Introduction

These Chocolate Pie Cookies combine rich, fudgy cookie bases with a smooth, creamy chocolate filling and a dollop of whipped cream on top. Perfectly balanced in texture and flavor, they offer a delightful twist on classic cookies that your family and friends will love.

A stack of four thick, round chocolate cookies is shown on a white marbled surface. Each cookie is dark brown with a slightly cracked, textured exterior. Between the cookies are smooth layers of light brown chocolate cream and white cream. The top cookie is broken in half and placed upright, showing the inside layers—dark cookie, smooth chocolate cream, and topped with a white cream layer sprinkled with small dark chocolate shavings. The background is softly blurred with more cookies and a glass jar of milk. Photo taken with an iphone --ar 4:5 --v 7

Ingredients

½ cup salted butter (softened)
1 cup brown sugar
1 large egg
1 teaspoon vanilla extract
1 ¼ cups all-purpose flour
¼ cup Dutch process cocoa powder
1 teaspoon baking powder
½ cup instant chocolate pudding mix
1 cup whole milk
¼ cup heavy cream (for pudding)
1 cup heavy cream (for whipping)
1 teaspoon vanilla extract (for whipping cream)

Instructions

Step 1: In a large mixing bowl, combine the softened butter and brown sugar. Use an electric hand mixer to whisk together for 3 minutes until the mixture is smooth and creamy.
Step 2: Add the egg and 1 teaspoon vanilla extract to the bowl. Mix again for a few minutes until the egg is fully incorporated and the mixture is smooth.
Step 3: Gradually whisk in the flour, Dutch process cocoa powder, and baking powder. Reduce your mixer’s speed to avoid splattering. Make sure the dough has no pockets of dry ingredients. Cover with plastic wrap and chill in the refrigerator for 20 minutes. Meanwhile, preheat your oven to 350°F (175°C).
Step 4: While the dough chills, whisk together the whole milk and instant chocolate pudding mix until smooth. Stir in ¼ cup heavy cream, then cover the pudding with plastic wrap and place it in the freezer to set.
Step 5: Scoop 1 ½ tablespoon-sized balls of cookie dough and roll them gently in your hands. Place the dough balls onto a baking sheet, spacing them at least 1 ½ inches apart. Bake for 12 minutes.
Step 6: Immediately after removing from the oven, press a small indent in the center of each cookie using a small dish or the back of a spoon to create a well for the filling. Let cookies cool completely to room temperature.
Step 7: Beat 1 cup heavy cream and 1 teaspoon vanilla extract together until stiff peaks form, about 3 to 5 minutes. Fill each cookie indent with a spoonful of the chilled pudding mixture, then top with a dollop of the whipped cream.
Step 8: Serve and enjoy these luscious chocolate pie cookies fresh for the best taste and texture.

Tips & Variations

For a richer flavor, use high-quality Dutch process cocoa powder and fresh vanilla extract.
To make these cookies nut-free, ensure your pudding mix and other ingredients do not contain any nut traces.
Try adding a pinch of espresso powder to the dough to deepen the chocolate flavor.
For a festive touch, sprinkle a little chocolate shavings or cocoa powder over the whipped cream topping.

Storage

Store the filled cookies in an airtight container in the refrigerator for up to 3 days. Because of the whipped cream and pudding filling, these cookies are best enjoyed fresh. If needed, allow refrigerated cookies to come to room temperature for a few minutes before serving. Do not freeze filled cookies, as the texture of the filling will suffer.

How to Serve

The image shows a white plate with a thin dark rim filled with nine round chocolate cookies. Each cookie has three layers: the bottom is a rough, cracked dark brown cookie base; the middle is a smooth, glossy lighter brown chocolate filling; the top is a swirl of white cream with slightly pointed peaks, decorated with small dark brown chocolate shavings. The plate sits on a white marbled surface with scattered dark chocolate shavings and chocolate pieces nearby. In the background, there is a light soft orange and white striped cloth and a white container. photo taken with an iphone --ar 4:5 --v 7

Serve this delicious recipe with your favorite sides.

FAQs

Can I make the cookie dough ahead of time?

Yes, the cookie dough can be made and refrigerated for up to 24 hours before baking. Be sure to cover it tightly with plastic wrap to prevent drying out.

What can I substitute for instant chocolate pudding mix?

If you don’t have instant pudding mix, you can make a homemade chocolate pudding or use a thick chocolate ganache as a filling, but the texture and firmness may vary slightly from the original recipe.