Step 1
Preheat the oven to 350 degrees F (175 degrees C). Coat a 9-inch square baking pan with nonstick cooking spray.
Step 2
Place butter in a microwave-safe bowl and heat in the microwave until melted about 1 minute. Set aside to cool slightly.
Step 3
Separate cookies and scrape cream filling into a bowl and set aside. Place cookie wafers in a food processor and grind into fine crumbs. Transfer cookie crumbs to a large bowl.
Step 4
Add melted butter to the bowl with the cookie crumbs and stir until all crumbs are moistened. Pour mixture into the prepared pan and pat down to form an even layer.
Step 5
Bake the crust in the preheated oven until set 8 to 10 minutes. Remove from oven and allow to cool.
Step 6
Meanwhile pour condensed milk into a saucepan and add cinnamon. Stir over medium-low heat until golden brown in color 45 to 60 minutes. Quickly pour caramel over the crust in the pan. Place pan on a wire rack and let cool for 15 minutes. Move pan to the refrigerator to cool completely about 30 minutes.
Step 7
Meanwhile place a stainless steel bowl and the beaters from an electric mixer into the freezer for at least 10 minutes.
Step 8
Pour heavy cream into the chilled bowl. Add reserved cookie filling and whip on high speed until stiff peaks form. Spread whipped cream evenly over the cooled caramel layer in the pan.
Step 9
Cut into 16 squares and serve.