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Double Chocolate Caramel Cookie Cups

Prep Time 30 mins
Total Time 39 mins
Servings 48

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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.

Chipits

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.

Double Chocolate Caramel Cookie Cups: super easy cake mix cookie cups stuffed with caramel, topped with a chocolate truffle and Skor bits! www.thereciperebel.com

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.

Anyway.

Double Chocolate Caramel Cookie Cups: super easy cake mix cookie cups stuffed with caramel, topped with a chocolate truffle and Skor bits! www.thereciperebel.com

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.

Double Chocolate Caramel Cookie Cups: super easy cake mix cookie cups stuffed with caramel, topped with a chocolate truffle and Skor bits! www.thereciperebel.com

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!

Double Chocolate Caramel Cookie Cups

5 from 1 vote
Double Chocolate Caramel Cookie Cups: super easy cake mix cookie cups stuffed with caramel, topped with a chocolate truffle and Skor bits! www.thereciperebel.com
Prep Time 30 mins
Cook Time 9 mins
Total Time 39 mins
Cuisine American
Course Dessert
Servings 48
Calories 182kcal

Ingredients

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

Instructions

  • 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: 182kcal | 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

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Double Chocolate Caramel Cookie Cups
Prep time:
Cook time:
Total time:
Serves: 48
Double Chocolate Caramel Cookie Cups: super easy cake mix cookie cups stuffed with caramel, topped with a chocolate truffle and Skor bits! www.thereciperebel.com
Ingredients
  • Cookie cups
  • 2 468g 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
  • 1 can sweetened condensed milk
  • 1 3/4 cup CHIPITS Semisweet chocolate chips (or use milk chocolate if you prefer)
  • Hershey Skor bits
Instructions
  1. Preheat oven to 350 degrees and grease 48 mini muffin cups very well.
  2. 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.
  3. Spoon rounded teaspoons into greased mini muffin tins and bake for about 9-10 minutes, until set on top.
  4. 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).
  5. 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.
  6. Let chocolate set completely before serving. Can be stored at room temperature for a few days, or frozen for up to a few months.

Find more recipes from Hershey here!

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. 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!

  4. Stacey @ Bake.Eat.Repeat. says

    Those cookie cups look absolutely incredible Ashley! Congrats on getting picked for the Hershey promo! I saw that 3 days after it was closed and was totally bummed about not being able to throw my name in the hat! Like you say, using all that stuff anyways! I love what you came up with, these look so so good!

  5. Sarah @ The Gold Lining Girl says

    WOW! You’re are one lucky lady! Look at all those baking chips and candies! That’s so exciting! These caramel cookie cups look fabulous! I don’t make cookie cups very often and I have no idea why. They’re awesome and you can stuff the middles with so many delicious things. I need to try these or the Fudge Puddles – those looked amazing too! Thanks for sharing!

  6. Sophie Boss says

    Just new to your blog but love getting your updates and seeing your creations!!!
    Congrats on the sponsor – what a great way to wrap up the year!
    Congrats on all your sucess!

  7. Kelly - Life Made Sweeter says

    You are a rockstar for pumping out all these amazing desserts and dishes with your due date so near. Love Hershey’s and that you used them with the Skor toffee bits in these cookie cups!!! The chocolate truffle and caramel filling sound absolutely heavenly!

    • Ashley says

      Thanks Alice! Bite-sized things ARE awesome, but I tend to eat WAY more of them! Lol. And yes! I am due like… right now. 🙂 Two more days! Of course, that doesn’t mean anything, but I’m secretly hoping it does. We don’t know if it’s a boy or a girl 🙂

  8. Cyndi - My Kitchen Craze says

    These double chocolate carmel cookie cups look out of this world!! Yum! I hate when I have a cooking fail to. Totally bums me out. And to be 9 months preggo on top of it. Poor thing. But all worked out in the end!! Ps I am bummed I can’t enter either. No fair, hehe.. 🙂

  9. Beth @ bethcakes says

    These cookie cups look fantastic! I love that caramel on the bottom! Using a caramel-filled candy is such a great idea. Also what a fun giveaway! Who wouldn’t mind getting a box of chocolate in the mail? 🙂

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