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Preheat oven to 350°F. Mix peanuts, sugar, butter and 1/2 teaspoon of the cinnamon in medium bowl. Remove 1/4 cup and spread on small baking sheet. Divide remaining peanut mixture among 4 (4-inch) tart pans with removable bottoms. Press firmly onto bottom and up sides of each tart pan.
Bake tart crusts and peanut mixture together for 8 minutes. Cool on wire racks.
Meanwhile, microwave chocolate milk in medium microwavable bowl on HIGH 45 seconds. Add chocolate; stir until chocolate is completely melted and mixture is smooth. Set aside.
Beat peanut butter, sweetened condensed milk, vanilla and remaining 1/2 teaspoon cinnamon in large bowl with electric mixture on medium speed until smooth. Add heavy cream; beat until soft peaks form. Spread in prepared tarts crusts. Spread chocolate mixture over top.
Refrigerate at least 1 hour or until ready to serve. Cut each tart in half. Sprinkle with toasted peanut crumble. Serve immediately.