Step 1: Prepare the Cheesecake Filling

• In a medium bowl, beat the softened cream cheese with an electric mixer until smooth and creamy.
• Add the powdered sugar, vanilla extract, and flour (if using). Mix until well combined and smooth.
• Spoon the cheesecake mixture into a piping bag or a resealable plastic bag with the corner snipped off. Place in the fridge to chill while you prepare the cookie dough.

Step 2: Make the Pumpkin Cookie Dough

• In a large bowl, cream together the softened butter, granulated sugar, and brown sugar until light and fluffy.
• Mix in the canned pumpkin puree, egg, and vanilla extract until well combined.
• In a separate bowl, whisk together the flour, baking powder, baking soda, cinnamon, nutmeg, salt, and ginger.
• Gradually add the dry ingredients to the wet ingredients, mixing until just combined. Do not overmix!

Step 3: Chill the Dough

• Cover the cookie dough with plastic wrap and refrigerate for about 30 minutes. This will help the cookies hold their shape while baking.

Step 4: Assemble the Cookies

• Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper.
• Once the dough is chilled, use a cookie scoop or tablespoon to portion out the dough onto the prepared baking sheet, spacing them about 2 inches apart.
• Using your thumb or the back of a spoon, make a small indentation in the center of each cookie dough ball.
• Remove the cheesecake filling from the fridge and pipe a small dollop into the center of each indentation.

Step 5: Bake the Cookies

• Bake the cookies in the preheated oven for 12-15 minutes, or until the edges are lightly golden.
• Let them cool on the baking sheet for 5 minutes before transferring to a wire rack to cool completely.