Ingredients
Dough
- 3⅔ cups bread flour (or 500g)
- 1 (3.3oz./93g) box instant vanilla pudding mix
- 2 teaspoons baking powder (12g)
- 1½ teaspoons ground cinnamon
- 1¼ teaspoons salt
- 1 cup unsalted butter (226g), room temperature
- 1½ cups light brown sugar (315g), packed
- 3 large eggs, room temperature
- 1½ teaspoons vanilla extract
Icing
- 4 tablespoons salted butter (55g)
- ½ cup light brown sugar (105g), packed
- 1 cup powdered sugar (125g)
- ¼ cup heavy cream
- ½ teaspoon vanilla extract
Filling & Garnish
- 36 Brown Sugar Cinnamon Pop Tart Bites (about 6 bites per bag)
Instructions
- Preheat Oven and Prepare Baking Sheets: Preheat your oven to 375°F (190°C). Line two 12×17-inch baking sheets with parchment paper and set aside to prevent sticking.
- Mix Dry Ingredients: In a large bowl, whisk together the bread flour, instant vanilla pudding mix, baking powder, ground cinnamon, and salt until well combined and set this dry mixture aside.
- Cream Butter and Sugar: In a separate large bowl or using a stand mixer fitted with a paddle attachment, cream the unsalted butter and light brown sugar together for about 1 minute until the mixture is smooth and creamy.
- Add Eggs: Add the eggs one at a time to the creamed mixture, mixing briefly after each addition just until incorporated to ensure even texture.
- Incorporate Vanilla: Add the vanilla extract and beat the mixture for 2 minutes until light, fluffy, and resembling buttercream frosting. Scrape down the bowl sides as needed to mix evenly.
- Combine Dry and Wet Ingredients: With your mixer on low speed, gradually add the dry ingredients into the wet mixture a little at a time. Continue mixing until a cohesive dough forms with a play-doh-like texture—not sticky or too wet.
- Portion Dough and Add Pop Tart Bites: Using a kitchen scale, measure 2.5-ounce (71g) portions of dough. For each portion, create a well in the center and press one Brown Sugar Cinnamon Pop Tart Bite inside, then carefully encase the pop tart fully with dough. Roll gently between palms to smooth the edges. Reserve 18 Pop Tart Bites to use later for topping.
- Arrange on Baking Sheet: Place 9 stuffed cookies evenly spaced on each prepared baking sheet, leaving about 2 inches between cookies for spreading.
- Bake: Bake the cookies one sheet at a time in the preheated oven for 8 to 10 minutes, or until the edges are set and the cookies are lightly golden.
- Cool: Remove cookies from oven and allow them to cool on the baking sheet for at least 5 minutes to firm up before transferring them to a wire rack to cool completely.
- Prepare Icing: In a small saucepan over medium-high heat, melt salted butter with light brown sugar. Bring the mixture to a boil, stirring constantly, and boil for 2 minutes to achieve a smooth caramel-like consistency.
- Mix Icing Ingredients: Remove from heat and stir in powdered sugar, heavy cream, and vanilla extract until completely smooth. Let the icing sit for 4 to 5 minutes to thicken slightly but do not let it harden.
- Ice and Garnish Cookies: Spoon about 1 tablespoon of the brown sugar icing over the top of each cooled cookie. Immediately press one reserved Pop Tart Bite onto the icing to secure it, working in small batches of about 3 cookies at a time to prevent the icing from setting before topping.
Notes
- Using bread flour adds extra chewiness and structure to the cookie dough, but all-purpose flour can substitute if needed.
- Room temperature eggs and butter ensure smooth mixing and light texture.
- Instant pudding mix in the dough keeps the cookies soft and moist.
- Weighing dough portions ensures consistently sized cookies and even baking.
- Work quickly when applying icing and Pop Tart toppings to avoid icing hardening before assembly.
- Pop Tart Bites provide an extra burst of cinnamon and sweet flavor inside and on top of the cookies.
- Store the cookies in an airtight container at room temperature for up to 3 days or refrigerate for longer freshness.
- Prep Time: 30 minutes
- Cook Time: 10 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American
