Rolo Cookies

5 from 1 vote

These Rolo Cookies are soft and chewy chocolate cookies filled with a gooey sweet caramel surprise and topped with Rolo pieces! They are so simple to make, no mixer is needed for the cookie dough and with only 30 minutes of chill time, these stuffed cookies will be ready in an hour! Best yet, this Rolo cookie recipe is gluten free, nut free, eggless and can easily be made vegan! If you're a chocolate and caramel lover, these chocolate caramel cookies are for you!

Prep Time15

Cook Time15

Freeze Time30

Total Time1

Course: Dessert

Cuisine: American

Diet: Gluten Free, Vegan

Servings: large cookies

Calories: 266kcal

Author: Lee

Ingredients

1 ¼ cups multipurpose gluten free flour (I use a gluten free multipurpose flour with xanthan gum already in it)
½ cup cocoa powder (I use ¼ cup Natural Unsweetened and ¼ cup Dark)
1 teaspoon baking soda
½ teaspoon kosher salt
2 rounded tablespoons cornstarch mixed with 3 tablespoons water
½ cup unsalted butter or vegan baking stick, melted and cooled
1 ¼ cups light brown sugar , packed
¼ cup plus 2 tablespoons milk
1 teaspoon pure vanilla extract
24 Rolo candies

US Customary - Metric

Instructions

Take 12 of the Rolos and slice each one into equal 4 pieces. You should have 48 pieces. Set aside.
Place the ½ cup unsalted butter or vegan baking stick in a heat safe bowl. Place a paper towel on top of the bowl so the butter doesn't splatter. Microwave in 11 second increments until just melted. Do not let it bubble or brown. Set aside to cool.
Do not microwave it too much. I prefer to microwave it until there is just a little bit of butter left unmelted and then I whisk it and the residual heat melts the rest of the butter.
In a medium bowl, whisk together the 1 ¼ cups multipurpose gluten free flour, ½ cup cocoa powder, 1 teaspoon baking soda and ½ teaspoon kosher salt. Set aside.
In a small bowl, using a spoon, mix together the 2 rounded tablespoons of cornstarch and the 3 tablespoons of water until thin and watery. It will be thick and tacky at first.
Into the cooled melted butter, combine the 1 ¼ cups light brown sugar, the cornstarch water and the 1 teaspoon pure vanilla extract. Whisk until it is all fully combined and blended. It may appear chunky. That's normal.
Starting and ending with the flour mixture, whisk half the flour into the melted butter mixture. Then add the ¼ cup plus 2 tablespoons milk and whisk to combine.
Add in the second half of the flour gently with a spatula. Do not over mix or the dough will become shiny and too sticky.
The dough will be very sticky. Add it to a freezer safe bowl, cover the top with plastic wrap and pop the entire bowl of dough in the freezer for 30 min.
When the dough is almost done chilling, preheat your oven to 325 degrees Fahrenheit and line a baking sheet with parchment paper. Do not grease.
After 30 min, using a large cookie scoop, make 12 scoops with the dough. (I use a 2 ounce cookie scoop).
If the dough is sticking to the cookie scoop, wash the scoop half way through to get off any stuck on dough.
Take one of the dough balls and press your thumb into the center to make a well.
Shove one of the full size Rolos (you should have 12 full size Rolos) into the hole and then cover it up with the dough that’s been pressed to the side.
Place the dough balls about 3-4 inches apart on the parchment lined baking sheet. Bake the cookies at 325 degrees Fahrenheit for 15 minutes.
I only bake 6-8 at a time. Pop the rest of the dough discs in the fridge while the first batch is baking.
Immediately reshape the cookies when they come out of the oven. Use a spatula to push them into a circle.
Then immediately press 3-4 Rolo chunks into the tops of the hot cookies. Just gently press so they stick.
Let the cookies cool on the baking sheet for 5 min before transferring to a cooling rack.

Video

Notes

For smaller cookies: Use a small cookie scoop and bake at same temperature for 12 min. Make sure to keep dough in the fridge in-between baking the batches. Should make 24 cookies.

Vegan: Use a dairy-free gluten free flour, vegan sugar, vegan baking sticks, non-dairy milk and vegan chocolate covered caramels. (See the section above entitled "substitutions and variations" for more info).

All Purpose Flour: I cannot test this due to celiac disease, but use 1 ¼ packed cups of flour (210 grams), ½ packed cup cocoa powder (58 grams) and 3 tablespoons of milk.

Storing: Keep extra cookies in an airtight container at room temperature for up to 3 days in a single layer. Do not stack. If you want the cookies warm and gooey, heat the cookie in the microwave for a few seconds prior to serving. Be careful not to burn your mouth.

Freezing: Wrap dough in plastic wrap and then pop it in a zip top bag. Freeze for up to 30 days. Thaw overnight in fridge prior to use.

Nutrition: The info below is a generated estimate and is not guaranteed to be accurate.

Nutrition