Chocolate Rolo (Caramel) Cookies

One of my most profound discoveries from my college years was coming across this Chocolate Rolo (Caramel) Cookies recipe among the little recipe books stuffed in shelves at the supermarket checkout line.  Over the years, I’ve made these cookies for nearly every occasion, celebration, commiseration,etc., and anyone who  knows me remotely well and/or has lived in somewhat close proximity to me has at some point in their lives tried these cookies.  The soft, fudgey chocolate cookie with slightly crisp edges gently cradles a single Rolo in the center, which right out of the oven oozes with caramel when you split the cookie down the middle.  After the cookies have cooled a bit, the caramel firms up to a chewy texture which provides yet another dimension to the cookie.  I’ve made a few tweaks to the recipe over the years so you could say it’s reached the “old family recipe” status of awe.

A few minutes out of the oven…
Chocolate Rolo Cookies- 1

Chocolate Rolo (Caramel) Cookies

(The original recipe is from Pillsbury, but I’ve made a few tweaks to it over the years.)
Make approximately 4 dozen (or more) cookies

Ingredients

2 1/2 cups all-purpose flour
3/4 cup unsweetened cocoa powder [I like to use half unsweetened cocoa powder (Penzey’s makes a good one) and half sweetened cocoa powder (I like Ghiradelli sweet ground chocolate).  I feel like this combo adds more depth to the chocolate flavor.]
1 teaspoon baking soda
1/2 teaspoon salt
1 cup granulated sugar
1 cup firmly packed dark or light brown sugar
1 cup (2 sticks) butter, softened
1 tablespoon vanilla
2 large eggs
48 Rolo® Chewy Caramels in Milk Chocolate, unwrapped (from 13-oz. pkg.)
Sugar for rolling cookies

Directions

1. In medium bowl, stir together the flour, cocoa powder, baking soda, and salt; set aside.
2. In large bowl, beat together 1 cup of sugar, brown sugar, and butter until light and fluffy. I recommend using a stand mixer if you have one to ensure everything is mixed really well. Scrape down the bowl as needed.
3. Add the vanilla and eggs, and beat well. Scrape down the sides of the bowl as needed.
4. Gradually add the flour mixture to the wet ingredients, and make sure everything is mixed well (scrape down the bowl), but do not overmix the dough.
5. Cover the dough with plastic wrap, and refrigerate it for 30 minutes or more until the dough firms up a bit.
6. Preheat the oven to 375°F. For each cookie, scoop about 1 tablespoon of dough, and wrap it around one Rolo, making sure to completely cover the Rolo. (Note: If the dough doesn’t fully cover the Rolo, the caramel will melt and leak out of your cookie while baking.)
7. Roll the dough into a ball. Then roll the dough ball in sugar to create a light coating.
8. Place cookies approximately 2 inches apart on ungreased cookie sheets or cookie sheets lined with parchment paper.
9. Bake at 375°F for 7 to 10 minutes or until the cookies are set and the tops are slightly cracked. They will still be a bit soft and puffy, but do not overbake as the bottoms may burn.
10. Let the cookies cool on the cookie sheet for about 2 minutes. This is important because the cookies are really delicate right out of the oven and can break easily. Plus, their centers are heavy (because of the caramel), and if you move them before they’ve firmed up a little, the centers will fall out. Then remove the cookies from the cookie sheets and cool on a wire rack for 15 minutes or until completely cooled.

Notes: I highly recommend eating some cookies before they’re completely cooled so that you can experience the caramel oozing out of them. However, be very careful as the caramel can be hot.

These cookies are best the day that they’re baked, and they will keep well for about 1-2 days. After that they get a bit dry and crumbly.

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