Chocolate Cookies … with Rolos!

This Quadruple Chocolate Pudding Cookie recipe is my favorite chocolate cookie recipe. I couldn’t resist ‘improving’ upon it by stuffing these cookies with Rolos. Insanely good. They’re thicker, bakery-style cookies that are bold and rich, not overly sweet, and are oozing with gooey caramel and melted chocolate. The cookies are super soft, tender, slightly chewy, and are made for serious chocolate lovers. There’s chips, chunks, cocoa, and chocolate pudding. The cookies are just exploding with so much chocolate in every bite. The way chocolate cookies should be. Getting to center of the cookies with that caramel just waiting to be devoured is obviously the best part. They’re going to be a tough act to follow.

Ingredients in Chocolate Rolo Cookies

To make these chocolate pudding cookies with Rolos in the middle, you’ll need the following ingredients:

Unsalted butter Light brown sugar Granulated sugar Eggs Vanilla extract Instant chocolate pudding mix Unsweetened cocoa powder All-purpose flour Baking soda Salt Dark chocolate bar Semi-sweet chocolate chips Rolo candies

How to Make Rolo-Stuffed Chocolate Cookies

The caramel-stuffed cookies are easy to prepare, but you need to allow time for the dough to chill before baking it. Here are the basic steps for making the cookies:

Tips for Making Chocolate Rolo Cookies

Check the packaging of your pudding mix to ensure it’s instant. You can NOT use cook and serve or sugar-free pudding mix for this recipe. Likewise, check that your cocoa powder is unsweetened. If it’s been sweetened, your cookies will taste sickly sweet. I used chopped dark chocolate and semi-sweet chocolate chips, but you may throw in whatever chocolate you have on hand.

More Chocolate Caramel Cookies:

Chocolate Chip Turtle Cookies — The BEST chocolate chip cookies stuffed with TURTLES candies!! Soft, chewy, and buttery with caramel and chocolate! Tried this recipe? Leave a review! Consider leaving a 5 star rating if you’ve made and loved one of my recipes! Peanut Butter and Chocolate Turtle Cookies — Soft and chewy peanut butter chocolate cookies with a Turtle in the middle and drizzled with salted caramel. So darn good! Better-Than-Girl-Scout Samoas Cookie Bars — Resembles Samoas but BETTER!! These coconut caramel cookie bars feature an Oreo crust topped with coconut, chocolate chips, and drenched in salted caramel!! Homemade Little Debbie Star Crunch — Caramel and butter are melted and combined with marshmallows to create a gooey sweet sauce for crispy rice cereal, which provides texture and crunch. It’s almost better than the real thing! Caramel-Stuffed Chocolate Chip Cookie Cups — The cookies are buttery soft with squishy interiors, and a slight chewiness around the edges. The best part is finding a big buttery, rich caramel in the center!

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