Pineapple Upside-Down Cupcakes {2 sizes}

August 19, 2012
Pineapple Upside-Down Cupcakes ~ The deliciousness of classic pineapple upside-down cake, in an individual cupcake size.

My Mom's birthday was a few weeks ago.  Of course, I made her a yummy birthday treat.  I can't let her special day go by without making her something special!

Last year I whipped up one of her favorites, cupcakes with coffee frosting.  Well, this year I whipped up another one of her favorites ... pineapple upside-down cake.

Well, I didn't make pineapple upside-down cake exactly.  I made Pineapple Upside-Down Cupcakes.  In 2 sizes.  Ya know, just because I could.  'Regular' cupcake tin size (pictured below), and a slightly-larger oversized cupcake baked in ramekins (pictured above).

Both sizes follow the same method, just the ones baked in ramekins come out, well ... a bit bigger.

Start by making yummy pineapple upside-down cake topping with brown sugar, butter, and some pineapple juice.

 If you'd like to make ramekin-sized cupcakes, they'll come out looking like this, with whole pineapple rings on top:

It's easy-peasy to whip up these little beauties!  Just ...

1.  Grease ramekin cups generously with butter.  This is important!! ... if you want your cupcakes to actually come out of the ramekins, that is.  I use a piece of waxed paper dipped in softened butter.

2. Spoon a couple of tablespoons of the brown sugar topping into each ramekin.

3. Drop in a whole pineapple ring.

4. Spoon cupcake vanilla cupcake batter over the pineapple ring ...
5. ... until the pineapple ring is covered and the ramekin is about 2/3 full.

6.  Bake ...

7.  ... invert ramekins on a platter ...

8.  ... and gently shake the ramekins to release the cupcakes.

Top with a cherry and VOILA! ... oversized Pineapple Upside-Down Cupcakes.

If you'd like to make regular cupcake tin-sized cupcakes, they'll come out looking like this, with pineapple tidbits on top:

Just ...

1. Grease muffin tin cups generously with butter.  Again, this is important!!

2. Spoon some of the brown sugar topping into each muffin cup.

3. Drop in a spoonful of well-drained pineapple tidbits.

4. Spoon cupcake vanilla cupcake batter over the pineapple bits.

 5.  Bake.

6.  While still warm, run a knife around the edge of each cupcake ...

7.  ... and then gently scoop each cupcake out of its muffin cup with a spoon and place inverted on a platter.

8.  A little bit of pineapple and brown sugar topping will remain behind in the pan.  No worries ... just scoop that on out and spoon it over the inverted cupcakes.
 Top with a cherry and, again, VOILA! ... regular-sized Pineapple Upside-Down Cupcakes.

Serve warm for a divinely delicious individual Pineapple Upside-Down Cupcake treat.  And if you're not planning to eat them all in one sitting, we found they were just as delicious warmed up briefly in the microwave.

So whether you choose regular-sized or oversized, you're in for a very tasty treat.
Happy birthday, Mom!

Check out these other super tasty cupcake recipes:

Pineapple Upside-Down Cupcakes
Source:  Concept from a friend, vanilla cupcakes adapted from The Hummingbird Bakery Cookbook
  • 1 (14 to 15 oz.) can pineapple tidbits or rings*, drained with juice reserved
  • 3/4 c. brown sugar
  • 2 T. butter
  • 1/8 c. pineapple juice, reserved from draining pineapple
  • 1/4 c. ground cinnamon
Vanilla Cupcakes:  (or use your favorite vanilla cupcake recipe)
  • 1 c. all-purpose flour
  • A scant 3/4 c. granulated sugar
  • 1 1/2 tsp. baking powder
  • pinch of salt
  • 3 T. butter, at room temperature
  • 1/2 c. whole milk (I've also tried it with 2% milk, and it worked fine)
  • 1 egg
  • 1 tsp. vanilla extract
  • Maraschino cherries for garnish
  1. Prepare the Topping: Combine brown sugar, butter, and pineapple juice in a small saucepan. Heat over medium heat, stirring frequently, until butter is melted and brown sugar is dissolved.
  2. Remove from heat and stir in ground cinnamon. Set aside.
  3. Prepare the Cupcake Batter: Put the flour, sugar, baking powder, salt, and butter in a mixing bowl. Beat on slow speed until everything is combined and you have a crumb mixture with a sandy consistency. Gradually pour in half of the milk; beat until the milk is just incorporated.
  4. Whisk together the remaining milk (1/4 cup), egg, and vanilla. Pour into the flour mixture and beat until all ingredients are just incorporated. Beat for about another 30 seconds to one minute until the batter is smooth. Do not over mix.
  5. Assembly & Baking: Generously grease 14 muffin cups (or some ramekins**) with butter. Spoon a scant tablespoon of brown sugar topping into each muffin cup and top with pineapple. Spoon in cupcake batter until cups are 2/3 full.
  6. Bake at 325 degrees for 20 - 25 minutes, or until light golden and the cake springs back when lightly touched. Cool slightly in the pan.
  7. Remove cupcakes from the pan. For regular-sized cupcakes: While still warm, run a knife around the edge of each cupcake. Then gently scoop each cupcake out of its muffin cup with a spoon and place inverted on a platter. Spoon any pineapple bits and brown sugar topping that remain behind in the pan over the inverted cupcakes.   {For oversized cupcakes baked in ramekins: While still warm, invert each ramekin on a platter. Let ramekins sit inverted until cupcakes release from the ramekin, or gently shake each ramekin until the cupcakes release. Remove ramekins.}
  8. Top with a maraschino cherry and serve warm.***

* I used pineapple tidbits for regular-sized cupcakes baked in muffin tins and pineapple rings for oversized cupcakes baked in ramekins. 

** The number of ramekins needed will depend on their size.  This recipe should make about 6 to 8 oversized ramekin cupcakes.

***  We found that warming these cupcakes in the microwave (for about 10 - 12 seconds) worked just great.  They were still deliciously divine when warmed up a couple of days after baking.


Please enjoy these other yummy cupcake creations from The Kitchen is My Playground ...


  1. And... they were delicious and much appreciated!

  2. These look beautiful! I'm bookmarking this for a future party. I found you via Delightfully Dowling's Mangia Monday hop :) I'm having a Meatless Monday hop this week too, if you'd like to join: I hope to see you there!!!

  3. Both versions look great! Fun idea:@)

  4. This is a family favorite. My Grandma used to make this for my Mom as a girl. Perhaps, I should surprise my Mom too! Thanks for posting!

  5. These look delicious. My grandmother often made pineapple upside down cake...the cupcake idea looks great. Going to try it! :)

  6. Yummmm! Thanks for sharing at Pin It Thursday-- I featured you

  7. Thank you so much for sharing over at Weekend Potluck (and thank you for linking back). I do love some good pineapple upside down cake - even in cupcake form! Yummy! I shared over on facebook today. Hope you had a great weekend!

    1. Well, thank you so much, Brandee! I always enjoy comin' to your party!!

  8. I'll take 4 of the ramekin sized ones please! Those are gorgeous looking! Your pictures are amazing and have me drooling! Thank you so much for sharing on Trick or Treat Tuesday!!!

  9. Such an original, delicious and pretty dessert! It was very popular on RecipeNewZ and is now featured on our Facebook page: Congratulations and have a yummy day!

  10. They look beautiful...

  11. Soooo, your gorgeous cupcakes ended up being our most-viewed recipe last week! Yay!!! So you are one of our featured recipes this Friday! Congratulations and have a wonderful weekend! ~Brandie

  12. Ooops, and I forgot to mention. Please come on over and grab your red "I was featured button" to put on your post or wherever you'd like. The code is right inside the Weekend Potluck blog post. Thank you!

  13. Love the version with the pineapple rings. It looks just like an authentic pineapple upside down cake! Great idea!!


  15. I attempted this recipe last night. The cupcakes were a BIG hit! They were absolutely delicious! My only concern is once I placed them on the platter, while still warm, the bottom(or should I say TOP) layer stuck to the platter. I thought this could be because the cupcakes were still warm, but the this afternoon when they were served the bottom layer still stuck. Is this normal? Do you have any suggestions? THANKS!

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