In a medium saucepan, melt granulated sugar over low heat until it transforms into a deep amber color (about 8–10 minutes). Remove from heat and whisk in unsalted butter and heavy cream until smooth.

In a large mixing bowl, whisk together all-purpose flour, Dutch process cocoa powder, baking soda, and kosher salt until blended.

Cream together unsalted butter, brown sugar, and granulated sugar on medium speed for about 2–3 minutes until light and fluffy. Gradually add eggs and vanilla extract, mixing until fully incorporated.

Slowly add the dry ingredient mixture until just combined, forming a thick cookie dough.

Fold in dark chocolate chips until evenly distributed.

Scoop portions of dough (approximately 2½ oz each), roll into balls, and press a small indentation in each ball. Freeze for at least 1 hour.

Preheat oven to 350°F (175°C). Bake frozen cookie dough balls for 8–10 minutes until edges are set but centers are soft.

Cool cookies on baking sheet for about 5 minutes, then fill each indentation with warm homemade caramel. Let cool completely.