Preheat oven to 350°F.
Combine 1 cup AP flour, 1/2 tsp kosher salt, and 1 tbsp white sugar in a large bowl.
Add brown butter, vanilla, and cinnamon and mix with a fork until the dough becomes sand-like.
Add an egg yolk and incorporate gently into the dough. Mix until it just comes together.
Line a 9 x 9″ baking pan with parchment paper. Press your shortbread dough evenly into the bottom of the pan. Place in fridge to chill for 30 minutes.
After chilling, bake crust for 30 minutes until evenly golden brown. Cool.
Combine 1 cup white sugar and 1/2 cup water in a large saucepan over medium-high heat.
Cook until the mixture bubbles, then turns a medium golden brown / amber color.
Remove from heat and carefully add 1/4 cup heavy cream and 2 tbsp butter.
Stir to combine and add orange zest and olive oil.
Pour caramel sauce into the bottom of your tart shell. Spread evenly with an offset spatula and let cool at room temperature.
Chop and melt chocolate in a double boiler of microwave-safe bowl. Once melted, pour on top of the caramel layer and spread evenly. Top with flaky sea salt.
Chill for at least 1-2 hours. Cut into 16 bars and serve at room temperature.