Pineapple Upside Down Cinnamon Rolls

Pineapple Upside Down Cinnamon Rolls-001

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You may have heard me say more than once that I lov(ed) Twinkies and Ho Ho’s and the like. basically, if it was Hostess, I was there, preservatives or not. I like to delude myself by saying that with all the Hostess cakes I’ve eaten in my life, I should have enough preservatives in me to live to be 400. So when Hostess went bankrupt, I was devastated. I held candlelight vigils every night for a month and still wear the “hair” shirt I made out of old ho ho wrappers.

So when I heard Hostess was coming back in July (bought by some company or another) I stopped the candle light vigils, bought a helicopter and had it flying a “Twinkies are coming back!” banner behind it and knitted a throw rug with a Ding Dong design in the middle.

One of the things I sheepishly admit to liking from them was their packs of cinnamon rolls. That slick icing you could pull off in one horrifyingly large piece, the somewhat dry rolls (especially once you pulled off and ate the vaguely plastic icing)… it was all high on my list of “I have no idea why I like this, but I do” foods, along with gummi candies, combos, liverwurst and lemonheads.

But even I’m not totally delusional. I know that homemade cinnamon rolls are better. And YOU all know ME.  I can’t leave well enough alone and just make something the normal way. I’m genetically mutated and must screw around with a recipe. So I made Pineapple Upside Down Cinnamon Rolls. I had seen the recipe originally in a cookbook and it intrigued me. Well, intrigued was all it could do. The recipe totally sucked.  The dough was soupy and even after adding a couple extra cups of bread flour, was far too sticky to work with and I knew if I kept going, i’d 1) waste more ingredients and 2) even if I got decent textured dough, it would end up overworked. So I tossed it and started over with my tried and true recipe for sweet roll dough from The Fannie Farmer Baking Book, just updated a bit for a stand mixer. Then I made the same type of topping I put on a upside down cake, just different ratios and Bobs your uncle… Pineapple Upside Down Cinnamon Rolls. These are a wonderfully flavored tender yeast roll with a delicious cinnamony/ buttery filing then topped with a buttery/sugary/pineappley (lots of y’s here) topping. Basically, you get two desserts in one for the calories of one dessert PLUS you can feel all self righteous if you have this for breakfast. This is a longer recipe but it comes together fairly quickly and it’s definitely worth the time

You know the drill…

Pineapple Upside Down Cinnamon Rolls

  • Cinnamon Rolls-
  • 2 packages dry yeast
  • 1/4 cup warm water
  • 1 cup milk, warmed
  • 1/2 cup sugar
  • 2 teaspoons salt
  • 1/2 cup unsalted butter, room temp
  • 3 eggs, warmed up in a bowl of warm water
  • 51/4 to 51/2 cups flour
  • Filling-
  • 1 stick unsalted butter, very soft but not melted
  • 1 cup sugar
  • 2 tablespoons cinnamon
  • Topping-
  • 2 20 ounce cans pineapple chunks in juice, well drained
  • 2 sticks unsalted butter
  • 1 1/3 cups dark brown sugar
  • 1 small jar maraschino cherries, drained (optional)
  1. Sprinkle the yeast over the warm water in a small bowl. Stir and let sit for a few minutes so yeast can dissolve.
  2. Combine the milk, sugar, salt and butter in the bowl of a stand mixer and beat will. Stir in the dissolved yeast. Put on the dough hook- add 2 1/2 cups of the flour and beat until the dough comes together in a shaggy mass. Add another 2 1/2 cups flour and on low speed, mix until the dough is smooth and firm.
  3. Feel it with your fingers and if it is tacky (unless your house is very humid, 5 cups should be fine. The original ingredients were for a hand mixer. A stand mixes better and you can usually use a touch less flour to get a good dough.) add about another 1/4 cup flour. Mix at low speed for about 5 minutes. Turn the dough out into a greased bowl; turn the dough to make sure all sides get greased, then cover with plastic and set aside. Let rise until doubled in bulk.
  4. Meanwhile, make your topping and filling. For the filling, in a small bowl, combine the one cup sugar and 2 tablespoons cinnamon. Set aside.
  5. For the topping, combine the butter and brown sugar in a medium saucepan. Bring to a simmer over medium heat, stirring occasionally to mix the sugar. Add the drained pineapple, stir and simmer over medium heat for five minutes. Mixture will seem thin but it will thicken and caramelize as it cooks in the oven.
  6. Grease a 13×9 inch baking pan and preheat oven to 350 degrees. Pour the topping in and make sure to spread the pineapple out to cover the bottom of the pan. If using cherries, randomly top the pineapple mixture with some cherries.
  7. When dough has risen to double it’s original bulk, punch down. Turn out onto a floured board and knead lightly for a minute or so. Roll out into a rectangle of approximately 28 by 12 inches. It doesn’t have to be perfect.
  8. Spread the top of the dough with the very soft butter, Then sprinkle with the cinnamon/sugar mixture. Starting from one of the long sides, roll up tightly like a long jelly roll. Cut the dough into 15 pieces and lay each piece into the prepared pan. You should have the five rows of 3 rolls. Cover lightly with plastic or a damp towel and set aside to rise again. Let rise for about another half hour or until almost doubled in bulk.
  9. Bake at 350 degrees until the rolls are puffy and golden.
  10. Let sit for five minutes then invert pan over either some sheets of foil or a larger pan if you have one. Let excess topping drip down for a minute.
  11. Serve warm… cold…room temp… in a cave… on a horse…eat them any way, Sam I am.

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4 thoughts on “Pineapple Upside Down Cinnamon Rolls

  1. I remember we would spread butter or margarine on those cinnamon rolls. Talk about adding insult to injury.

    • I don’t remember that. Must have just been you and San doing that. I’m far too healthy of an eater to do that *watches my nose grow*

    • But then, between the two of us, everyone we know would weight 500 pounds. Including us. 😀 And I DID live in Texas once! I lived in Houston for a year back in the 80’s 😀

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