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Oreo-Stuffed Double Chocolate Cookie Cups

written by Ashley Fehr

Updated May 17, 2024

5 from 3 votes
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These Oreo-Stuffed Double Chocolate Cookie Cups are crisp on the edges, chewy in the middle and absolutely LOADED with chocolate! Frosted or unfrosted — you decide!

oreo cookie cups stacked with top cookies cut in half to reveal oreo inside

This recipe is brought to you by my maternity pants.

Because they are way too stretchy and enable me to create and eat things like this.

In all fairness, I made these to bring to my coworkers at the high school when I went to bring the baby for a visit. So I guess, knowing that I wouldn’t actually be left to eat these by myself, I went a little overboard.

I was trying to think of something to bake to bring to the school, because I have a bit of a reputation.

Now, I’m not saying that I am some sort of baking queen and everything I make is amazing, but I’ve experimented on them quite a bit in the past so they’ve gotten a little used to me bringing goodies.

It’d be a little awkward to go empty-handed.

And plus, I’ll never get out of these darn maternity pants if I don’t share.

oreo chocolate cookie cups in bowl with some whole and some halved to reveal oreo inside

So I started scanning my Bars, Square and Cookies board on Pinterest, thinking maybe I would try another blogger’s recipe or make something that was already on the blog so that I could just relax and bake, and not worry about the photography and all that jazz.

And I saw some oreo-stuffed chocolate chip cookies, and I thought, “I should make those.”

And then I thought, “more chocolate.”

So obviously, I made some double chocolate cookies and stuffed them with an Oreo. And then I remembered this Oreo filling frosting and thought I had better make some to smother on top. And top that with crushed Oreos.

I know not everyone is into frosting (and to be honest, the older I get, the less I enjoy the overly sweet!), so that part is up to you 😉

frosted oreo cookie cups on marble with piece of oreo cookie on top

And, to be honest, they don’t need any frosting. And if you’re someone who doesn’t like things overly sweet, unfrosted is the way to go. But if you’re looking to get a little crazy…. go all out.

Love Oreo treats? Try these next:

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Oreo-Stuffed Double Chocolate Cookie Cups

written by Ashley Fehr

These Oreo-Stuffed Double Chocolate Cookie Cups are crisp on the edges, chewy in the middle and absolutely LOADED with chocolate! Frosted or unfrosted — you decide!
oreo chocolate cookie cups in bowl
5 from 3 votes
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Prep Time: 40 minutes
Cook Time: 15 minutes
Total Time: 55 minutes
Course: Dessert
Cuisine: American
Servings: 24 cookie cups
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Ingredients 

Cookies:

  • 1 cups butter
  • 2 cups sugar
  • 1 tsp vanilla
  • 2 eggs
  • 2 cups flour, I used half whole wheat
  • 1 tsp baking soda
  • 1 tsp salt
  • 2/3 cup cocoa
  • 1 cup mini chocolate chips
  • 24 Oreo cookies

Frosting

  • 1/2 cup white chocolate, chopped
  • 1/4 cup milk
  • 1/2 cup butter
  • 1 tsp vanilla
  • 3 cups powdered icing sugar
  • 3-4 Oreos, crushed
US Customary – Metric
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Instructions 

Cookies

  • Preheat oven to 350 degrees.
  • In the bowl of a stand mixer, beat butter and sugar until light and fluffy. Add vanilla and eggs and beat until smooth.
  • Add flour, baking soda, salt and cocoa and beat until combined. Add chocolate chips and beat on low until combined. If cookie dough is still a bit sticky, refrigerate for 1 hour.
  • Prepare 24 muffin cups: use a regular muffin pan, well-greased or use silicone muffin cups ungreased (a dark pan will result in crispier edges, a silicone pan will result in softer edges)
  • Drop a rounded teaspoon of cookie dough in each muffin cup. Press down with your fingers and work dough up the edges just slightly. Place one Oreo in the middle, pressing down gently. Scoop another rounded teaspoon of dough and flatten it into a circle the size of the muffin cup. Place on top of each Oreo and press down the sides gently to surround the Oreo.
  • Bake for 12-14 minutes until centers appear set. Set aside to cool.

Frosting (optional)

  • In a small bowl, melt white chocolate and milk in the microwave in 30 second intervals, stirring in between. Set aside to cool slightly (15-20 minutes)
  • With an electric mixer, beat butter until smooth. Add cooled chocolate mixture and vanilla and beat until combined.
  • Add powdered sugar, one cup at a time, beating until combined after each addition. Beat on high 2-3 minutes until light and fluffy.
  • Frost cooled cookie cups and garnish as desired.

Nutrition

Calories: 348cal, Carbohydrates: 50g, Protein: 3g, Fat: 15g, Saturated Fat: 9g, Cholesterol: 42mg, Sodium: 276mg, Potassium: 88mg, Fiber: 1g, Sugar: 37g, Vitamin A: 355IU, Vitamin C: 0.1mg, Calcium: 27mg, Iron: 2mg

Nutrition information is automatically calculated, so should only be used as an approximation.

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Meet Ashley

My name is Ashley Fehr and I love creating easy meals my family loves. I also like to do things my way, which means improvising and breaking the rules when necessary. Here you will find creative twists on old favorites and some of my favorite family recipes, passed down from generations!

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Comments

  1. Maddison says

    Does anyone know if these can be microwaved to make warm after they have cooled, maybe like a day later or something if I wanted one warm?

    Reply

  3. Joseph says

    Hi Ashley, I’m making these a head of time, tonight For an event tomorrow. Should I refrigerate or freeze these overnight?

    Love this recipe and I cannot wait to make it

    Reply

  4. Susan says

    Ashley,

    These look very delicious! Plan on making these in the next couple of months.

    I do have a question. What type of flour should be used? All Purpose? It would be nice, if recipes had the type of flour that the recipes require, along with the Brands which people used to make them.

    My son had just gotten his own place & he likes Oreo’s. I’m going to send him the link to your website & recipe.

    Thanks for the Chocolate Recipes!

    Reply

  5. Mary says

    I’m not sure if I hit send so I am asking Again! Can you freeze this Oreo cookie cup
    and if so how do they hold up?

    Reply
5 from 3 votes (1 rating without comment)

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