Rolo Stuffed Cookies

Rolo Stuffed Cookies are soft-baked chocolate chip cookies stuffed with Rolo candy pieces. You won’t be able to stop at one, so just say “YOLO” and have two. 

You know what rolo rhymes with? YOLO. (For any of you out there who do not know what this term is, it means “You Only Live Once.” It is said a lot in pop culture, supposed to be used when one is taking risks or doing fun stuff, or as a life motto, but only about 2% of the population actually take it seriously, the other 98% use it as a joke. I belong to the 98%.)

But you might feel the need to (jokingly) use this phrase when eating these Rolo Stuffed Cookies. When you want to have more than one (which you probably, most definitely will) just think to yourself “YOLO” and have another.

So yes, Rolo Stuffed Cookies are very good. The cookie itself is better than your average cookie- a little richer and more unique of a flavor- and then filled with ooey-gooey-chocolate-coated caramel goodness, well, they’re fantastic. And then there’s salt on top. When has salt ever hurt anything? Never. Unless you have too much and your tongue shrinks. Don’t put that much on these. It might ruin the experience a little.

Another plus: Rolo Stuffed Cookies are very simple! And if you were ever just craving cookies, the ingredients are all simple enough to probably have on hand.

If you do not have Rolos on hand, these can easily be stuffed with just about anything. Suggestions? Girl Scout cookies, Oreos, Reese’s, mini candy bars of your choosing. Just about anything. Even vegetables. But that might be disgusting. So don’t use those. 

You can also always stuff any type of chocolate chip cookie. One of my favorite recipes is the New York Times Best chocolate chip cookies stuffed with Girl Scout Cookies (Samoas are my favorite).

I would like you to admire and appreciate how well these Rolo Stuffed Cookies are stacked, because- despite my professional cookie stacking skills- shortly after these pictures, this happened:

So eventually I just settled for a sort of pile thing instead of a stack:

-Audrey

Rolo Stuffed Cookies

• Author: Molly
• Prep Time: 10 minutes
• Cook Time: 13 minutes
• Total Time: 1 hour
• Yield: 1 dozen cookies 1x

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Ingredients

• 2 and 1/4 cup all-purpose flour
• 1 teaspoon baking soda
• 1 and 1/2 teaspoons cornstarch
• 1/2 teaspoon salt
• 3/4 cup (or 1 1/2 sticks) unsalted butter, melted
• 3/4 cup light brown sugar, loosely packed
• 1/2 cup granulated sugar
• 1 large egg + 1 egg yolk
• 2 teaspoons vanilla extract
• 1 cup chocolate chips, divided
• 15 Rolo candies
• sea salt

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Instructions

1. Toss together the flour, baking soda, cornstarch and salt in a large bowl. Set aside.
2. In a medium size bowl, whisk the melted butter, brown sugar, and white sugar together until no brown sugar lumps remain. Whisk in the egg, then the egg yolk. Finally, whisk in the vanilla. Pour the wet ingredients into the dry ingredients and mix together with a large spoon or rubber spatula. The dough will be very soft. Fold in 1/2 cup chocolate chips. They may not stick to the dough because of the melted butter, but do your best to have them evenly dispersed among the dough. Cover the dough and chill for 2 hours, or up to 3 days. Chilling is mandatory, the longer the better.
3. Take the dough out of the refrigerator and allow to slightly soften at room temperature for 10 minutes.
4. Preheat the oven to 325F degrees. Line two large baking sheets with parchment paper or silicone baking mats. Set aside. Unwrap the Rolos and have your 1/2 cup of chocolate chips in a pile ready to be used.
5. Roll the dough into balls, 1.5 Tablespoons each. You’ll have about 30 balls, give or take. The dough will be crumbly, but the warmth of your hands will allow the balls to stay intact. Make a thumbprint into one dough ball and press the Rolo inside. Cover the Rolo with another dough ball and mold the two dough balls around the Rolo, making sure it is completely wrapped inside. See photo above for a visual. Gently press down on the large cookie dough ball to slightly flatten and press a few more chocolate chips on top. Sprinkle with sea salt. Put 7-8 balls of dough onto each cookie sheet. Put one cookie sheet into the refrigerator as you bake batch #1. Bake the cookies for 12-13 minutes. The cookies will look very soft and underbaked. Do not bake longer than 13 minutes. They will continue to bake on the cookie sheet. Allow to cool on the cookie sheet for 10 minutes before moving to a wire rack to cool completely. If the cookies still look too puffy when you remove them from the oven, gently press down on them a little more.