Double Chocolate Caramel Cookie Cups

Prep Time 30 minutes
Total Time 39 minutes
Servings 48

Jump to Recipe

So when I started blogging I thought that it would be much longer before I’d be able to convince anyone to deliver a giant box of chocolate to my door.

I know that these kinds of things happened to really big, successful bloggers but I still feel like such a newbie, totally unworthy of such an incredible opportunity.

chocolate caramel cookie cups stacked with bite taken out of top cookie cup

So, yes, if you haven’t guessed it, the wonderful people at Hershey are sponsoring this post, just in time for your holiday baking. Let me also just say that my freezer was already well-stocked with all flavors of Chipits and Skor bits (Heath I think for my friends further South?). Taking these products and creating something with them is something I would be doing anyway, so I’m super excited that they kindly sent me some extras to keep me going until Christmas and beyond.

*Also, stay tuned because there’s an opportunity for you to have a giant box of chocolate delivered right to your door.


chocolate caramel cookie cups on gold plate with toffee bits on top

I was trying to dream up some totally decadent treat to make with my supplies, and I’ve kind of had cookie cups on the brain since I made these Fudge Puddles.

Obviously, I wanted to make something a little bit different, and I wanted to try to incorporate a couple of different kinds of baking chips into the same recipe.

I had been wondering about taking the Fudge Puddle recipe and making a chocolate cookie up, and adding in some other flavors like caramel and Skor, so I gave it a try.

It was a total fail.

Not that double chocolate, caramel and Skor is ever a fail. But the cookie was just too crumbly and didn’t hold together well.

Now, you can only handle so much failure when you’re 9 months pregnant. So I tried making the cookie cups with this recipe for 4-Ingredient Double Chocolate Cookies. And it totally worked.

two cookie cups stacked with bite taken from the top cookie cup and oozing caramel

I tried adding the caramel centers in two ways: using a chocolate covered caramel candy (a Kiss or Rolo or similar), and adding a teaspoon or so of caramel sauce in the bottom of the cookie cup.

Both tasted amazing (obviously), but the caramel sauce is pretty messy. So I definitely went for the candies.

Considering how many incredible flavors are combined in the cookie cup, there are relatively few ingredients. And pretty much no excuse not to make them!

ashley avatar

Pin this recipe to save for later

Pin this recipe to your favorite board

Double Chocolate Caramel Cookie Cups

5 from 2 votes
Double Chocolate Caramel Cookie Cups: super easy cake mix cookie cups stuffed with caramel, topped with a chocolate truffle and Skor bits!
Prep Time 30 minutes
Cook Time 9 minutes
Total Time 39 minutes
Cuisine American
Course Dessert
Servings 48
Calories 182cal


Cookie cups

  • 2 chocolate cake mixes about 16.5 ounces each
  • 4 large eggs
  • 1/3 cup oil
  • 48 chocolate-covered caramel candies a Kiss or Rolo or similar

Truffle filling

  • 14 oz can sweetened condensed milk
  • 1 3/4 cup CHIPITS Semisweet chocolate chips or use milk chocolate if you prefer
  • Hershey Skor bits


  • Preheat oven to 350 degrees and grease 48 mini muffin cups very well.
  • In a stand mixer, combine cake mixes, eggs and oil and beat until combined. The dough should come together easily. If you need, add an extra tablespoon oil to help it come together.
  • Spoon rounded teaspoons into greased mini muffin tins and bake for about 9-10 minutes, until set on top.
  • Remove from oven and make an indent in the middle of the cookie cup. I used the back of a 1tbsp cookie scoop, sprayed with non-stick spray. Place a candy inside each cookie cup, pressing down gently. Set aside to cool completely before removing from the pan(after cooling in the pan for about 10-15 minutes, I like to gently turn or spin the cookie cups, so that they release from the edges of the pan, and then cool completely. If you try this and they don’t release they are likely too warm and will crumble).
  • Once cookie cups are removed from the pan, heat sweetened condensed milk over medium-low heat and add chocolate chips. Continue cooking and stirring until completely melted. Spoon melted chocolate over candies in cookie cups or use a pastry or ziploc bag with the corner snipped. Work quickly because the truffles set relatively quickly. Sprinkle with Skor bits and press down gently so they set in the chocolate.
  • Let chocolate set completely before serving. Can be stored at room temperature for a few days, or frozen for up to a few months.

Nutrition Information

Calories: 182cal | Carbohydrates: 26g | Protein: 2g | Fat: 7g | Saturated Fat: 2g | Cholesterol: 16mg | Sodium: 177mg | Potassium: 75mg | Sugar: 19g | Vitamin A: 60IU | Vitamin C: 0.1mg | Calcium: 66mg | Iron: 1mg

Want to save this recipe?

Create an account easily save your favorite content, so you never forget a recipe again.

Register Now

Tried this recipe?

Tag @thereciperebel or hashtag #thereciperebel —â€ĻI love to see what you’re making!

Tag @thereciperebel

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

You May Also Like

Reader Interactions


  1. Dorothy Dunton says

    Hi Ashley! I just had to come back and tell you a story. I gave birth to my son on December 13th. I had a three year old at the time and I was trying to get all the Christmas stuff done – I did not want to be in the hospital on Christmas! I finally convinced my doctor that this baby was ready (I was doing a repeat Caesarean) . I was almost ten months pregnant -the doctor kept telling me he wanted to be sure the baby was fully developed. I never did go into labor – my son came into this world at 9.1 pounds with a full head of hair! He’s 32 now and is still my “baby”! 🙂

    • Ashley says

      Wow! I can’t imagine being 10 months pregnant! My littlest girl was born December 16 — right on her due date 🙂

  2. Dorothy Dunton says

    Hi Ashley! The picture of that box looks like of my pantry shelves! When I make mini brownie muffins or peanut butter cookies I push a mini Reese’s peanut butter cup in the center of each one – I’m a sucker for chocolate and peanut butter. Oh, and caramel and toffee and nuts… 🙂

  3. Isadora @ she likes food says

    Haha, you totally deserve a huge box of chocolate delivered right to your door! That sounds like a dream come true! These cookie cups look amazing! I’m kind of a caramel addict and these just look like the best things ever!

Leave A Reply

Have you tried this recipe? Leave a rating