Crush chocolate cookies in a food processor until finely ground. Melt unsalted butter and combine with cookie crumbs to achieve a wet sand texture. Press into the base of silicone molds and chill for 30 minutes.

Beat cream cheese, powdered sugar, and vanilla extract in a mixing bowl until smooth. Gradually mix in caramel sauce until fully incorporated.

Dissolve gelatin powder in boiling hot water and stir until no lumps remain. Quickly add to the cream cheese mixture.

Slowly add heavy cream while mixing until light and fluffy, about 2-3 minutes. Pipe the cheesecake filling over the chilled crusts.

Cover with cling wrap and freeze for at least 4 hours. This helps prevent freezer odors and ensures they are set before serving.

Whip heavy cream with powdered sugar and vanilla extract until you achieve stiff peaks. Transfer to piping bag for topping.

Unmold the cheesecakes and pipe swirls of whipped cream on top. Drizzle with additional caramel sauce before serving.