These Keto Dulce de Leche Pumpkin Cookie Cups are a decadent convergence of a chewy pumpkin spiced cookie with an oh-so-smooth dulce de leche filling. They also happen to be sugar free. That’s great, but I’d gladly eat about a million of these even if they weren’t. Definitely add these to your holiday baking list!
Just about anytime I think about little filled cookies (like the caramel tassies that are among my all time favorites), they always seem like too much effort. Truth be told, I have that feeling about many of the bite-size foods that I dearly love. However, the reality is that if you plan out what you need to do for them (and read all the instructions before you start), you can usually streamline the process dramatically.
With that mindset, keep reading to see how to put these devilishly good cookie cups together.
The pumpkin cookie cups were inspired by these Keto Pumpkin Cookies from All Day I Dream About Food.
The filling uses this Sugar Free Dulce de Leche also from All Day I Dream About Food.
What You Need to Make Keto Dulce de Leche Pumpkin Cookie Cups
Equipment
- Stand Mixer – Or Large Mixing Bowl and Hand Mixer
- Measuring Cups
- Measuring Spoons
- 2 Mini Muffin Pans (Preferably Silicone)
- Nonstick Cooking Spray
- 2 Rimmed Baking Sheets – Or other tray that fits in your fridge
- Aluminum Foil
- Medium Saucepan
- Whisk
- Rubber Scraper
Ingredients
- For the Pumpkin Cookie Cups:
- Unsalted Butter
- Swerve Brown – You could also use another brown sugar substitute like Sukrin Gold.
- Granulated Erythritol
- Egg – I use jumbo eggs.
- Pumpkin Purée
- Vanilla Extract
- Molasses – You can skip it if you really want to, but given that it is 2 teaspoons spread across 48 cookie cups, the carb count impact is minimal. It adds about 0.19 grams of carbs per cookie cup.
- Almond Flour – Yes, really do sift it.
- Gelatin
- Ground Ginger
- Ground Cinnamon
- Baking Soda – Yep, I really mean “baking soda” not “baking powder” in this case.
- Kosher Salt
- Ground Cloves
- For the Filling:
- Heavy Cream
- Allulose – Don’t try to substitute erythritol for this part of the recipe. It will recrystallize as it cools, which isn’t the texture you’re going for in the filling.
- Swerve Brown – See above.
Getting Started with Making Keto Dulce de Leche Pumpkin Cookie Cups
Making the Pumpkin Cookie Cups
First we need to make the pumpkin cookie cups so that they have time to cool completely and firm up a bit before we fill them.
Beating the Wet Ingredients
You’ll start by using a stand mixer (or a large mixing bowl and hand mixer) to beat together ½ cup of Unsalted Butter (softened), ½ cup of Swerve Brown, and ½ cup of Granulated Erythritol for about 2 minutes or until fluffy. Then you beat in 1 Egg, ¼ cup Pumpkin Purée, ½ teaspoon Vanilla Extract, and 2 teaspoons Molasses.
Combing the Dry Ingredients
Next, you’ll use a medium bowl to thoroughly combine the dry ingredients–2.25 cups Almond Flour (sifted), 2 tablespoons Gelatin, 1 tablespoon Ground Ginger, 1 teaspoon Ground Cinnamon, ½ teaspoon Baking Soda, ¼ teaspoon Kosher Salt, ¼ teaspoon Ground Cloves.
Putting Everything Together
Then you need to add the dry ingredients into the wet ingredients, about a quarter at a time. You’ll want to beat the batter until it forms a dough.
At this point, you can preheat the oven to 325°F and grease a mini muffin pan.
You need to roll the cookie dough into 1-inch balls. Then you can set each ball into a mini muffin well and gently press it flat with your fingers. After that, if you have one, you can use a tart press to make an indentation in the center of each cookie round so that the dough comes up the sides of the mini muffin well.
Baking
Start the baking process (yes, it’s a process) by baking the cookies cups at 325°F for 5 minutes. Then you need to remove them from the oven, press the indentations again with the mold.
After that, you can return them to the oven for 7 more minutes, then remove from them again, and press them again with the tart press. Now, you return them to the oven for up to 5 more minutes. The edges will just start to turn golden. Remove them from the oven one last time and press again.
You should then let them cool in the pan for at least 20 minutes. Remove the cookie cups from the pan and cool completely before filling.
Making the Sugar Free Dulce de Leche
(If in doubt, refer to the original instructions here on All Day I Dream About Food.)
We’ll start this part of the process by combining 3 cups of Heavy Cream, ⅔ cup of Allulose, and 6 tablespoons of Swerve Brown in a medium saucepan. We need to bring the mixture to a boil and then reduce the heat to a simmer. From there, we’ll let it continue to cook, stirring continuously until it has thickened and reduced by about 25%. It should be a fairly dark caramel color.
Then we need to remove it from heat and allow it to cool for about 5 minutes.
Assembling the Cookie Cups with Filling
As the final stage, we’ll put everything together. But first, you need to make space in your fridge for a tray so that you can place all of the cookies in a single layer. I suggest that you line the tray with aluminum foil for easier cleanup.
Next, we’ll set out the cookie cups on that tray. Now you can go ahead and fill each cookie cup with the sugar free dulce de leche while it is still a bit warm and easily pourable. (If you wait too long, it will set up and be harder to work with.) You want to fill each cookie cup to the top.
Once you’re done, you can place the filled cookie cups in the fridge and allow them to chill and set for at least 2 hours. This gives them plenty of time to solidify.
Serve them at room temperature or chilled. After that, you can store them in an airtight container in the fridge with a sheet of waxed paper between layers of cookie cups.
Related Recipes
If you’re looking for something pumpkin-y for dessert, you might want to try my Low Carb Pumpkin Bread Pudding.
Maybe you’re interested in some other cookies?
If you’re wonder what else to serve with these Keto Dulce de Leche Pumpkin Cookie Cups, take a look at my Friendsgiving Food Ideas for some suggestions.
Keto Dulce de Leche Pumpkin Cookie Cups
Ingredients
For the Cookie Cups:
- ½ cup Unsalted Butter Softened
- ½ cup Swerve Brown Or another brown sugar substitute like Sukrin Gold.
- ½ cup Granulated Erythritol
- 1 Egg I use jumbo eggs. Room Temperature
- ¼ cup Pumpkin Purée
- ½ teaspoon Vanilla Extract
- 2 teaspoon Molasses
- 2 ¼ cups Almond Flour Sifted
- 2 tablespoon Gelatin
- 1 tablespoon Ground Ginger
- 1 teaspoon Ground Cinnamon
- ½ teaspoon Baking Soda
- ¼ teaspoon Kosher Salt
- ¼ teaspoon Ground Cloves
For the Filling:
- 3 cups Heavy Cream
- ⅔ cup Allulose
- 6 tablespoons Swerve Brown
Instructions
To Make the Cookie Cups:
- Using a stand mixer or a large mixing bowl and hand mixer, beat ½ cup Unsalted Butter (softened), 1/2 cup Swerve Brown, and 1/2 cup Granulated Erythritol for about 2 minutes or until fluffy. Then beat in 1 Egg, ¼ cup Pumpkin Purée, ½ teaspoon Vanilla Extract, and 2 teaspoon Molasses.½ cup Unsalted Butter, 1/2 cup Swerve Brown, 1/2 cup Granulated Erythritol, 1 Egg, ¼ cup Pumpkin Purée, ½ teaspoon Vanilla Extract, 2 teaspoon Molasses
- In a medium bowl, combine the dry ingredients–2 ¼ cups Almond Flour (sifted), 2 tablespoon Gelatin, 1 tablespoon Ground Ginger, 1 teaspoon Ground Cinnamon, ½ teaspoon Baking Soda, ¼ teaspoon Kosher Salt, ¼ teaspoon Ground Cloves. Whisk to combine.2 ¼ cups Almond Flour, 2 tablespoon Gelatin, 1 tablespoon Ground Ginger, 1 teaspoon Ground Cinnamon, ½ teaspoon Baking Soda, ¼ teaspoon Kosher Salt, ¼ teaspoon Ground Cloves
- Add the dry ingredients to the wet ingredients about a quarter at a time. Beat until it forms a dough.
- Preheat the oven to 325°F and grease a mini muffin pan.
- Roll cookies into 1-inch balls, set each ball into a mini muffin well and gently press it flat with your fingers.
- Use a tart press to make an indentation in the center of each cookie round so that the dough comes up the sides of the mini muffin well.
- Bake for 5 minutes, remove from the oven, press the indentations again with the mold. Return to the oven for 7 more minutes, remove from the oven, press again. Return to the oven for up to 5 more minutes. The edges will just start to turn golden. Remove from the oven, press again.
- Cool in the pan for at least 20 minutes. Remove from the pan and cool completely before filling.
To Make the Sugar Free Dulce de Leche Filling (See link to original recipe in the Notes):
- Combine 3 cups Heavy Cream, ⅔ cup Allulose, and 6 tablespoons Swerve Brown in a medium saucepan.3 cups Heavy Cream, ⅔ cup Allulose, 6 tablespoons Swerve Brown
- Bring the mixture to a boil. Then reduce the heat to a simmer and cook, stirring continuously until thickened and reduced by about 25%. It should be a fairly dark caramel color.
- Remove from heat and allow to cool for about 5 minutes.
To Assemble:
- Make space in your fridge for a tray so that you can place all of the cookies in a single layer. Line the tray with aluminum foil for easier cleanup.
- Set out the cookie cups on that tray. Fill each cookie cup with the sugar free dulce de leche while it is still a bit warm and easily pourable. (If you wait too long, it will set up and be harder to work with.) Fill each to the top.
- Place the filled cookie cups in the fridge and allow them to chill and set for at least 2 hours. This gives them plenty of time to solidify.
- Serve at room temperature or chilled. After that you can store them in an airtight container in the fridge with a sheet of waxed paper between layers of cookie cups.
Equipment
- Stand Mixer Or Large Mixing Bowl and Hand Mixer
- Measuring Cups
- Measuring Spoons
- 2 Mini Muffin Pans Preferably Silicone
- Nonstick Cooking Spray
- 2 Rimmed Baking Sheets Or other tray that fits in your fridge
- Aluminum Foil
- Whisk
Notes
- For the Sugar Free Dulce de Leche, I made it exactly as instructed here on All Day I Dream About Food:
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