Cream Butter & Sugars: In a large bowl with an electric mixer, beat softened butter, brown sugar, and granulated sugar on medium-high speed for 2 minutes until pale and creamy. Mix in vanilla extract and fine salt.
Add Flour: Gradually add flour on low speed, mixing just until a cohesive, smooth dough forms. Do not overmix.
Shape & Roll: Scoop 1-tablespoon portions of dough and roll into smooth balls. Roll each ball in finely chopped toasted pecans until evenly coated. Place 2 inches apart on parchment-lined baking sheets.
Indent & Chill: Use the rounded back of a teaspoon or your thumb to make a deep, neat well in the center of each dough ball. Chill baking sheet in refrigerator for 15 minutes to prevent spreading.
Bake: Bake at 350°F (175°C) for 12 to 14 minutes until the cookie bottoms and pecans are lightly golden. If indentations puffed up, gently re-press with the teaspoon immediately while hot. Let cool completely on the baking sheet.
Fill with Caramel & Drizzle: In a small saucepan over low heat (or microwave in 20-second bursts), melt soft caramels with heavy cream until smooth and glossy. Spoon warm caramel into each cookie well. Let set for 15 minutes. Drizzle with melted dark chocolate and sprinkle with flaky sea salt.