The Recipe Rebel / Desserts
written by Ashley Fehr
5 from 3 votes
Prep Time 40 minutes mins
Total Time 55 minutes mins
Servings 24 cookie cups
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Last updated on June 9, 2020
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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!
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.
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 😉
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.
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Pin this recipe to your favorite boardOreo-Stuffed Double Chocolate Cookie Cups
written by Ashley Fehr
5 from 3 votes
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!
Save
ReviewPrep Time 40 minutes mins
Cook Time 15 minutes mins
Total Time 55 minutes mins
Cuisine American
Course Dessert
Servings 24 cookie cups
Calories 348cal
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
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 Information
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
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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!
Read More
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Reader Interactions
Comments
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
Ashley Fehr says
Thanks! No need to refrigerate or freeze unless they are frosted, they should be great!
Reply
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
Ashley Fehr says
Hi Susan! You’re right, that would be helpful! Unless otherwise stated, I always use all-purpose flour. I hope he enjoys them!
Reply
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
Ashley Fehr says
Yes they hold up perfectly in the freezer!
Reply
Rachel Conners says
These cookie cups look amazing! I love anything with Oreos…too good, and I would totally devour too many of them. Pinned!
Reply
Ashley says
Thanks Rachel! LOVE Oreos too!
Reply
These look so awesome!! I love that you added MORE CHOCOLATE! LOL, you can never have too much chocolate! Perfect little bite sized treats!
Reply
Ashley says
Lol. That’s what I thought! Thanks Jess 🙂
Reply
Wow! Just, wow. Those look like the perfect cookie. More chocolate was the right call! Let’s be honest, more chocolate is always the right call! Love these! Pinned!
Reply
Ashley says
Haha, glad we’re on the same page Stacey!
Reply
Kelley says
These are like little clouds of heaven! They look amazing.. and the frosting..mmm. I need to make these soon!
Reply
Ashley says
Thanks Kelley!
Reply
Oh my gosh, WOW! How awesome do these look? Seriously this is my kinda cookie-cup heaven right here! Love the whole double-cookie/double choc action going on. Perfection. 😀
Reply
Ashley says
Haha, thanks Sarah! I’m glad you’re on the same page!
Reply
Meg @ The Housewife in Training Files says
Oh the frosting is totatly needed!
Reply
Ashley says
I agree!
Reply
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