Pineapple Upside-Down Cupcakes

These little Pineapple Upside-Down Cupcakes are just as cute as they are delicious!  With the Easter holiday approaching, I thought back on what we used to eat at my grandma’s house for Easter dinner after church.

Pineapple Upside-Down Cupcakes

Somehow she’d always manage to throw together the BEST pineapple cake at the last minute.  It was like she didn’t even have to think about what she was doing.  It was from a box and she never read the directions or measured out any of the ingredients… but it always turned out phenomenal.  I think Grandma always timed it at the very last minute so it would be piping hot from the oven when it was time for dessert.

Pineapple Upside Down Cupcakes

I think if Grandma were here today, she’d sure enjoy these little Pineapple Upside-Down Cupcakes.  I’ve seen them around online and have always thought they were so dainty… not to mention that everyone isn’t scrambling to get a slice of cake at the same time (like it used to be at Grandma’s).

Preparing Pineapple Upside-Down Cupcakes

It all starts with putting a spoonful of a brown sugar, butter and rum mixture in the bottom of a muffin tin that has been greased or sprayed with cooking spray.

Pineapple Upside-Down Cupcakes

Then place half of a maraschino cherry in the center and surround it with pineapple tidbits.  Pour the batter over the top and bake… it’s as simple as that!

Pineapple Upside-Down Cupcakes
Prep time
Cook time
Total time
Serves: 24 cupcakes
For the topping:
  • ½ cup (1 stick) butter
  • 1 cup dark brown sugar
  • 2 teaspoons dark rum
  • 1 (20 ounce) can pineapple tidbits, reserve juice for cake mix
  • 12 maraschino cherries, sliced in half
For the cupcake batter:
  • 1 package yellow cake mix (I used Duncan Heinz Classic Yellow, 16.5 ounce mix)
  • 3 large eggs
  • ⅓ cup vegetable oil
  • Reserved pineapple juice (should yield 1 cup of juice)
  1. Preheat your oven to 350 degrees.
  2. Grease 24 muffin cups.
  3. In a small saucepan over medium heat, melt butter. Add brown sugar and rum. Bring to a slight boil and cook for approximately 2 minutes, or until thickened. Remove from heat.
  4. Spoon brown sugar mixture evenly into muffin tins. Place half of a maraschino cherry in the center of each muffin tin. Surround with pineapple tidbits.
  5. In a large bowl, beat cake mix, pineapple juice, eggs and oil on low speed for until moistened, about 30 seconds. Beat on medium speed for 2 minutes.
  6. Spoon cake batter over pineapple, filling almost to the top of each tin (mine were about ⅞ full).
  7. Bake 18-22 minutes, or until toothpick inserted in the center is removed clean.
  8. Immediately invert onto wire racks and allow to cool.

Pineapple Upside-Down Cupcakes - a cute dessert that's so EASY to make!


    • Amy @ The Blond Cook says

      Hi Helen! I’ve never tried it without using rum, but I’m thinking that since it’s such a small amount, it might not hurt to omit it. Vanilla extract might be a good alternative also. Please let me know how it turns out if you try it!

  1. Jennifer says

    Great recipe. Amounts were exactly as you posted. I might reduce butter next time. Thanks for sharing.

    • Amy @ The Blond Cook says

      Hi Linzi, someone else asked the same question in the comments and I don’t know if they tried it or not. I’ve never tried it without rum so I can’t say from personal experience. However, it is such a small amount I would try using the extract (same amount). Please let me know how it turns out! :-)

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