Funfetti Oreo Stuffed Cookie Cups

If you love chocolate chip cookies, and oreos, and frosting, and anything with sprinkles then this is the dessert for you. This is like the answer to what should I have for dessert. How about just about everything all rolled into one?  Why decide? When someone asks you to bring dessert- bring them all..in one with these Funfetti Oreo Stuffed Cookie Cups

 So raise your hand if you agree with me. Sometimes you want a chocolate chip cookie. Sometimes you want an Oreo. Sometimes you want a cupcake and sprinkles and pile of buttercream frosting. Was your hand up every single time? Me too. And then sometimes you get this crazy idea to put all of them together. Because you want them all. All at once. With no judgment. So…Oreo meet cookie meet cupcake.

This was just one of those ideas that kind of took on a life of its own.

It started with lets make a funfetti chocolate chip cookie. Let’s stuff them into a cupcake pan!

Ooh, I know let’s stuff an Oreo cookie inside! Because how could that be bad? Oh by the way it isn’t.

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Baking Tools You Need To Make These Oreo Stuffed Cookie Cupcakes:

• Cupcake Pans –  My favorite cupcake pans are these ones from Wilton and these ones from Chicago Metallic.
• Large Piping Tips – To get those professional looking frosting swirls you need large cupcake tips. You could get a set like this one, or individual cupcake tips from Ateco (which are the ones I own).
• Piping bags –  You can use reusable piping bags or disposable piping bags (which is my preference). I prefer to use the 18-inch bags so I do not have to refill as often!

How To Make These Oreo Stuffed Cookie Cups

1. Whisk flour and baking soda together in a medium bowl and set aside.

2. Melt 14 tablespoons butter in a saucepan over medium heat until melted (could also be down in a bowl in the microwave- just be careful and cover the bowl so the butter doesn’t splatter).

3. Transfer melted butter to a mixing bowl. Add brown sugar, granulated sugar, salt, and vanilla to the mixing bowl. Whisk until incorporated. Add the egg and egg yolk; whisk until the mixture is smooth with no sugar lumps remaining, about 30 seconds. Let mixture stand for 3 minutes, then whisk for 30 seconds. Repeat until the mixture is thick, smooth, and shiny.

4. Using rubber spatula, stir in flour mixture just until incorporated (about 1 minute). Stir in sprinkles and chocolate chips. Give dough one final stir to ensure all flour is incorporated.

5. Chill dough for 1-2 hours.

6. When ready, preheat oven to 375 degrees. Grease a muffin tin or use cupcake liners to ensure they don’t stick. Scoop 1 tablespoon of dough and press into the bottom of a cupcake well covering the bottom. Top with an Oreo cookie. Scoop a second tablespoon of dough and press on top, being sure to cover up the Oreo. Repeat with the remaining dough and cookies.

7. Bake for 12-15 minutes until the cookies are golden brown and still puffy and edges have begun to set. Transfer cupcake pan to a wire rack; allow cookies to cool before removing from the cupcake pan. If the edges are slightly stuck, carefully run a knife along the edge to loose. Place the cookie cupcakes on a wire rack to fully cool before adding the frosting on top.

8. To make the frosting: In a clean and dry stand mixer bowl with paddle attachment, add the butter and cream until smooth and fluffy about 3 minutes. Add in the powdered sugar 1/2 cup at a time, full incorporating before adding more. Once all the powdered sugar has been added, stop mixer and add in the heavy cream and vanilla extract. Start the mixer slowly and after about 1 minute increase speed to medium and mix for 8 minutes until light and fluffy.

9.  To assemble the cupcakes: Using the Ateco tip and piping bag, fill with the vanilla buttercream and swirl the frosting on top of each cupcake. If desired, add more sprinkles on top!

10. Can be stored in the refrigerator for up to 2 days- allow to come to room temperature again before serving due to the high amount of butter in the frosting. You could freeze the cookie cupcakes as well. Freeze before adding the frosting in a airtight container or zip-loc bag. Add frosting once cookies have defrosted.

And then seriously, why stop there? Let’s just go ahead and swirl on some of the best vanilla buttercream frosting ever. If you want to master making buttercream, then be sure to read the Ultimate Guide To Making The Best Buttercream Icing Ever. 

Oh welcome to the world Oreo Stuffed Funfetti Chocolate Chip Cookie Dough Cups.

I am absolutely in love with these cupcakes…err I mean, cookies? Oh whatever you want to call them.

MAKE. THEM. NOW.

Tips On Making These Cookie Cups

• Measure your flour accurately. I recommend using a kitchen scale for this. Or be sure to fluff up your flour then spoon into your dry measuring cup and level with a flat edge. For a complete tutorial, read this post.
• Chilling your cookie dough is a must for flavor and texture. You can make this dough ahead of time, up to 24 hours, to make this recipe even easier.
• When adding the flour to the mixture, be sure to not overmix. I like to leave a streak of flour in the bowl to ensure I don’t overmix.
• To shape these cookie cups, you want to scoop 1 ball of dough into a greased muffin pan or one lined with cupcake liners and flatten it down a bit. Top with an Oreo cookie, and then cover it up with another 1-inch ball of cookie dough.
• Be sure to not frost these cookie cups until they are completely cooled.
• You can make these ahead of time. Simply freeze unfrosted, and then thaw at room temperature and frost.

Let’s break down these Oreo stuffed cookie cups recipe a bit…

• Ease of Recipe: They start with a classic chocolate chip cookie. Now I’ve made what I called the best chocolate chip cookie before- aka The New York Times Chocolate Chip Cookie. However, this one is simpler because it uses all purpose flour. No bread flour or cake flour needed. Just good ol’ all purpose! Also, I only chilled the cookie dough for about 2 hours not a whole 24 hours #aintnobodygottimeforthat – so that means this dough comes together a lot faster! Which simply means cookies in my mouth faster 🙂
• Flavor: I used a mix of brown sugar and white sugar for these cookies. I love the flavor and the chewiness that the brown sugar gives to the cookies and the crispiness that white sugar lends. I used more brown sugar than white sugar- double in fact- and I think its what help makes these cookies their awesome flavor.
• Fun, fun, fun– So yea, I stuffed the cookies with an Oreo, and loaded the dough with sprinkles, baked them in a cupcake pan and topped them with buttercream. Which translates to me as cookie fun times three. To make these, I used my go to cupcake pan which I love, love, love. No need to grease the cupcake wells because of the butter in the dough. To get the Oreo inside, simply press about 1-inch ball of cookie dough in the bottom of each. Plop (fancy cooking term for set Oreo on top) the Oreo and then top with another 1-inch ball of cookie on top pressing around the edges.  You will bake these as you would your normal cookies. Allow your cookies to cool a bit before trying to take them out of the cupcake pan otherwise the soft cookies might fall apart on you. (This happened to me- I called that my test cookie #lifeofablogger) 🙂  And just like you would for a normal cupcake- allow to cool completely before topping with the frosting! I used this Ateco tip and piping bags in case you’re curious!

Why This Recipe Works: Well besides the obvious that there’s an Oreo cookie inside a chocolate chip cookie. And topped with fluffy creamy buttercream. It’s the cookie that has to be amazing. And it is. The cookie is made with more brown sugar than white sugar so it results in a softer chewier cookie. The addition of an egg yolk adds extra fat and protein to the dough, so it will help to also soften the cookie and add more chew. This cookie recipe classically uses baking soda which helps to create that golden brown color and helps give it that toasty caramel color. 

The Science Behind The Sweets: What Is The Difference Between Baking Powder and Baking Soda?

Ok this could be an entire post on its own so this is the quick version.  Baking Powder and Baking Soda are both leavening agents- meaning they help give your baked goods rise. Baking Soda, or bicarbonate of soda, is a base which means it needs an acid to react with (like vinegar or lemon juice). When the two mix, carbon dioxide gas is produced which is what produces the lift. Baking Powder is actually a combination of baking soda, cream of tartar, and usually cornstarch to keep them seperate and reacting on their own. Baking powder is double-acting meaning it reacts first together when liquid is added, and second when heat is applied. Although the main reason to add these leavening agents is to help your desserts, well, leaven. They also have a second role which is to add flavor and color.  

So if you can’t decide between chocolate chip cookie, Oreos, or a cupcake. Then don’t! And seriously, why should you have to?

If you like this recipe let me know and leave me a comment! And would you do me a favor and  Pin This Recipe For Later?

Happy baking!