Preheat oven to 350 degrees. Spray cupcake pan(s) with non-stick cooking spray. Set aside.

In a stand mixer or with a hand mixer, cream butter and sugars together until pale and fluffy, 3-4 minutes. Add the egg and vanilla, beating until well combined.

Add the dry ingredients to the wet ingredients and beat until combined and smooth. Dough will be thick. Refrigerate for 15 minutes.

Roll 2 tablespoons of dough into a ball, then press dough in bottoms of prepared cupcake cups, spreading about 1/3-1/2 way up the sides of each and forming a cup shape.

Bake for 10-12 minutes. Remove from oven and allow to cool for 5 minutes, then remove to cooling rack. Use the underside of a measuring tablespoon to press the center down if they don't fall enough.

Combine brown sugar and butter in small saucepan. Cook over medium heat, stirring constantly until mixture begins to boil. Continue cooking and stirring for about 1 minute.

Remove saucepan from heat. Whisk in whipping cream until combined. Cool 15 minutes.

Fill each cooled cookie cup halfway with the cooled caramel. Allow them to set 5 minutes. 

Place the chocolate into a medium bowl.

Heat the cream in a small sauce pan set over medium heat. Bring just to a boil, then pour it over the chopped chocolate. Allow it to sit for 3 or 4 minutes to soften before adding the vanilla, then whisking until smooth. Cool 15-20 minutes.

Spoon cooled ganache over the caramel in each cookie cup. Allow to cool 30 minutes.

Pipe domes of whipped topping on each cup, garnish with whole toasted pecan halves, then drizzle with caramel and/or ganache as desired.