Prep Work: Before you begin, ensure you have parchment paper, a flat surface for rolling, and a knife. Also, preheat your oven to 375 degrees.
Flatten the Dough: Place the chocolate chip cookie dough between two sheets of parchment paper. Using a rolling pin, smush it down gently and roll it out until it's the size of a long rounded rectangle, ensuring it remains thick enough to envelop the pumpkin sugar cookies.
Line 'em Up: Once your dough is evenly flattened, line up the pumpkin sugar cookies on top, standing up in the middle, leaving a little space between each. They should be embedded slightly in the dough, but not too deep.
Chill Time: Roll the dough back into a log shape with the pumpkin sugar cookies inside. Ensure the cookies are covered entirely by the chocolate chip cookie dough. Place this in the refrigerator for about 30 minutes to firm up.
Slice and Bake: After the chilling time, remove the dough from the fridge and start slicing cookies, A sharp knife works (please supervise or do this step for your child if making with kids). This is the most dificult step in terms of slicing exactly where the cookies are in between the chocolate chip dough. However, I found that once you get the first couple of cookies, you generally can sense where to slice.
Place the slices on a baking tray lined with parchment paper, ensuring they are spaced out. These cookies WILL spread so put no more than 6 on a baking pan spaced well apart.
Baking Magic: Bake the cookies in a preheated 375 degree oven for about 12-14 minutes until the edges are slightly brown. Rotate the pan in between baking.
Cool and Enjoy: Allow the cookies to cool on the baking tray for a few minutes, then transfer to a cooling rack. Once cooled, enjoy your delightful cookie-in-a-cookie!
