Chocolate Pie Cookies
These Chocolate Pie Cookies are the perfect combination of two classic desserts – chocolate pie and cookies! They are soft, chewy, and filled with a rich chocolate filling that will satisfy any sweet tooth.
Chocolate pie is a timeless dessert loved by many, with its flaky crust and smooth chocolate filling. On the other hand, cookies are a staple treat that can be enjoyed anytime, anywhere. So why not combine these two beloved desserts into one delicious treat?
Table of contents
❤️ Why You’ll Love This Recipe
- It combines two classic desserts into one delicious treat.
- The cookies are soft and chewy, while the chocolate filling is rich and smooth.
- It satisfies any sweet tooth craving and always pleases chocolate lovers.
🛒Ingredients
While this ingredient list may seem long to you, you don’t have to worry because most of these ingredients are pantry and staples that you most likely already have on hand so you don’t have to worry about spending a ton of money at the grocery store.
- Double Stuffed Oreo cookies
- flour
- cornstarch
- black cocoa powder
- baking soda
- baking powder
- salt
- unsalted butter
- sugar
- brown sugar
- egg
- vanilla
Filling:
- chocolate pudding mix
- milk
- heavy cream
- powdered sugar
- vanilla
- semi-sweet or dark chocolate chips
Topping:
- heavy cream
- powdered sugar
- vanilla
- Mini chocolate chips, sprinkles, chocolate curls/shavings, or chopped pieces, to decorate
See the recipe card below for quantities.
🔪 How to Make Chocolate Pie Cookies
Making these chocolate silk cookies is so easy. This list may seem a little long but we promise that they come together quickly and easily. Follow these instructions and you will have rich and fudgy cookies for your family in no time at all.
Step 1: Preheat the oven, prepare your cookie sheet, and crush the Oreos
Preheat the oven to 350 degrees. Line a baking sheet with parchment and set aside. Using a food processor, grind the Oreos until crushed.
Step 2: Combine the dry ingredients
In a medium bowl, combine the crushed Oreo pieces, flour, cornstarch, cocoa powder, baking soda, baking powder, and salt. Whisk to combine well. Set aside.
Step 3: Beat together the wet ingredients
In the bowl of a stand mixer, combine the softened butter, sugar, and brown sugar. Cream until lighter in color. Add in the egg and vanilla and combine well.
Step 4: Finish the dough
Mix in the dry ingredients into the stand mixer bowl – combine well. Stop the mixer, scrape down the sides, and mix again. The dough should be pulled away from the side of the bowl and can be pressed together to form a ball.
Step 5: Shape the dough
Divide the dough into 9 equal-sized balls and place on the prepared baking sheet. Using a flat-bottomed drinking cup, flatten the cookies into a disc shape until they are about ¾-1 inch in thickness.
Step 6: Bake the cookies
Bake in the preheated oven for 10 minutes. Immediately upon removing it from the oven, use a ¼ cup measuring cup or similar and press it into the cookie while it’s still soft. This will create the cavity needed to contain the filling. As the cookie cools it will harden, so this must be done immediately following the removal from the oven. Allow to cool completely while making the filling.
Step 7: Make the filling
In the bowl of the stand mixer, combine the chocolate pudding mix, milk, heavy cream, powdered sugar, and vanilla. Mix on medium speed for about two minutes – until the mixture is thoroughly combined and looks thick. Add in the melted chocolate and mix again. Stop the machine, scrape the sides, and mix again.
Step 8: Add the filling to a piping bag
Transfer the filling mixture to a piping bag – no tip or large round tip is fine. Set aside and wait to fill the cookies until they are baked and completely cooled.
Step 9: Make the whipped cream
In the bowl of a stand mixer, combine the heavy cream, powdered sugar, and vanilla. Whip on med/high speed for 2-3 minutes or until stiff peaks. Transfer the whipped cream to a pastry bag fitted with a large star tip. Set aside.
Step 10: Assemble the cookies
Once cool, the cookies are ready to fill. Using the piping bag for the filling, pipe a large mound in the center of each cookie. Gently tap on the counter to settle any point at the top. Pipe a small dollop of the whipped cream on top and sprinkle with desired decoration – we used chopped chocolate chips, but curls, mini chocolate chips, etc would also look great!
📝Variations
Do you want to change up this recipe and make it your own? Here are some ways that you can do that!
- Use a different type of cookie as the base, such as chocolate chip or peanut butter.
- Change the filling flavor to vanilla or caramel pudding.
- Add crushed candies or nuts on top of the whipped cream for added texture and flavor.
Do you love chocolate and pie together? If so, next time you will want to check out this Chocolate Chip Cookie Pie. It’s another great combination of these two great flavors.
🥄 Equipment
To make this recipe you will need:
- baking sheet or cookie sheet
- food processor
- electric mixer
- piping bag
- large round decorating tip
- large star tip
🥫 Storage
Store these cookies in an airtight container in the fridge for up to 3-4 days. You can also freeze these cookies before filling them and store them in an airtight container in the freezer for up to 2 months.
Serve With
These cookies pair well with a glass of milk or a cup of coffee. But, if you want to serve them with a meal we like to enjoy them after a meal of these Slow Cooker Rotel Tacos or this Slow Cooker Panera Broccoli Cheddar Soup.
💭 Tips
Here are a few tips that you can use to ensure that these cookies will turn out perfectly for you when you make them.
- Make sure that you use room temperature ingredients for your cookies. This will help them to mix more easily and come out smooth.
- Don’t overmix your dough, this can cause the texture of your cookies to be off. As soon as the ingredients are combined well you can stop mixing.
- We recommend that you use an electric mixer to make these cookies. This will help to ensure that the ingredients are mixed well and evenly.
- When filling your cookies, pipe a little extra filling than you think you might need. This will allow for any air pockets in the cookie cavity and ensure that it is filled without being too full.
- Make sure that you wait until the cookies are completely cool before you add the filling so that it doesn’t melt off.
⁉️ FAQ
Do you have questions about this chocolate pie cookies recipe? Here are the answers to the most commonly asked questions.
Yes, you can substitute store-bought whipped cream if desired.
We do not recommend freezing these cookies after they have been filled. The texture and consistency of the filling may change once thawed.
🍽 More Cookies Recipes
Do you enjoy cookies? If so, give these delicious cookies a try next time:
🧾Recipe Card
Chocolate Pie Cookies
Equipment
- Baking sheet or cookie sheet
- Food processor
- Electric mixer
- Piping bag
- large round decorating tip
- Large Star Tip
Ingredients
For the cookies:
- 10 Double Stuffed Oreo cookies
- 1 ½ cups flour
- 2 tablespoons cornstarch
- ¼ cup cocoa powder
- ½ teaspoon baking soda
- ¼ teaspoon baking powder
- ¼ teaspoon salt
- ½ cup unsalted butter softened
- ⅓ cup sugar
- ½ cup brown sugar
- 1 egg
- 1 teaspoon vanilla
For the Filling:
- 2 tablespoons chocolate pudding mix
- ½ cup milk
- 1 cup heavy cream
- ¼ cup powdered sugar
- 1 teaspoon vanilla
- 3 tablespoons semi-sweet or dark chocolate chips melted
For the Topping:
- ⅓ cup heavy cream
- 2 tablespoons powdered sugar
- ¼ teaspoon vanilla
- Mini chocolate chips sprinkles, chocolate curls/shavings or chopped pieces, to decorate
Instructions
- Preheat the oven to 350 degrees. Line a baking sheet with parchment and set aside.
- Using a food processor, grind the Oreos until crushed.
- In a medium bowl, combine the crushed Oreo pieces, flour, corn starch, cocoa powder, baking soda, baking powder and salt. Whisk to combine well. Set aside.
- In the bowl of a stand mixer, combine the softed butter, sugar and brown sugar. Cream until lighter in color.
- Add in the egg and vanilla and combine well.
- Mix in the dry ingredients into the stand mixer bowl – combine well. Stop the mixer, scrape down the sides and mix again. The dough should be pulling away from the side of the bowl and can be pressed together to form a ball.
- Divide the dough into 9 equal sized balls and place on the prepared baking sheet. Using a flat bottomed drinking cup, flatten the cookies into a disc shape until they are about ¾-1 inch in thickness.
- Bake in the preheated oven for 10 minutes. Immediately upon removing from the oven, use a ¼ cup measuring cup or similar and press it into the cookie while it’s still soft. This will create the cavity needed to contain the filling. As the cookie cools it will harden, so this must be done immediately following the removal from the oven.
- Allow to cool completely while making the filling.
Filling
- In the bowl of the stand mixer, combine the chocolate pudding mix, milk, heavy cream, powdered sugar and vanilla.
- Mix on medium speed for about two minutes – until the mixture is thoroughly combined and looks thick. Add in the melted chocolate and mix again. Stop the machine, scrape the sides and mix again.
- Transfer the filling mixture to a piping bag – no tip or large round tip is fine. Set aside and wait to fill the cookies until they are baked and completely cooled.
Whipped Topping
- In the bowl of a stand mixer, combine the heavy cream, powdered sugar and vanilla. Whip on med/high speed for 2-3 minutes or until stiff peaks.
- Transfer the whipped cream to a pastry bag fitted with a large star tip. Set aside.
Assembly
- Once cool, the cookies are ready to fill. Using the piping bag for the filling, pipe a large mound in the center of each cookie. Gently tap on the counter to settle any point in the top. Pipe a small dollop of the whipped cream on top and sprinkle with desired decoration – we used chopped chocolate chips, but curls, mini chocolate chips, etc would also look great!
