Prep Your Oven & Pan: Preheat your oven to 375°F (190°C). Line baking sheets with parchment paper or silicone mats. This makes cleanup a breeze!
Cream Butter & Sugars: In a large bowl, beat the softened butter, brown sugar, and granulated sugar together using an electric mixer until light and fluffy. This usually takes about 2-3 minutes.
Add Wet Ingredients: Beat in the egg, egg yolk, pumpkin puree, and vanilla extract until well combined. Don't worry if it looks a little separated at first, just keep mixing gently until incorporated.
Combine Dry Ingredients: In a separate medium bowl, whisk together the flour, baking soda, pumpkin pie spice, and salt.
Combine Wet & Dry: Gradually add the dry ingredients to the wet ingredients, mixing on low speed until just combined. Be careful not to overmix! A few streaks of flour are okay; you'll mix them in fully by hand.
Make the Cheesecake Filling: In a small bowl, beat the softened cream cheese until smooth and creamy. You can add a tablespoon of sugar and a splash of vanilla here if you like, but it's optional as the cookie is sweet enough.
Scoop the Dough: Use a cookie scoop (about 2 tablespoons) to portion the cookie dough. Roll each portion into a ball and place it on the prepared baking sheet, leaving about 2 inches between cookies.
Create the Well: Gently press the back of a spoon or your thumb into the center of each cookie dough ball to create a shallow well or indentation.
Add the Filling: Spoon or pipe a small amount of the cream cheese filling into the well of each cookie dough ball. Don't overfill!
Bake: Bake for 10-12 minutes, or until the edges of the cookies are set and lightly golden. The centers might look slightly soft, but they will continue to set as they cool.
Cool: Let the cookies cool on the baking sheet for a few minutes before transferring them to a wire rack to cool completely.
Enjoy! Try to wait until they're cool enough not to burn your tongue, then dive into pumpkin cheesecake bliss!