Preheat the oven to 350°F (175°C). Lightly grease a 9-inch springform pan with baking spray. Wrap the outside and bottom of the pan securely with aluminum foil.
Pour 2 cups of hot water into a 9×13-inch oven-safe pan and set it aside.
Combine the chocolate sandwich cookie crumbs, melted butter, and salt in a large bowl. Mix until the crumbs are evenly moistened.
Firmly press the mixture into an even layer across the bottom of the prepared springform pan. Bake for 10 minutes.
Meanwhile, beat the softened cream cheese with a handheld or stand mixer on medium speed for 1–2 minutes, until smooth and creamy.
Add the granulated sugar and beat for about 1 minute, just until incorporated.
Reduce the mixer to low. Add the eggs one at a time, mixing until each egg is incorporated before adding the next.
Add the alcohol-free vanilla flavoring, heavy cream, and flour. Mix on low just until the Rolo Cheesecake filling becomes smooth. Avoid overmixing, as incorporating too much air can encourage cracks during baking.
After removing the crust from the oven, reduce the temperature to 325°F (165°C). Place the pan containing hot water on the oven's lowest rack to create a moist baking environment.
Slowly pour the cheesecake filling over the baked chocolate cookie crust. Smooth the surface with a spatula.
Bake for 1 hour. Turn off the oven without removing the cheesecake and leave it inside for another 30 minutes as the oven gradually cools.
Transfer the cheesecake to a wire rack and cool at room temperature for about 1 hour. Remove the exterior foil, then refrigerate for at least 10 hours, preferably overnight.
Once completely chilled, carefully remove the springform ring and transfer the cheesecake to a serving platter.
Combine the dulce de leche and heavy cream in a microwave-safe bowl. Heat for approximately 45 seconds, then stir until silky and smooth.
Spread the caramel topping evenly over the chilled cheesecake, extending it toward the edges.
Decorate with whipped cream and halal-suitable chocolate-caramel candies before slicing and serving.