Line an 8x8 inch pan with parchment paper and lightly spray with cooking spray. Set aside!
In a large saucepan, compine sugar, butter, and milk. Once the butter has melted, bring to a boil and stir constantly for 5 minutes.
Remove from heat and stir in marshmallow fluff, chocolate chips, and vanilla. It will be thick. Lastly stir in coarse oreo crumbs until incorporated. Spread in the prepared pan and garnish the top with the chopped oreo pieces. Let cool until firm and cut into small squares.