Chocolate Rolled Crispy Cookies With Cherry Chocolate Filling

Making Christmas cookies has been a tradition at my house for over 50 years. I always try to include at least one new cookie on my cookie trays. This year I was inspired by the famous rolled and filled crispy cookies sold in most grocery stores. They are very light and crispy and I always enjoy them very much. I told myself I should really try to make them some time. Since they are so unique, I decided this could be a great idea for the Cookies Instructables. And what about chocolate rolled crispy cookies, filled with cherry-flavored chocolate? They sounded like the perfect experiment! Here is my resulting cookie!

Tools

medium bowl

whisk

tablespoon measure

8-inch non-stick skillet

spatula

cutting board

12 straws

kitchen shears

air fryer with air frying basket

Cookie ingredients

1 cup all-purpose flour

2 tablespoons cocoa powder

1/2 cup confectioners sugar

1/2 teaspoon baking powder

1/4 cup canola oil

1/2 teaspoon vanilla extract

3/4 cup milk

cooking spray

In a medium bowl, whisk flour, cocoa powder, confectioners sugar and baking powder.

Whisk in the oil, vanilla and 1/2 of the milk.

Add and whisk in the remaining milk until mixture stirs smooth.

Place the skillet over medium heat for 2 minutes to preheat.

Spray the skillet with cooking spray.

Spoon 2 tablespoons of the batter onto the hot skillet.

Quickly swirl and spread the batter evenly over the bottom of the pan.

Cook until the edges start to separate from the pan.

Use a spatula to flip the cookie over.

Cook for another 30 seconds.

Remove the cookie from the pan to a cutting board or work surface.

Immediately roll it over a straw being careful not to burn your finger tips. Place the rolled cookie on a large cutting board or work surface.

Spray the pan again with cooking spray. Repeat the steps making more cookies in the skillet and roll each on a straw. The batter will make 12 rolled cookies.

Remove the straws. Use kitchen shears to cut each end straight.

Line up cookies on the air fryer basket, leaving a small space between each cookie. Preheat the air fryer to 390 degrees F. Place the tray of cookies in the air fryer. Air fry the cookies for 10 minutes.

Remove the air fryer basket and carefully flip the cookies over. Air fry for 10 minutes. Continue air frying the cookies at 10 minute intervals until they feel crispy.

Repeat the processes of air frying the remaining cookies until crisp. Allow to cool completely before filling.

Tools

1 quart saucepan

small rubber scraper

sharp knife

cutting board

2 zip-locking sandwich bags

pretty serving plate

Chocolate Cherry Filling Ingredients

1/4 cup maraschino cherries, drained well

1 tablespoon plus 1 teaspoon maraschino cherry juice

1 cup semisweet chocolate chips

1/2 cup sweetened condensed milk

Topping

Christmas sprinkles

In a small saucepan combine chocolate chips and sweetened condensed milk. Heat over low heat, stirring occasionally, until the chocolate is melted and smooth. Remove from heat.

Stir the maraschino cherry juice into the chocolate mixture.

Make a small snip on the bottom corner of each zip-locking plastic bag. Spoon half of the cherry chocolate into each of the bags.

Dice the cherries on the cutting board.

Put a cherry piece into the end of a rolled cookie. Pipe in some chocolate cherry mixture. This pushes the cherry piece toward the center of the cookie. Put cherry pieces and pipe some chocolate into both ends to assure the cookie is filled. The chocolate should be at the ends.

Using the second bag of melted cherry chocolate, pipe a squiggle design onto the top of each cookie. Place a cherry piece onto the center of each.

Sprinkle the cherry chocolate squiggles with the sprinkles! They make the cookies look so festive!

These cookies make me so very happy! They came out very crispy and flavorful! I love the creamy cherry chocolate on the inside and on top. The cherries are tasty and the Christmas sprinkles look so pretty! I hope you enjoyed seeing how I made these unusual cookies. I know my family will enjoy eating them as much as I do!