Preheat the oven to 325°F and line an 8x8 baking dish with parchment paper. In a bowl, beat 2 sticks of butter until fluffy. Mix in 1 tsp. vanilla and 1 ½ c. powdered sugar until smooth.
Add the egg, then mix in 2 ½ c. flour, for dough, and salt until a dough forms. In a separate bowl, stir together brown sugar, 2 tbsp. cinnamon, 4 tbsp. flour, for filling, 4 tbsp. melted butter, and 1 tbsp. vanilla until combined.
Press half the dough evenly into the baking dish. Spread the filling on top, then press the remaining dough over the filling. Flatten it with oiled hands if needed.
Bake for 40 minutes or until the center is set (check with a toothpick). Let the bars cool for 40 minutes.
Combine 1 c. powdered sugar, 2 tsp. cinnamon, and 3 tsp. vanilla to make the icing. Spread evenly over the cooled bars.
Let the icing set for 15 minutes (or skip if you prefer them gooey), then slice into bars and enjoy!