Cinnamon Rolo Thumbprint Cookies: Gooey Chocolate Caramel Treats

A gooey caramel center and a dusting of cinnamon sugar elevate these Rolo Cookies into something special. They strike the perfect balance between soft, chewy texture and warm cinnamon sweetness, with hidden pockets of melted chocolate and caramel in every bite.

A stack of cinnamon sugar cookies stuffed with caramel candies on a towel.

Cake mix cookies are one of the easiest and most satisfying cookie types to make: they capture that homemade flavor while saving time. They come together quickly and are forgiving for bakers of any skill level.

If you like cake mix cookies, try classics like cookies and cream, funfetti cake mix cookies, or chocolate mint cake mix cookies. For this recipe, an extra vanilla cake mix and a bag of caramel candies inspired a decadent twist—Rolo-stuffed cinnamon sugar cookies.

Why Make Cookies with Rolos

Adding a caramel candy to a cinnamon sugar-coated cake mix cookie brings an extra layer of flavor and texture. These Rolo cookies are quick to prepare, bake up soft and puffy, and hide a delightful, molten caramel center.

  • Simple ingredients and minimal prep make them easy to bake.
  • Rolling the dough in cinnamon sugar gives them a snickerdoodle-like flavor.
  • Each cookie holds a surprise Rolo center—warm caramel wrapped in chocolate.
  • The cookies stay soft for several days when stored properly.

Ingredients Needed

A white board with bowls of ingredients needed to make cinnamon cake mix cookies.

This easy Rolo cookie recipe relies on a vanilla cake mix as the base, plus butter, cream cheese, an egg, cinnamon sugar for coating, and Rolos for the hidden centers.

  • Vanilla cake mix – Use only the dry mix powder; do not prepare the cake mix according to box directions.
  • Unsalted butter – Soften to room temperature for easier mixing.
  • Cream cheese – Adds moisture and a tender, puffy texture.
  • Egg – Binds the dough and adds structure.
  • Rolo candies – Unwrap before inserting into the dough to create a gooey caramel core.
  • Cinnamon sugar – Use store-bought or make your own for the snickerdoodle-style coating.

How to make Rolo Cookies

Four pictures collaged together showing how to make cake mix cookies rolled in sugar.

These caramel-stuffed cookies are straightforward to prepare. The dough needs time to chill, but active prep time is short.

  1. Make the dough. In a large bowl, beat the dry cake mix with the softened butter, egg, and cream cheese until a soft dough forms.
  2. Chill. Cover and refrigerate the dough for at least 60 minutes to firm it up and reduce spreading during baking.
  3. Stuff each cookie. Divide the dough into 24 even portions. Flatten each portion, place an unwrapped Rolo in the center, and wrap the dough around the candy to enclose it.
  4. Coat and bake. Roll each ball in cinnamon sugar, place on a baking sheet (about 12 per sheet), and bake at 350°F (175°C) for about 10 minutes. Let the cookies cool on the sheet for a couple of minutes before transferring to a cooling rack.
Three cinnamon sugar cookies on a white plate.

Tips and Tricks

  • Chill the dough. Chilling prevents excess spreading and improves texture.
  • Unwrap the candies ahead of time. Remove wrappers while the dough chills so they’re ready when you portion the dough.
  • Avoid overbaking. Cookies may seem slightly underbaked when removed; they’ll set as they cool and remain tender.
  • Gently flatten after baking. Cookies will be puffy when they come out. After cooling on the sheet for a couple of minutes, lightly tap the tops with a spatula if you prefer a slightly flatter cookie.
  • Cool completely before storing. Cake mix cookies have the best texture once fully cooled.

FAQs

How many cookies does this make?

This recipe yields about 24 large cookies. For smaller cookies, divide into 36 balls and reduce bake time to around 9 minutes.

What is the best way to store cake mix cookies?

Store cooled cookies in a tightly sealed container at room temperature for 4–5 days. To freeze, place cookies in airtight bags or containers with parchment between layers and freeze for 1–2 months. Thaw in the fridge overnight, then bring to room temperature before serving.

Can you make the dough ahead of time?

Yes. The dough can be prepared 1–2 days in advance and kept sealed in the refrigerator until you’re ready to form and bake the cookies.

Four cookies cut in half and stacked showing a gooey caramel center.

More Cake Mix Cookies

  • Cherry Chocolate Chunk Cookies
  • Peanut Butter and Jelly Cookies
  • Fluffernutter Cookies
  • Peppermint Patty Cookies
  • Snickers Stuffed Cookies
  • Candy Cookies
  • Peppermint Oreo Cookies

If you tried this recipe and enjoyed it, please leave a rating and a comment to share how it turned out.

Recipe

A stack of cinnamon sugar cookies stuffed with Rolo candies on a towel.

Rolo Cookies

Yield: 24 cookies
Prep Time: 45 minutes
Cook Time: 10 minutes
Total Time: 55 minutes

A gooey caramel center and cinnamon sugar takes these Rolo Cookies to a whole new level. They are the perfect balance of soft, chewy goodness and cinnamon sweetness. Plus you get a hidden bonus – gooey pockets of chocolate and caramel!

Ingredients

  • 1 white cake mix (dry mix only)
  • 1 large egg
  • 8 tablespoons unsalted butter, softened
  • 4 ounces cream cheese, softened
  • 24 Rolo candies, wrappers removed
  • 3–4 tablespoons cinnamon sugar

Instructions

  1. Beat together the cake mix, egg, softened butter, and cream cheese until a soft dough forms. Refrigerate for at least 60 minutes.
  2. Preheat the oven to 350°F (175°C) and prepare a baking sheet.
  3. Scoop and roll the dough into 24 even balls. Press each ball flat, place a Rolo in the center, and seal the dough around the candy.
  4. Roll each cookie in cinnamon sugar and place on the baking sheet. Bake for 10 minutes. Let cool on the sheet for 2 minutes before transferring to a cooling rack.
  5. If desired, gently tap the tops with the back of a spatula after a short cool-down to slightly flatten. Allow cookies to cool completely before storing.

Notes

  • Chill the dough: Essential for controlling spread and achieving the best texture.
  • Unwrap candies in advance: Have Rolos ready while you portion the dough.
  • Do not overbake: Cookies will finish setting as they cool.
  • Cool completely: For the best texture and to avoid soggy centers, let cookies cool before storing.
Nutrition Information (per serving):

Yield: 24 • Serving Size: 1

Calories: 93 • Total Fat: 7g • Saturated Fat: 4g • Unsaturated Fat: 2g • Trans Fat: 0g • Cholesterol: 23mg • Sodium: 40mg • Carbohydrates: 6g • Fiber: 0g • Sugar: 5g • Protein: 1g

Nutrition facts are estimates and not guaranteed. For specific dietary advice, consult a registered dietitian.

© Jocelyn @ Inside BruCrew Life
Cuisine: American
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Category: Cookies

*This post was originally published October 2014 and updated September 2021.