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Step 1
Whisk pudding, milk, and vanilla in a medium sized bowl. Let it sit while you prepare the crust.
Step 2
Crush the cookies in a large gallon sized ziploc bag using a rolling pin. Reserve 1/2 cup of the cookie crumbs. Place the 2 tablespoons melted butter in the bag and press with your hands to work the butter through the remaining cookie crumbs. Pour crumbs into a 9” square baking dish. The crust won’t be solid, it’ll stay crumbly.
Step 3
Fold 8 ounces of the whipped topping into the pudding. Place half the pudding mixture on top of the crust. Place the strawberries in a single layer over the pudding. Spread remaining pudding mix over the top of the berries. Top with more whipped topping and sprinkle the remaining cookies over the top.
Step 4
Chill for at least 4 hours before serving.