In a mixing bowl, combine together softened cream cheese and sugar. Beat it together with an electric mixer for 3-5 minutes or until the sugar is completely creamed.
Refrigerate cream cheese mixture for at least 2 hours.
In another mixing bowl, combine softened butter and sugar. Use a hand mixer to beat until creamed together. Ensure no clumps of butter are left.
Add canned pumpkin, vanilla extract, and the egg to the creamed butter. Beat together again until a luscious, smooth orange mixture forms.
Then, pour all of the dry ingredients into the bowl and mix together again. Use the hand mixer to ensure all of the flour is mixed in, but do not over beat.
Refrigerate cookie batter for 2 hours (or overnight).
Preheat the oven to 350°F. Grease a cookie sheet with butter or cooking spray.
Using a greased spoon (I just spray with cooking spray), drop 12 equal dollops of cookie dough onto the cookie sheet. You will need to use your fingers to shape them into an even circle after dropping them.
Create small, circular “wells” in each dollop of cookie dough. You can do this using your fingers or a small spoon for the cream cheese mixture to sit in (this is like the “thumbprint” of a thumbprint cookie, although the pumpkin batter is much wetter so it won’t be as perfect).
Then use a small spoon to scoop even amounts of cheesecake filling into the well and on the top of each cookie.
Bake for cookies for 15-18 minutes or until the edges of the cookies are lightly brown, and each cookie is a fluffy, pillow texture. Enjoy!