Make the caramel filling first so that it can thicken up before being added to the cheesecake batter.
Heat 1 can of sweetened condensed milk, ½ cup butter, ½ cup packed brown sugar, ¼ cup light corn syrup, and ½ tsp fine salt over medium heat in a heavy saucepan. Stir frequently and let the mixture just begin to bubble.
Once this happens, turn the heat down to low to let the caramel simmer. Continue to stir frequently until the mixture thickens and becomes a medium caramel color (about 10 minutes). Remove from the heat and stir in 1 tsp vanilla extract.
Pour into a separate container, then set aside to cool to room temperature.
Preheat the oven to 350°F/175°C. Spray an 8- or 9-inch springform or cheesecake pan with non-stick baking spray, then place a parchment round on the bottom of the pan.
Use a fork or pastry cutter to combine ½ cup butter, 1 cup flour, ¼ cup powdered sugar, and ¼ tsp fine salt. Press into the bottom of the prepared pan with your fingers to create an even layer.
Prick the crust thoroughly with a fork, then bake for 22-25 minutes, or until the edges are just starting to brown. Place the pan on a wire rack to cool.
Keep the oven on but lower the temperature to 300°F/150°C and place a baking tray filled with about 1 inch of water on the bottom rack.
While the cookie crust bakes and cools, make the cheesecake filling. Whisk together 1 ⅓ cups of sugar and 2 Tbsp of cornstarch in a small bowl.
In a large mixing bowl or the bowl of a stand mixer fitted with a paddle attachment, beat 4, 8-oz packages of room temperature cream cheese and the sugar/cornstarch mixture on a low speed until the mixture is completely smooth.
Gradually mix the eggs into the cheesecake batter in a few installments while mixing on a low speed. Then mix in ⅔ cup sour cream, ½ cup caramel, and 1 tsp vanilla extract until just combined.
Pour the caramel cheesecake batter into the prepared pan. Double-check that the oven temperature has been lowered to 300°F/150°C, then place the cheesecake pan on a large cookie sheet and bake the cheesecake for 20 minutes.
Without opening the oven door, reduce the oven temperature to 225°F/110°C and bake for an additional 2 hours.
Once the cheesecake is done baking, turn the oven off and let the cheesecake sit in the oven for 1 hour without opening the door.
Next, remove the cheesecake from the oven and let it continue to cool at room temperature for a few hours. Once it reaches room temperature, cover the top of the cheesecake with plastic wrap and refrigerate the cheesecake for an additional 3-4 hours or overnight.
Make the chocolate ganache as the cheesecake bakes and cools. Heat ½ cup of heavy cream in a heatproof bowl in the microwave for 45 seconds.
Gently pour ⅔ cup of dark chocolate chips into the heavy cream. Let the mixture sit for 1 minute. Stir slowly until the cream and chocolate are combined and the mixture is smooth.
Mix in 2 Tbsp of unsalted butter, 1 Tbsp of corn syrup, and ¼ tsp fine salt until combined. Cover with plastic wrap to prevent the ganache from forming a skin, then set aside to cool to room temperature.
Once the cheesecake is fully cooled, carefully release it from the pan and scoop the room-temperature caramel on top of the cheesecake. Spread it into an even layer.
Chill in the fridge for 10 minutes to let the caramel firm up, then spread the room-temperature chocolate ganache on top of the caramel.
Add a sprinkle of flaky sea salt, then use a sharp, warm knife to cut into the chilled cheesecake.
