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.
Oreo-Stuffed Double Chocolate Cookie Cups
written by Ashley Fehr
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
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Isadora @ she likes food says
Hahaha! I think I need a pair of maternity pants and not because I’m expecting a baby! For some reason I don’t really like oreos by themselves but cookies and cream is one of my favorite ice creams and I want to eat all of these cookie cups!
Ashley says
Oh man, cookies and cream is my favorite!
Cyndi - My Kitchen Craze says
Your co-workers are lucky to have you!! And these cupcakes look amazingly delicious! That oreo in the middle is perfect. And maternity pants are the “new” in thing so no worries!! 😉
Ashley says
Haha, I’m glad Cyndi! I don’t know when I’ll be getting out of them… 🙂
Kelly - Life Made Sweeter says
These look heavenly! Oreos are my weakness and stuffed inside double chocolate cookie cups? Sounds amazing and that frosting has me totally swooning!
Ashley says
Thanks Kelly!
Medha @ Whisk & Shout says
These look perfect! Love all the oreo you got in these cupcakes! The shot of the insides of the cakes is awesome 🙂
Michelle { A Latte Food } says
I don’t have maternity pants, but I’d gladly wear a pair so that I could stuff myself silly with these cups of what I think is pure joy. Oh my goodness, I am in love with these.
Ashley says
Haha, it’s TOTALLY worth it Michelle!
Allie | Baking a Moment says
Oh my gosh, these are totally over the top and I love it! So much chocolatey goodness… drool!
Ashley says
Thanks Allie!
Beth says
WOOHOO!!! I think the sugar is already running through my veins! I love these, because I love over the top recipes!
Ashley says
Haha, thanks Beth!
Natalie @ Tastes Lovely says
Your coworkers must love you! Cookies inside a cupcake? Amazing! Plus, they got to see your cute little baby, which is even sweeter.
Ashley says
Thanks Natalie! I don’t think they minded 🙂
Shashi at RunninSrilankan says
Let me just say this Ashley – it’s just so unfair to have to ogle that cross section of a cupcake with an oreo peeking through, from this side of the screen! You can never go wrong with more chocolate- eva!
Ashley says
Haha, SO sorry about that Shashi! Thanks for your support 😉
Tina @ Tina's Chic Corner says
First, you had me at the title (before even seeing the gorgeous pics). Second, I’m cracking up over your first line.
I’m guessing that I won’t be able to stop at just having one of these! Yummers.
Ashley says
Haha, thanks Tina! Stretchy pants are a blessing and a curse!
Kristine @ Kristine's Kitchen says
I am living in my maternity leggings and loving it. I was just telling my husband yesterday, that I need to buy a pair of non-maternity leggings because they are just too comfortable and I want to be able to wear them even once the maternity pants are no longer acceptable to wear. 🙂 I’m also enjoying the excuse to eat whatever I want right now – and these Oreo cookie cups look like the perfect way to satisfy my chocolate cravings! Pinned!
Ashley says
Lol, I JUST started working out today. I LOVE leggings, and I actually bought a bunch more leggings and yoga pants knowing that I was going to be on maternity leave. That being said, occasionally I need to leave the house so I try not to eat all the chocolate I want… 🙂
Shinee says
Oh so pretty! That frosting is a must, looks so perfect and complete! I wish I was your co-worker. Haha
Ashley says
Haha, thanks Shashi!
marcie says
There’s only one packaged cookie that I love, and that’s Oreos — there’s just nothing like them. I love cookies & cream themed desserts, and these cookie cups look amazing, Ashley! And I do my best over the top stuff when I know I’m taking the bulk of it elsewhere because yeah…the pants won’t fit if I keep them. haha Your co-workers must have loved these!
Ashley says
It works perfectly! That way there’s no temptation, otherwise I would definitely eat them all! Lol. Luckily now that I’m at home the hubs is working in town and I can just send the leftovers with him back to HIS coworkers. Lol
Nora @ Savory Nothings says
My baby girl is five months now and I’m still in maternity pants. Not because my normal pants don’t fit but this stretchy band is just so amazingly comfortable and I can move in every direction without anything pinching me! Slightly embarrassing but oh well 🙂
I should definitely not be all over these wonders of oreo and chocolate you produced here – or else maternity pants will definitely be my only option in the pants department!
Ashley says
I think it’ll be a little while longer before the pants fit, but I DID start working out today, so it’s a step. Lol. And then I made 2 batches of cookies, because, you know, this food blog thing. 🙂
Joanie @ ZagLeft says
These look amazing! All that chocolate sounds heavenly. I’m sure your co-workres were thrilled!
Ashley says
And I thought they were just happy to see me…? Lol.
Tonia from TheGunnySack says
I need to make some of these for myself…I mean…for my husband to bring to work. They look amazing!
Ashley says
Haha, obviously…. I totally knew what you meant! Thanks 🙂
Ginny McMeansk says
I think I need to buy some maternity pants. Maybe my yoga pants will work. Those look so wonderful.
Ashley says
Haha, I definitely have my share of yoga pants! Thanks 🙂
Alice @ Hip Foodie Mom says
Ashley, hey, over the top is always good when bringing sweet treats to co-workers!!! oh my gawd, these are fabulous!!! I want some oreo-stuffed-double-chocolate-cookie-cups goodness today!!! love!
Ashley says
Right?! I can honestly say I didn’t even eat the whole batch myself! Thanks Alice 🙂
Jocelyn (Grandbaby cakes) says
I’m too in love with these. I think I would eat that entire plate. The oreo inside is fantastic!
Ashley says
Thanks Jocelyn!
Gayle @ Pumpkin 'N Spice says
I’m sure your co-workers will devour these cups, Ashley! Anything filled with oreos is bound to be a winner. I love these, looks amazing!
Ashley says
Thanks Gayle!