Bake the cake as directed on the box.
While the cake is still warm (not hot), take the end of a wooden spoon and poke holes in the cake about 1 inch apart.
FILLING - In a heat safe bowl, add the 5 tablespoons of butter, light brown sugar, ground cinnamon, vanilla extract and sweetened condensed milk. You'll whisk until all the ingredients until you have them all combined.
Place the bowl in the microwave and heat on high for 1 min, remove and stir. Heat for another minute and stir. Make sure all brown sugar clumps have been removed. If not, return to the microwave for 30 second more and stir until all lumps are removed.
Carefully ladle the butter mixture evenly over the top of the cake.
FROSTING - Using a stand mixer or a handheld mixer and a medium size mixing bowl, (on medium speed) cream the butter and cream cheese together. Scrape down the sides of the mixing bowl until fully incorporated.
Reduce mixer speed to low, then add the vanilla flavoring, half & half and the powdered sugar, a ½ cup at a time.
Return the mixer speed to medium and continue mixing until the frosting is smooth and fluffy.
Spoon all of the frosting onto the cake and smooth it out evenly with a silicone spatula or a knife.
Serve & enjoy!