In the bowl of a stand mixer, combine the softened butter and sugar. Cream until smooth.
Add in the egg, egg yolk and vanilla. Mix until combined.
Add in about half of the flour and mix on low speed until combined. Add in the remaining flour and mix until combined. This is a thick dough - if needed, switch out the whisk attachment to the paddle for an easier mix without bending your whisk wires.
Line your baking sheet(s) with parchment and set aside.
Portion out the dough and roll in about ping pong ball size balls. Place on the parchment lined sheets with about two inches separation between each cookie.
Using your pinky or the back of a rounded spoon, make an indentation in the center of each cookie.
Place the cookies in the fridge/freezer for about 30 minutes prior to baking to decrease spread.
Preheat the oven to 375 degrees.
Bake in the preheated oven for 12 minutes.
Remove the pan(s) from the oven. Allow to cool.
Fill the indent of each cookie with salted caramel.
Sprinkle with the flaky sea salt to garnish.