Wednesday, May 5, 2021
HomeRecipe ReviewsDessertsOreo-Stuffed Double Chocolate Cookie Cups

Oreo-Stuffed Double Chocolate Cookie Cups

I feel like I need to make something rich and decadent. Maybe it’s a reaction to the healthy One-Pot Vegan Mushroom Stroganoff I just made. Ever feel like you deserve a treat after you’ve “been good”? I do, and way too often! Well, today’s recipe promises to be that rich, decadent treat I’m craving. These Oreo-Stuffed Double Chocolate Cookie Cups are loaded with chocolate and combines cookies and brownies into a cupcake-like creation. As far as I’m concerned, that’s pure genius! Join me in discovering this recipe and find out if it’s as good as it sounds.

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!

Recipe Author: Ashley Fehr at The Recipe Rebel
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The Ingredients

These Oreo-Stuffed Double Chocolate Cookie Cups are loaded with chocolate! White chocolate, milk chocolate, cocoa powder, and chocolate cookies. I’ve died and gone to heaven!

I was able to find everything at my usual grocery store, even white chocolate chips. The recipe just says chopped white chocolate, so I figured using chips would be just about the same thing.

I did have to substitute Whole Foods' 365 sandwich cookies for the Oreos, though, and they aren’t quite as good as the real thing. I think Oreos have more chocolate in them, but these weren’t terrible.

Oreo-Stuffed Double Chocolate Cookie Cups Ingredients
Sandwich cookies, milk, granulated sugar, powdered sugar, vanilla extract, mini chocolate chips, cocoa powder, mini white chocolate chips, baking soda, butter, eggs, and flour

The Process

The first thing to note with this recipe is that it makes 24 Oreo-Stuffed Double Chocolate Cookie Cups, so you will need an extra muffin tin. I ordered an extra one, and I’m so glad I did. By making all 24 cookie cups at once, I was able to distribute the brownie batter without coming up short.

The next tip is to set the sticks of butter on your counter to soften for a couple of hours before you plan to start baking. It’s not something that’s specified in the recipe, but it will make beating the batter and frosting much easier. It will also make the frosting smoother. Don’t believe me? This cake shows what happens when your butter is too cold, and it’s not pretty.

Here’s how my time was spent:

  • 23 minutes to prep the cookie cups
  • 21 minutes to make the frosting*
  • 9 minutes to frost and garnish the cookie cups
  • 53 minutes total

*Includes baking the cookie cups for 14 minutes.

Making the Cookie Cups

Okay, so now that we have all our muffin tins, it’s time to get down to baking! This recipe is nicely divided into sections, so it’s easy to follow. It starts with making the brownie batter, and you’ll need a mixer for this part since the batter gets thick. I think you could use a hand mixer if you had to, but a stand mixer is the way to go here.

Once you have that thick, chocolatey batter mixed up, start filling your muffin tins. I used a regular teaspoon to scoop out dollops of batter. Then I used the back of the spoon and my fingertips to smooth it into the bottom of the muffin tins. This part was a little messy but not difficult.

Filling the muffin tins with brownie batter and sandwich cookies
Filling the muffin tins with brownie batter and sandwich cookies

After adding the cookies, it was the same to add the tops of the cookie cups. I came up a little short here, but it was easy to remove a little bit of batter from some of the first cups I finished to make up for the shortage.

It all worked out in the end, but I have to warn you to work quickly. As the batter warms up, it gets stickier and stickier. I had to spray my fingertips with cooking spray toward the end to keep the batter off them and in the muffin tin.

Making the Frosting

While the brownies were baking, I rinsed off the beaters and mixing bowl so I could make the frosting. The recipe says frosting is optional, but c’mon! It’s not Oreo without the cream filling, er, topping.

This is where I should have paid more attention, and things would have gone faster. The white chocolate and milk need to be melted together in the microwave then set aside to cool for 15-20 minutes.

If I had planned right, I would’ve started with this step before I made the cookie cups. Then the chocolate mixture would have been ready to go when I wanted to start the frosting. Since I didn’t plan ahead, I had to wait for the mixture to cool. Kinda boring, but I did have some dishes to do to pass the time. Funsies!

After that, making the frosting was very simple. The powdered sugar did its usual thing and dusted my stand mixer and everything within a 1-foot radius. Covering the mixer with a tea towel would have helped contain the dust, but I forgot it.

Mixing up the white chocolate frosting in a stand mixer
Mixing up the white chocolate frosting in a stand mixer

Frosting and Decorating

With the cookie cups cooled and the frosting ready, it was time to decorate. It took me about 10 minutes to remove the brownies from the muffin tins, add a dollop of frosting and cut up extra cookies for a garnish.

I came up a little short with the frosting, so don’t go too crazy with it. You can always add a little more if you have extra. I scooped off a little from the ones with a lot of frosting to make up for the ones that didn’t have enough at the end. everything worked out, and I topped them all with cookie bits.

However, I don’t recommend frosting all of your brownie cookie cups at once. The reason is the brownie gets hard when you store it, and you need to reheat it in the microwave for a few seconds. If it has frosting on it, the frosting melts and it’s not as good somehow.

Next time, I will keep the frosting in a separate sealed container and add it as I eat the cookie cups. That will allow me to reheat them as needed (and they are soooo much better warm!). I supposed I could also keep a container of cookie bits, but I’ll probably skip that part since the garnish doesn’t really affect the taste.

A cookie cup with frosting and garnish
A cookie cup with frosting and garnish

So how was it?

Clear & Accurate Directions
Accurate Time(s)
These Oreo-Stuffed Double Chocolate Cookie Cups are a chocolate lover's dream come true! Three types of chocolate are combined with sandwich cookies and brownies into a cupcake-like creation that's topped with Oreo filling-like frosting. Magical! The outside of the brownies is a little crispy, and the inside is nice and chewy. And then there's that frosting! It really is a creamier version of Oreo cookie filling. The recipe breaks down the steps to make this decadent dessert creation, and I found it very easy to follow. I did find a couple of things I would have done differently to make things smoother, but nothing too major. All in all, this is a solid recipe that I will be making again.
I'm Candice, and I'm The Hungry Pinner. I created this blog to share my love for cooking and my experiences with the MANY recipes I've found on Pinterest over the years. Join me as I blog my way through those recipes to find out if they are worth trying yourself.


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