Homemade Bite: Upside Down Pineapple Cake

Simple, easy, and delicious.

Upside down cakes are like movies--you get a sneak preview, but you don't know what they're like until you actually see them. That's what is so fun about making these cakes, though. You never know how you did until the very end. However, unlike movies, a plot-twist in an upside down cake is disastrous. 

That's right, you've got to be absolutely methodical when lining the bottom of the pan, or else the whole cake is ruined. Thankfully, for this cake, that's no so hard. First, the melted butter gets evenly distributed around the bottom of the pan. This gets topped by a generous sprinkling of brown sugar, which, when baked, will combine with the butter and turn into a sweet coating that surrounds the whole cake. The trickiest part of constructing the bottom layer is spacing the pineapple slices and cherries evenly, so that the cake turns out totally symmetrical. One key step in achieving this is cutting the circular pineapple slices directly in half, so that all the semi-circles are identical. This will allow you to space the slices evenly apart and create just enough room for a cherry in between each pair. Once the bottom layer is complete, the batter gets poured over the beautiful assortment of pineapple slices and cherries. Be careful when pouring, though--make sure you don't ruin all your work by pouring in the batter too aggressively, for it will move the pineapple slices.  

And voila! You have your cake. Easy enough, huh? 

Nope, not so fast. Nothing in life is that easy. Inverting the cake is actually a bit challenging. As stated in the instructions below, you'll need a springform pan to make this cake. Otherwise, it's nearly impossible to invert the cake and keep the pineapple slices in tact. Even with a springform pan, the inverting has to be done quickly and accurately. If you take your sweet time, the delicious liquid-coating that's supposed to be on top of the cake might end up on the floor. Also, when inverting, make sure to place the cake exactly where you want it. I say this because it's extremely challenging to move a cake once it's been inverted, even just an inch. Trust me, I learned the hard way that the bottom of this cake wants to stick to the place it lands. 

This cake is perfect for lazy mornings--maybe a cheer-me-up after a stressful week? Not only is it fun to look at, it's also fun to eat. The top is coated by a glorious mixture of pineapple juice, cherry juice, and brown sugar. This liquid seeps into the very top of the cake, but doesn't go too far down because the cake has rich texture (due to the yogurt in the batter). This means that the top is gently soaked while the majority of the cake remains untouched--pristine, pillow-soft, and perfectly sweet.

If you like fruity desserts, or pineapple especially, then this cake is for you. In each bite, the coating on top--which bursts with fruity goodness--alongside the fluffy cake, creates a delicious combination of flavors. So, brew a good cup of coffee, cut yourself a slice, and enjoy. You deserve it (hopefully). 


Timing: 90 minutes (includes 30 minutes of cooling)

Yield: One 9-inch cake (8-10 servings)


  • 1/2 cup unsalted butter
  • 3/4 cup light brown sugar, packed
  • one 20-ounce can pineapple slices
  • about 12 maraschino cherries
  • 1 cup all-purpose flour
  • 3/4 cup granulated sugar
  • 2 teaspoons baking powder
  • pinch salt, optional and to taste
  • 1 large egg
  • 1/2 cup buttermilk (or Powdered Buttermilk, use 2 tablespoons with the dry ingredients + 1/2 cup water added with the wet)
  • 1/3 plain Greek yogurt (sour cream may be substituted)
  • 3 tablespoons canola or vegetable oil
  • 2 teaspoons vanilla extract


  • Preheat oven to 350F.
  • In a small,  microwave-safe bowl, melt the butter, about 1 minute on high power.
  • Pour the butter into a 9-inch springform cake pan. Use your finger to run a bit of butter around the side of the pan so it's well-greased.
  • Evenly sprinkle the brown sugar over the butter.
  • Add 1 whole pineapple slice to the center of the pan.
  • Cut the remaining slices directly in half. Stagger them in a fan-like fashion going around the cake (use photos for reference). I used 12 slices.
  • Place 1 cherry in the center of the whole pineapple slice in the middle of the pan.
  • Place 1 cherry in the center cutout of all the fanned pineapple slices; set pan aside.
  • In a large bowl, whisk together flour, granulated sugar, baking powder, optional salt; set aside.
  • In a separate small bowl, whisk together the next 5 wet ingredients (through vanilla).
  • Add the wet mixture to the dry, mixing lightly with a spoon or folding with a spatula until just combined. Small lumps will be present, don't overmix or try to stir them smooth.
  • Gently turn batter out into prepared pan, being careful to not disturb the pineapple slices on the sides or bottom. Fill pan only to about 3/4-full. If you have a little extra batter, discard it rather than overfilling your pan.
  • Place pan on a cookie sheet (to catch anything that does overflow) and bake for about 40 minutes, or until center is set and not jiggly, and a toothpick inserted in the center comes out clean or with a few moist crumbs, but no batter. Only go down about 1-inch with the toothpick, not all the way to the bottom where you'll hit gooey pineapple juice.
  • Place pan on a wire rack and allow cake to cool for at least 30 minutes before inverting, slicing, and serving. You may also allow the cake to cool overnight, covered with a sheet of foil, before inverting. 

Storage Instructions: Cake will keep airtight at room temperature for up to 5 days.

Recipe adapted from: http://www.averiecooks.com/2014/03/the-best-pineapple-upside-down-cake.html

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