Step 1: Make the Chocolate Cookie Dough

1. In a large bowl, cream together the softened butter, brown sugar, and granulated sugar until light and fluffy (about 2–3 minutes).

2. Beat in the eggs, one at a time, followed by the vanilla extract.

3. In a separate bowl, whisk together the flour, cocoa powder, baking soda, and salt.

4. Gradually add the dry ingredients to the wet mixture and mix until fully combined.

5. Stir in the chocolate chips.

6. Cover and chill the dough for at least 1 hour (up to overnight) for easier handling.

Step 2: Prepare the Caramel Centers

1. If your caramels are firm, microwave them with 1 tbsp milk or cream in 10-second intervals until soft but still hold their shape.

2. Let cool slightly, then form into small balls (about ½ inch wide) if needed.

3. Keep them slightly chilled so they’re easier to work with when stuffing the dough.

Step 3: Assemble the Pillows

1. Preheat your oven to 350°F (175°C) and line baking sheets with parchment paper.

2. Scoop about 1½ tbsp of dough and flatten it into a small disc.

3. Place a caramel in the center and fold the dough around it, sealing the edges and rolling into a smooth ball.

4. Place each stuffed dough ball onto the prepared baking sheet, spaced about 2 inches apart.

Step 4: Bake and Finish

1. Bake the cookies for 10–12 minutes, until the edges are set but the centers are still soft.

2. Remove from the oven and immediately sprinkle a pinch of flaky sea salt on top of each cookie.

3. Let cookies cool on the baking sheet for 5 minutes before transferring to a wire rack.