Rolo Thumbprint Cookies

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Rolo Thumbprint Cookies

If you love chocolate and caramel (and really, who doesn’t?), these Rolo Thumbprint Cookies are about to become your new favorite treat.

Soft, chewy chocolate cookies with a rich melted chocolate center, topped with a gooey caramel Rolo — every bite melts in your mouth. They’re simple, beautiful, and taste like a bakery specialty made right in your own kitchen.

Whether you’re making them for the holidays, gifting them in cookie boxes, or baking just because you deserve something sweet — these cookies never fail to impress.

Ingredients

• 1 cup butter, softened
• 1 cup granulated sugar
• 1 cup brown sugar, packed
• 2 large eggs
• 2 teaspoons vanilla extract
• 2 cups all-purpose flour
• 1 cup unsweetened cocoa powder
• 1 teaspoon baking soda
• 1/4 teaspoon salt
• 1 cup semi-sweet chocolate chips (for filling)
• 12 Rolo candies, cut in half

Instructions

1. Preheat oven:
   Set your oven to 350°F (175°C) and line two baking sheets with parchment paper.
2. Make the dough:
   In a large mixing bowl, cream together the butter, granulated sugar, and brown sugar until light and fluffy. Add eggs and vanilla, and beat until smooth.
3. Add dry ingredients:
   In a separate bowl, whisk together flour, cocoa powder, baking soda, and salt. Gradually add to the wet ingredients until fully combined.
4. Form the cookies:
   Scoop about 1 tablespoon of dough, roll into a ball, and place on your baking sheet. Use your thumb or the back of a teaspoon to press a small indentation in the center of each cookie.
5. Bake:
   Bake for 9–10 minutes, or until the edges are set but the centers are still soft.
6. Add the chocolate filling:
   While the cookies are still warm, melt the chocolate chips in a microwave-safe bowl in 20-second increments, stirring until smooth. Spoon a small amount of melted chocolate into each thumbprint.
7. Top with Rolos:
   Cut each Rolo candy in half and place one half into the melted chocolate center of each cookie. Let them rest until the chocolate firms up slightly — or chill for a few minutes to speed it up.

Jennie’s Thoughts

There’s something about chocolate and caramel that feels like a hug in cookie form. When I first made these Rolo Thumbprint Cookies, my whole kitchen smelled like a candy shop — warm cocoa and buttery caramel swirling together.

I love how easy these are to make, yet they look so fancy. Every time I serve them, people think I spent hours on them. The truth? They come together so quickly that I usually bake a double batch — one to share and one to keep!

These cookies are perfect for Christmas cookie trays, but honestly, I make them all year long. With their soft centers and that irresistible caramel top, they never last long in my house.

Tips & Variations

• Try sea salt: Sprinkle a pinch of flaky sea salt over the top for a salted caramel twist.
• Make ahead: The dough freezes beautifully. Roll into balls and freeze for up to 3 months — just thaw slightly before baking.
• Swap Rolos: Use mini peanut butter cups or chocolate-covered caramels for a fun variation.

Why You’ll Love These Cookies

• Soft, rich chocolate cookie base
• Gooey caramel and chocolate center
• Perfect for holidays or gifting
• Crowd-pleasing flavor that everyone loves

Jennie’s Favorite Cookie Recipes

• Salted Caramel Chocolate Chip Cookies
• Mini Oreo Cheesecakes

These Rolo Thumbprint Cookies are the kind of treat that makes everyone stop mid-bite and say, “Oh my gosh, what are these?!” They’re rich, elegant, and full of that homemade charm that makes baking so rewarding.

Bake a batch, pour a glass of milk (or coffee!), and enjoy every sweet, chocolatey, caramel-filled bite.