top into the chocolate, completely coating the top in white chocolate. Let the excess chocolate drip off of the cookie before turning it back over.
Use your finger or a spoon to swirl or spread the chocolate neatly.
Sprinkle the cookies with cinnamon before the chocolate dries.
Store in the fridge or at room temperature.
  • Chill the cookie dough before baking – this will make it easier to roll the dough or scoop it out with a cookie scoop. It will also help the cookies to remain thicker while baking.
  • Make sure that you thumbprint your cookies right when they come out of the oven, otherwise they will not be malleable enough! Use the back of a spoon to make the indent if they are too hot for your thumb.
  • Put your caramel or dulce de leche in a piping bag or gallon bag and cut a half inch tip to easily get your filling into your cookie thumbprints!
  • Once you have dipped your cookies into the melted chocolate and set them back down, feel free to use a spoon or your finger to swirl or smooth the chocolate before it dries to create a cleaner look on the cookie.
  • Sprinkle cinnamon over the tops before the chocolate dries so that it better adheres.
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