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Favorite Vintage Pineapple Upside Down Ham Recipe

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A nostalgic and easy-to-make pineapple upside down ham recipe featuring a caramelized brown sugar glaze and juicy pineapple rings, perfect for cozy dinners and retro vibes.

Ingredients

Scale
  • 2–3 pounds bone-in ham steak or half ham (pre-cooked)
  • 1 can (about 8 rings) canned pineapple rings
  • 1 cup (200 g) brown sugar
  • 4 tablespoons (56 g) unsalted butter, softened
  • 8–10 maraschino cherries (optional)
  • 1 teaspoon ground cinnamon
  • 1/4 teaspoon ground cloves
  • 1 tablespoon honey or maple syrup (optional)
  • Black pepper to taste

Instructions

  1. Preheat your oven to 350°F (175°C).
  2. In a mixing bowl, combine brown sugar, softened butter, ground cinnamon, ground cloves, and honey or maple syrup if using. Mix until smooth and spreadable.
  3. Place pineapple rings evenly on the bottom of a 10-12 inch cast iron skillet or oven-safe baking dish. Tuck a maraschino cherry into the center of each ring if desired.
  4. Spoon the glaze mixture evenly over and around the pineapple rings, covering the base of the pan well.
  5. Lay the bone-in ham steak or half ham on top of the glazed pineapple. Pat gently to press the glaze onto the ham’s surface.
  6. Season the ham with freshly ground black pepper.
  7. Bake uncovered for 45-55 minutes until the ham is heated through and the glaze is bubbling and caramelized. Tent with foil if the glaze darkens too quickly after 40 minutes.
  8. Let the ham rest for 10 minutes after baking to allow juices to redistribute.
  9. Carefully invert the skillet over a large plate or tray to flip the ham so the pineapple and caramelized glaze are on top.
  10. Serve warm, slicing and enjoying the sweet-savory ham.

Notes

Watch the glaze closely after 40 minutes to prevent burning; tent with foil if needed. Resting the ham after baking keeps it juicy. For dairy-free, substitute butter with coconut oil or plant-based margarine. Flipping the ham can be tricky; use a large plate and work slowly. Lining the pan with parchment paper before glazing can help release the ham easily.

Nutrition

Keywords: pineapple upside down ham, vintage ham recipe, retro dinner, brown sugar glaze, easy ham recipe, holiday ham, sweet and savory ham

Find it online: https://flurpchef.com/favorite-vintage-pineapple-upside-down-ham-recipe-easy-perfect-retro-dinner-idea/