In the bowl of your stand mixer cream together butter, brown sugar, and granulated sugar until fluffy.
Mix in the egg, vanilla, salt, and baking soda until thoroughly combined.
Add in the flour and mix until incorporated.
Form cookies into heaping tablespoon sized balls. Line a large baking sheet with plastic wrap and drop balls of dough onto the lined sheet. Using a round teaspoon press down the center of each dough ball.
Freeze for a minimum of 60 minutes.
Preheat oven to 375º F.
Spread cookies 2 inches a part on a lined baking sheet. Bake for 10 minutes (centers will slightly raise) Lightly press down the centers with the same teaspoon you used the first time. Bake for an additional 2 minutes and remove from oven to cool.
In a microwave safe bowl melt together caramels and water stirring every 30 seconds until fully melted. Fill the centers of the cookies with the caramel. Top with a pinch of the flaky salt and drizzle with melted chocolate.
Store in an airtight container. Enjoy!