Preheat your oven to 325°F (162°C).

Combine Oreo crumbs and melted butter in a bowl, mixing until fully combined. Press about 1 tablespoon of this mixture into each cupcake liner and bake for 5 minutes. Allow them to cool before adding the filling.

Lower the oven temperature to 300°F (148°C). In a mixing bowl, beat the cream cheese, light brown sugar, and flour until smooth. Then, add in the sour cream and vanilla extract, mixing thoroughly.

Slowly add the eggs one at a time, mixing on low speed to combine. Be careful to not overmix. Fold in the chopped Rolos gently.

Spoon the cheesecake batter into the cooled crusts, filling each liner almost to the top. Bake for approximately 13 minutes, then turn off the oven and let the cheesecakes sit inside for 10 minutes with the door closed, followed by 15-20 minutes with the door cracked. Transfer them to the fridge to chill.

While the cheesecakes chill, whip the heavy cream, powdered sugar, cocoa powder, and vanilla extract until stiff peaks form. Once the cheesecakes are firm, pipe the whipped cream onto each one.

Drizzle caramel sauce and chocolate sauce on top, then finish with a halved Rolo. Serve chilled.