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Step 1
After cake has cooled at least 30 minutes, take the end of a wooden spoon and poke holes throughout the top of the cake. Pour on the entire can of sweetened condensed milk.
Step 2
Combine dry pudding mix with 1/2 cup milk and whisk together. Stir in whipped topping until well combined. Add in about 1/3 of the crushed Oreos. Stir gently until everything is mixed, then spread on cake. Top with remaining crushed Oreo cookies.
Step 3
Chill for 1 hour prior to serving. Store leftovers in the refrigerator.