Pineapple Upside Down Pie

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Jenna: Pineapple Upside Down Pie? 

*Legs in the air*
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Dr. Pomatter: Your hormone levels are rising beeeeautifully Mrs. Hunterson....

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This pie was a challenge. I knew it would be. Pineapple Upside Down cake, in a pie? Do I turn it into a pineapple fruit pie? With maraschino cherries? Or do I stay true to the classic cake and somehow turn it onto a crust, so it's truly upside down? I opted for the latter. And boy I am glad I did! 
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There were a few issues with my crust edges baking off, so I've altered the recipe to make those corrections!

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"Pineapple Upside Down Pie: Slices of round pineapples, bright red maraschino cherries caramelized in butter and brown sugar, baked into a vanilla cake, with a truly flaky crust baked right on top. Flipped over to turn upside down! Garnished with maraschino cherries on top. With the stem!"

You'll need 1 truly flaky crust, butter, brown sugar, canned pineapple slices, maraschino cherries, milk, sugar, shortening, vanilla extract, and baking powder. Am I missing any ingredients? Maybe. So best to see recipe below. ;)

Melt butter directly in your pie pan.

Sprinkle brown sugar over melted butter.

Lay pineapple slices atop brown sugar and butter. 

Fill the openings with maraschino cherries. I used whole cherries, and it made my cake a tad pink, I'd recommend cutting them in half or slicing them into thinner pieces before placing them in your pie tin so your caramel color is a little more brown.

Mix your cake batter...

...until smooth like this!

Gently spread cake batter over fruit...

...and keep going...

...and going... until all your batter is in the pie pan.  Smooth batter over any pieces of fruit poking out.

Lay your truly flaky crust over the batter...

...crimp up (remember you're going to flip this baby over, so the imperfections in the crimping need to be facing up so that when you turn it over the crimp facing up looks purdy! Here's my suggestion: Don't crimp to the edges to the edge of the pie pan. Crimp to the edge of the cake batter, but don't let your crimping hang off the edge of the pie pan like you would on a normal pie, or it MAYYYY (most definitely will) melt off mid bake, forcing you to piece together your crust edge for your final product...

See what I mean? It's okay, we'll salvage those bits of crust later. Let pie sit for 10mins before turning over. But don't let it cool completely or your slices of pineapple might stick to the pan!

Garnish with fresh maraschino cherry. With the stem!

It turned out better than I had hoped! Delicious vanilla cake, topped with caramelized pineapples and cherries all over a TRULY flaky crust! Mmmmm...

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Recipe for Pineapple Upside Down Pie

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Ingredients:
-1 truly flaky crust (single)
-2 TBSPN butter
-1/4 cup brown sugar
-4 slices canned pineapple slices (1 whole, 3 cut into halves)
-5 maraschino cherries (cut in halves or thirds)
-3/4 cup all-purpose flour
-1 TSPN baking powder
-1/8 TSPN salt
-3 TBSPN vegetable shortening (or butter)
-1/3 cup granulated sugar
-1 egg
-1/2 TSPN vanilla extract
-1/3 cup of whole milk

Directions:

1. Melt 2 TBSPN butter into your pie pan directly over very low heat. Be careful when taking off the stove (wear mits!)
2. Sprinkle brown sugar over the butter while butter is still warm.
3. Lay pineapple slices in a circular pattern, which whole slice in the middle, and half slices around. Place cherry slices to fill in the gaps of the pineapples. Set aside.
4. To assemble the cake batter, whip shortening and sugar together until blended, add egg, then add milk and vanilla extract.
5. Add flour, baking soda, and salt (sifted together of course) to the batter.
6. Pour cake batter over the fruit, being careful as to not mix the fruit. Smooth over top.
7. Lay truly flaky pie crust over the cake batter and crimp edges.
8. Bake at 400F for 10 mins, then reduce heat to 350F for another 15-25. You'll know the cake is down when you insert a toothpick into the middle of the pie and the toothpick comes out clean.
9. Place a large plate over the top of the pie, and flip everything over carefully. Let the pie pan stay in place over the cake for 10 mins, then remove the pie pan slowly, to reveal your Pineapple Upside Down Cake!
10. SUGAR. BUTTER. FLOUR.