Preheat the oven to 350 degrees and line a cookie sheet with parchment paper.
Combine sugar cookie mix, softened butter, and egg in a medium-sized mixing bowl and mix well.
Add 2 tablespoons of flour and mix until a soft dough forms (dough will be crumbly).
Refrigerate dough while you make the cream cheese filling and the topping.
For the cream cheese filling, combine cream cheese, sugar, and vanilla and mix until smooth. Transfer cream cheese filling to a zippered bag and cut off the tip to pipe.
To make the crumb topping, combine graham cracker crumbs and brown sugar and set aside.
To put the cookies together, create 2 tablespoon dough balls and place them 2” apart on the prepared cooking sheet (I used a 2 tablespoon cookie scoop).
With a tablespoon, create a bowl in the middle of each cookie dough ball.
Pipe or spoon about a teaspoon of the cheesecake mixture into the cookie.
Fill the cookie with three cherries or about 2 teaspoons of cherry pie filling.
Bake for 15-17 minutes or until the edges of the cookie start to brown and the center is set.
When you remove the cookies from the oven, let them cool on the baking sheet for 10 minutes before moving them to a cooling rack.
Let cool and then drizzle with the remaining cream cheese mixture and sprinkle with the graham cracker topping.