Homemade Tagalong Cookies

These homemade version of the Girl Scout’s Tagalong cookies are so good, it took an incredible amount of will power to not eat a dozen of them as soon as the chocolate set. These are a lot of work, a big mess, and take all afternoon… but they are worth it.

Servings: 36 cookies

1 cup (2 sticks) butter
4 Tbsp. milk, divided

1/2 cup granulated sugar
2 cups all-purpose flour
1/4 tsp. baking powder
3/4 tsp. salt, divided
1 tsp. vanilla extract, divided
3/4 Confectioners’ sugar
8 oz. semi-sweet chocolate
8 oz. dark chocolate
2 Tbsp. shortening

Make cookie dough
Prehet oven to 350 degrees-F. Cream butter and granulated sugar in the work bowl of a standing mixer. In a separate small bowl, combine 2 cups flour, baking powder, and salt. Add flour mixture to the creamed butter. Add 2 Tbsp. of milk and 1/2 tsp. vanilla extract. Chill dough for 30 minutes. Cover two baking sheets with parchment paper. Scoop dough in 1 Tbsp. sections, divide in half and roll into two balls, place balls on the cookie sheet. Place remaining 1/3 cup flour in a small shallow dish. Using a 1/4 measuring cup, press the cup into the flour, then flatten one of the dough balls until dough is visible from the sides of the cup. Place measuring cup back in the flour and press the other dough ball. Repeat until all dough is used.

Bake cookies
Bake dough for 11 to 13 minutes or until slightly browned on the edges. As soon as cookies are removed from the oven, use the back of a spoon or tsp. measuring cup to press an indention in the center of each cookie. Let cookies cool on the cookie sheets for two minutes then transfer to cooling racks to cool completely.

Top with peanut butter
Combine peanut butter, Confectioners’ sugar, and remaining 1/2 tsp. vanilla extract in a small bowl. Place bowl over simmering water to heat the mixture. Place the peanut butter mixture in a large pastry bag. Pipe the mixture into the depression of each cookie. Use an angled pastry knife to smooth the peanut butter over the cookie, allowing the peanut butter to be thicker in the center. Place cookies in the refrigerator for at least 1 hour.

Dip cookies in melted chocolate
Place the chocolate and shortening in a small bowl over simmering water in a double boiler. Stir to combine thoroughly. Place wax paper on a cookie sheet. Remove cookies from the refrigerator. Remove melted chocolate from the double boiler to the counter. Drop one cookie peanut butter top down into the melted chocolate. Using a fork, flip cookie over and remove from the chocolate, allow excess chocolate to drip off cookie, and place on the wax paper. Repeat until all cookies are coated. Return to the refrigerator until chocolate is set, approximately two hours.

Keep cookies refrigerated until ready to serve.

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