Pineapple Upside Down Baked Brie
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Pineapple Upside Down Baked Brie

This version of baked brie will blow your mind!


  • 6 canned pineapple rings
  • 9 maraschino cherries
  • 2 tablespoons light brown sugar divided
  • Cooking spray
  • 1 tablespoon salted butter melted
  • 1 8 ounce tube seamless crescent roll dough
  • 1 small 6-9 ounce wheel Wisconsin brie cheese


  • Place pineapple rings and maraschino cherries on folded paper towels and let stand about 10 minutes to drain excess liquid. Sprinkle pineapple slices with 1/2 tablespoon brown sugar; grill or broil until rings begin to caramelize. Set aside.

  • Heat oven to 360°F.
Spray sides of small cast iron skillet with cooking spray; add melted butter. Add remaining 1 1/2 tablespoons light brown sugar to skillet and stir until evenly combined. Place 1 pineapple ring in center of skillet and arrange remaining 5 rings around it so cast iron skillet bottom is covered. Place 1 cherry in each center hole of pineapple rings.

  • Unroll crescent dough on lightly floured or nonstick surface. Trim dough into square shape; place brie in center of square. Tightly wrap crescent dough around brie and pinch ends together to tightly seal dough.
Place brie, seam-side-down, over pineapple rings. 
  • Bake until brown sugar is bubbling and top of crescent dough is a light golden brown, about 25-35 minutes. Quickly invert brie onto plate; let sit 10-15 minutes before cutting and serving.