Let's Roll Snickerdoodle Whoopie Pie Stuffed Cinnamon Roll Recipe from The Miss Cupcake

Guest recipe from The Miss Cupcake

CakeSpy Note: This was one of the entries from my "So You Wanna Be a CakeSpy?" Contest--that was too good not to share! Thanks to The Miss Cupcake for sharing the recipe.

Nothing brings families together like Pillsbury cinnamon rolls, or so they say. In this off the wall dessert, the cinnamon roll is just the overcoat to its delicious cake-like insides. Unwrap the cinnamon flesh and feast your eyes and heart upon a snickerdoodle stuffed whoopie pie. Maine, who has claimed the whoopie pie origin, has no rights to this delicious “prize inside” delight. Cookie, whoopie pie, cinnamon roll, Oh my! Mr. Doughboy, now would be a good time to get on that elliptical. *insert “snicker” here…teehhehehe*

Cinnamon Roll:

  • 1 package cinnamon rolls, icing included

  • Snickerdoodle Whoopie Pies (recipe included)


  1. Preheat oven to 350*F. Grease a small cookie sheet.

  2. Unroll cinnamon rolls. Using four cinnamon rolls per whoopie pie, place one cinnamon roll on the top of each whoopie pie, one on the bottom, and two on the sides. You will need to stretch the rolls to cover the entire whoopie pie.

  3. Bake for 18-20 minutes or until light golden brown and cooked through.

  4. Warm icing, pour over cinnamon rolls. Serve immediately

Snickerdoodle Whoopie Pies (Makes about 12 whoopie pies)

Whoopie Shell:

  • 1 Vanilla Cake Mix (I use Pillsbury)

  • Water, oil, and eggs called for on the back of the box

  • 1 cup flour

  • 1 tsp. cinnamon

  • Snickerdoodle Cookie Dough


Snickerdoodle Cookie Dough:

  • ½ cup vegetable shortening

  • 1 egg

  • ¾ cup granulated sugar

  • 1 ½ cups all-purpose flour

  • 1 tsp. cream of tartar

  • ½ tsp. baking soda

  • ¼ tsp. salt

  • 1 tsp. cinnamon

  • 1/3 cup sugar


  • 2 egg whites

  • 1 1/2 tsp. vanilla

  • 1 1/2 cup vegetable shortening

  • 1/4 cup flour

  • 2 Tbsp. milk

  • 5 cups 10x sugar



  1. Preheat oven to 350*F. Line cookie sheets with parchment paper.

  2. Prepare cookie dough by creaming shortening, egg, and sugar. In a small bowl, combine flour, cream of tartar, baking soda, and salt. Slowly add to egg mixture. Place cinnamon and sugar in a small bowl. Roll into small 1-inch balls, cover in sugar mixture, and slightly flatten. Place on cookie sheets about 2-3 inches apart.

  3. Prepare cake mix as directed on package. Add flour and cinnamon until combined and smooth. Place dough on cookie sheets (on top of each cookie dough ball) by using a large cookie scoop or two spoons.

  4. Bake for 16-18 minutes or firm to the touch and lightly golden brown. Cool for 1-2 minutes and transfer to cooling racks.

  5. While baking, prepare filling. Combine egg whites, vanilla, shortening, flour, milk and half of the sugar. Once combined, add the rest of the sugar and mix for 1-2 minutes.

  6. Pipe or spread filling between two shells.

  7. Serve immediately or cover each whoopie pie with plastic wrap.