Using an electric mixer, beat butter and sugars until light and fluffy. In a separate bowl, sift the flour, cocoa powder, and sea salt. Add the flour mixture into the butter mixture gradually, beating on low. Finally, add the vanilla and grated chocolate, and mix until the dough is a deep brown.
I had some trouble getting the dough to homogenize with the beater, but my bare hands worked like a charm. Form dough into a flattish disk and wrap tightly with plastic wrap. Refrigerate for 30 minutes.
Preheat oven to 350º. Line baking sheet with parchment paper.
After 30 minutes, roll out the dough on the plastic wrap it was tucked into. (If the plastic wrap doesn’t provide a large enough surface, you can lightly flour another dry surface for rolling.)
Roll the dough into a 1/2” thick square. Cut dough into 1 1/2” squares using a sharp knife. You could measure them out with a ruler if you’re feeling fancy, but I was happy to go a little rogue. Place squares on parchment lined baking sheet.
Bake for 15 minutes or until firm. As soon as they come out of the oven, sprinkle each with a pinch of flaky sea salt. Cool completely.
While cooling, beat ingredients for whipped cream in a large bowl until soft peaks form, 2-3 minutes.
To form cookie sandwiches, place a dollop of whipped cream on the bottom of one cookie, drizzle liberally with caramel, and top with a second cookie. EVERYTHING.