Cookie Cup Cupcakes

Cookie Cup Cupcakes are a crisp chocolate chip cookie surrounding a moist chocolate cupcake…need I say more?

A Cookie Cupcake. Need I say more?

A classic chocolate chip cookie dough surrounding a rich chocolate cupcake makes these Cookie Cup Cupcakes one of the most incredible things you will ever bite into. The outside is crispy with a slight chew and lots of melting chips of chocolate. Inside you’ll find a rich, moist chocolate cake center, all topped with fluffy chocolate frosting. Your mind will be blown by this cookie cupcake combination. It’s a game-changer, for sure!

Double Whammy!

I love a good two-in-one treat. This cookie cupcake reminds me of the brookie (brownie plus cookie). From a family-favorite brookie pie, or the super decadent peanut butter cup stuffed brookie, the combination is so hard to resist. And as you can see from the pic above, this cookie cupcake creation I’m sharing with you is out of this world AMAZING!!! A crisp chocolate chip cookie surrounding a moist chocolate cupcake…need I say more?

They’re so worth the extra effort to create something this great! You just have to bake them to experience the amazingness for yourself. One bite in and you’ll be blown away!

Ingredients and Supplies

(see recipe card at the bottom of this post for measurements and details. To learn more about specific baking ingredients and how they function in baking recipes, reference my Complete Guide to Baking Ingredients)

Ingredients:

• Unsalted butter (softened): gives the cookie dough its rich flavor, tender texture, and helps create soft, chewy cookie cups. Salted butter works too—just reduce the added salt in the dough to 1/2 teaspoon.
• Granulated sugar: adds sweetness and helps the cookie dough spread and brown beautifully.
• Light brown sugar: adds moisture, chewiness, and a subtle caramel flavor. Dark brown sugar can be used for a richer molasses flavor, or use all granulated sugar if needed, though the cookie will be less chewy.
• Large eggs: bind the dough together while adding richness and structure.
• Vanilla extract: enhances all the sweet, chocolatey flavors in the cookie dough.
• All-purpose flour: provides the structure that holds the cookie cups together.
• Baking soda: helps the cookie dough rise slightly while creating a soft, chewy texture.
• Kosher salt: balances the sweetness and enhances the chocolate and vanilla flavors. Table salt will actually pack a saltier punch than Kosher salt so if you only have table salt, adjust accordingly.
• Semi-sweet chocolate chips: add pockets of melty chocolate throughout every bite. Milk chocolate, dark chocolate, white chocolate, chopped chocolate, or peanut butter chips all work as well.

Cupcake Filling:

• Unsalted butter: adds richness and helps keep the cupcake filling moist and tender.
• Semi-sweet chocolate chips: when melted, provide rich chocolate flavor and create a fudgy texture.
• All-purpose flour: gives the cupcake filling structure while keeping it soft.
• Baking powder: helps the cupcake filling rise into a light, tender cake.
• Unsweetened cocoa powder: deepens the chocolate flavor without adding extra sweetness. Dutch-processed cocoa may be used for a smoother, darker chocolate flavor.
• Granulated sugar: sweetens the cupcake filling while helping create a soft crumb.
• Large egg: provides structure, moisture, and richness to the cupcake batter.
• Milk: adds moisture and creates a smooth, tender batter. Whole or 2% milk work best.
• Vanilla extract: rounds out and enhances the chocolate flavor.

Chocolate Frosting:

• Unsalted butter (softened): creates a rich, creamy frosting that’s perfect for piping. Salted butter works well—simply omit the kosher salt.
• Powdered sugar: sweetens and thickens the frosting while keeping it silky smooth. Sift first to avoid lumps.
• Unsweetened cocoa powder: gives the frosting its rich chocolate flavor. Dutch-process cocoa powder can be used for a darker color and smoother flavor.
• Kosher salt: balances the sweetness and intensifies the chocolate flavor.
• Vanilla extract: enhances the chocolate flavor and adds warmth to the frosting.
• Milk: thins the frosting to the perfect spreading or piping consistency. Whole or 2% works best and heavy cream would make for an even richer frosting.
• Chocolate chips (for garnishing): adds a fun finishing touch and a little extra chocolate in every bite.

Supplies:

• Electric mixer (or large mixing bowl with a hand mixer)
• Mixing bowls
• Small microwavable bowl
• 12-cup cupcake pan
• Baking cup liners
• Non-stick cooking spray
• Wire cooling rack

How to Make Cookie Cup Cupcakes

• Cookie Dough: In the bowl of an electric mixer, beat the butter and sugars until creamy.
• Add the eggs, one at a time, beating until well combined.
• Beat in the vanilla.

• In a separate bowl, whisk together the flour, baking soda, and salt.
• Add to the wet ingredients and beat on low until just combined.

• Stir in the chocolate chips.
• Scoop cookie dough into 12 large (about 2 tablespoon-sized) & 12 small (about 2 teaspoon-sized) balls on a parchment lined baking sheet.
• Place in the refrigerator for at least one hour so cookie dough is firm enough to mold into the cupcake pan.
• Cupcake Filling: Add butter and chocolate to a small microwavable bowl.

• Melt the butter and chocolate until just melted, about 60-90 seconds, stirring every 30 seconds. Set aside to cool slightly.
• In a large bowl, whisk together the flour, baking powder, cocoa, and sugar.
• In a separate small bowl, whisk together the egg, milk and vanilla.

• Add the milk mixture to the flour mixture and stir until just combined.
• Stir in the melted chocolate.

• Preheat the oven to 350°F. Line a 12-cup cupcake pan with baking cup liners and spray with non-stick cooking spray.
• Once the cookie dough balls are cold, remove from refrigerator. Place a large ball of dough in one of the prepared cupcake liners and press into the bottom and up the sides so the dough is sticking up just above the liner.
• Fill the cookie dough cup completely with cupcake batter. Flatten one of the small balls of cookie dough in the palm of your hands and place it on top of the cupcake batter, pressing around the edges to seal the cupcake batter in. Repeat with remaining cookie dough balls and cupcake batter.
• Bake for 25-30 minutes or until the cookie tops are starting to turn golden brown and a toothpick inserted in the center comes out clean or with a few moist crumbs.

• Let cool in pan 10 minutes before removing to a wire rack to cool completely.
• Chocolate Frosting: In the bowl of an electric mixer fitted with the whisk attachment (or large mixing bowl with a hand mixer), beat the softened butter until smooth and creamy.
• Add the powdered sugar, cocoa powder, and salt. Mix on low speed until combined.
• Add the vanilla extract and 4 tablespoons milk. Beat for 2 to 3 minutes until fluffy and smooth. Add more milk, 1 tablespoon at a time.

• Beat until the frosting reaches your desired consistency.

• Once cupcakes are cooled, pipe frosting on the top of each one and sprinkle with a few chocolate chips, if desired.

Storage

Store leftover frosted Cookie Cup Cupcakes in an airtight container at room temperature for up to 2 days or in the refrigerator for up to 5 days. If refrigerated, let them sit at room temperature for 20–30 minutes before serving so the cookie cup softens and the frosting becomes creamy again.

If you’d like to make them ahead, bake the cookie cup cupcakes as directed and let them cool completely. Store the unfrosted cupcakes in an airtight container at room temperature for up to 2 days or refrigerate for up to 5 days. Prepare the frosting when you’re ready to serve, or make it ahead and refrigerate it separately in an airtight container. Let the frosting come to room temperature and give it a quick whip before frosting the cupcakes.

For longer storage, freeze the completely cooled, unfrosted cupcakes in a freezer-safe container or zip-top bag for up to 3 months. Thaw overnight in the refrigerator or at room temperature for a few hours, then frost and garnish just before serving for the freshest taste and texture.

If you make my Cookie Cup Cupcakes and post a pic to social, be sure to tag me on Instagram @thebakermama so I can see! If you’re on Facebook, be sure to join my Friends of The BakerMama group to connect and share all the fun and yummy recipes of mine that you make! 😍 I just love seeing how inspired and creative y’all get with the recipes and ideas I share. Enjoy!

xoxo,

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