Preheat the oven to 375°F and line two 12x17-inch baking sheets with parchment paper and set aside.
In a large bowl, whisk together the 3⅔ cups bread flour, 1 (3.3oz.) box instant vanilla pudding mix, 2 teaspoons baking powder, 1½ teaspoons ground cinnamon, and 1¼ teaspoons salt. Set aside.
3⅔ cups bread flour, 1 (3.3oz.) box instant vanilla pudding mix, 2 teaspoons baking powder, 1¼ teaspoons salt
In a separate large bowl or stand mixer fitted with a paddle attachment, cream together 1 cup unsalted butter and 1½ cups light brown sugar for 1 minute until smooth.
1 cup unsalted butter, 1½ cups light brown sugar
Add 3 large eggs one at a time, mixing after each just until incorporated.
3 large eggs
Add 1½ teaspoons vanilla extract and mix for 2 minutes until light and fluffy (it will resemble buttercream frosting), scraping down the sides of the bowl as needed.
1½ teaspoons vanilla extract
With the mixer running on low speed, slowly add the dry ingredients a little at a time to the wet ingredients until fully incorporated. The dough should come together in a play-doh texture and not be sticky.
Immediately, measure the dough into 2.5-ounce (71g) portions of dough, using a kitchen scale for best results.
Make a well in the cookie dough and gently press 1 of the 36 Brown Sugar Cinnamon Pop Tart Bites into the center of each portion of cookie dough. Then work the dough up around the pop-tart and seal it. Gently rolling between your palms to smooth and round out the edges. Reserve 18 pop-tart bites for topping the cookies with.
Add 9 cookies to each pan with 2 inches of space between them. Bake one sheet at a time.
Bake for 8 to 10 minutes.
Remove from the oven and allow them to cool on the baking sheet for at least 5 minutes before transferring them to a wire rack to cool completely.