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Pineapple Upside-Down Pie

Recipe By: Paul Arguin
Year Submitted: 2019
Winner First Place


15 ounces flour
1 Tablespoon sugar
1 teaspoon salt
1/4 teaspoon baking powder
2 ounces cold shortening
16 Tablespoons cold butter
2 teaspoons cider vinegar
4 ounces cold water
1 egg yolk
1 Tablespoon heavy cream

5.75 pounds of fresh pineapple chunks
1 1/3 cups light brown sugar, divided
1 granny smith apple
5 tablespoons butter
Zest and juice from 1 lime
1/4 teaspoon salt
3 tablespoons minute tapioca
2 teaspoons vanilla
4 maraschino cherries


Mix flour, sugar, salt, and baking powder in bowl of food processor. Add shortening and process until well incorporated. Add butter and pulse until pea-sized nuggets of butter remain. Add water and vinegar and pulse until dough is just holding together. Divide into 2 discs. Wrap in plastic and chill in refrigerator.


Place pineapple chunks and 1/3 cup of the sugar into a large roasting pan. Place in a 400 degree oven for 1-1.5 hours until pineapple is roasted and starting to caramelize and all of the released liquid has evaporated.

While pineapple is cooking, roll out bottom crust and fit into a deep disk pie plate. Place into the refrigerator until ready to fill the pie. Roll out the top crust. Using a large round cutter, lightly press 7 circles into the dough, but don’t cut through. Using a small round cutter cut out the central holes of these pineapple ring shapes. Use a fondant impression tool or a dull butter knife to reinforce the shapes and draw radial lies inside the circles like the striations in a pineapple ring. Place the top crust in the refrigerator until ready to fill the pie.

Peel and grate the apple. Squeeze out and discard the juice. Melt and brown the butter in a large saucepan. Add the brown sugar, lime zest and juice, grated apple, and salt. Stir until combined. Stir in the minute tapioca and then the roasted pineapple. Continue to stir over medium heat until warm and just starting to bubble. Pour the filling into the prepared pie dough and place the top crust on top. Trim and crimp the edges. Chill pie in freezer for 20 minutes while preheating oven to 425F. Stir egg yolk and heavy cream together and brush over top crust. Place pie in oven on bottom rack and immediately reduce to 400F. After 15 minutes, rotate pie and cover edge with pie ring. Bake for an additional 40 minutes. When pie has cooled, slice the cherries in half and insert one half into the center of each pineapple ring.