Make the Cookie Cups

1. Preheat oven to 350°F (180°C). Spray the inside of the 8 paper pie pans well with non-stick spray so that the cookies don’t stick. Set aside.
2. Combine the flour, baking soda and salt in a medium sized bowl and set aside.
3. Cream the butter and sugars together in a large mixer bowl on medium speed until light in color and fluffy, 2-3 minutes. You should be able to see the change in color happen and know it’s ready.
4. Add the egg and mix until well combined.
5. Add the vanilla extract and mix until well combined.
6. Add the dry ingredients and mix until the dough is well combined. It will be thick. Do not over mix. Once it’s well combined, use a rubber spatula to help it come together to form a more cohesive ball.
7. Create cookie dough balls of about 6 tablespoons (105g) of cookie dough per ball. You should get 8 balls.
8. Press the cookie dough evenly into the prepared paper pie pans.
9. Place the paper pie pans on a large baking sheet and bake the cookies for 12-15 minutes, then remove from the oven to cool completely.

Make the Filling & Assemble

1. While the cookies bake and cool, make the pecan pie filling. Combine all the filling ingredients except the pecans in a saucepan. Heat over medium until it begins to boil, stirring constantly.
2. Add the pecans and allow to boil for 30 seconds, then remove from the heat and pour into a bowl.
3. Refrigerate the pecan pie filling until cool and thickened.
4. When the cookies and filling have cooled, remove each cookie from the paper pie pan.
5. Heat the pie filling in the microwave for about 30 seconds, so that it is easier to stir and scoop. Spoon about 3 tablespoons of pie filling into each cookie. You should have just enough filling.
6. Serve the cookies with the pie filling either cold or at room temperature. When cold, the filling will stay in place. When at room temperature, the filling will seep out of the cookie after you cut it or bite into it.