Prepare the Peanut Butter Filling:
In a medium bowl, combine the creamy peanut butter, sifted powdered sugar, and ground cinnamon. Mix until smooth and well combined.
Portion the peanut butter mixture into 24 small dollops on a parchment-lined baking sheet.
Freeze for at least 30 minutes. This step ensures that the filling maintains its shape during baking.
Make the Chocolate Cookie Dough:
Preheat your oven to 350°F (175°C) and line baking sheets with parchment paper.
In a large bowl, whisk together the flour, Dutch process cocoa powder, baking soda, and salt until well combined.
In a separate bowl, combine the melted butter, brown sugar, and white sugar. Mix until smooth.
Add the vanilla extract and eggs, beating until well incorporated.
Gradually add the dry ingredients to the wet ingredients and mix until just combined.
Fold in 1 ¼ cups of chocolate chips, reserving the remaining ¼ cup for topping.
Let the dough rest for 10 minutes to allow the flour to fully hydrate.
Assembly:
Using a 2-tablespoon cookie scoop, portion the cookie dough.
Press your thumb halfway down into the dough to create a well.
Place one frozen peanut butter dollop into the well.
Gently press the dough around the peanut butter to completely seal it. Ensure no peanut butter is visible from the outside.
Place the filled cookie dough balls on the prepared baking sheets, spaced about 2 inches apart.
Baking:
Bake for 10-12 minutes until the edges are set but the centers are still slightly underbaked.
Press a few reserved chocolate chips onto the top of each cookie for extra visual appeal.
Let the cookies cool on the baking sheet for 5 minutes before transferring to a wire rack.