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Bring 2 cups of water to a boil, then remove from the heat. Stir in the gelatin until completely dissolved, 1 to 2 minutes. Add 1 cup cold water, the cranberry sauce and pineapple. Mix well, ensuring you break apart any large chunks of the cranberry sauce. Pour into a 9-by-13-inch pan. Cover and place in the refrigerator until firm, 3 1/2 to 4 hours.
Beat together the cream cheese and powdered sugar with a hand mixer until smooth, about 1 minute. Add the milk and mix until completely combined. The frosting should be thick but still pourable. Carefully spread the cream cheese frosting in a thin layer over the cranberry sauce. Zest the orange directly over the frosting. Serve up in individual squares.
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