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Mini Pineapple Ring Cakes

Featured in Irresistible Desserts.

These miniature versions of the classic dessert feature caramelized pineapple and cherries on top of moist, buttery cake. All the charm of the traditional cake in perfect single servings.

Casey
Updated on Mon, 20 Jan 2025 20:06:17 GMT
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A plate of cupcakes topped with pineapple slices and maraschino cherries. Pin it
A plate of cupcakes topped with pineapple slices and maraschino cherries. | cookingwithcasey.com

I'm excited to share my favorite Pineapple Upside-Down Cupcakes recipe with you! These little treats are pure sunshine with their caramelized pineapple rings and bright cherries on top of the most tender vanilla cake. Every time I make them they bring smiles and memories of tropical vacations. They're perfect for brightening up any occasion.

A Sweet Tropical Treat

What makes these cupcakes so special is how the brown sugar caramelizes with the pineapple creating this gorgeous golden top that becomes the bottom. That sweet-tart pineapple flavor runs through the whole cupcake thanks to the juice in the batter. And those maraschino cherries add such a pretty pop of color.

What You'll Need

  • For the Topping:
    • Melted butter for that perfect caramel
    • Brown sugar that gets all golden and glossy
    • Pineapple rings cut just right to fit
    • Bright maraschino cherries for the centers
  • For the Cake:
    • Soft butter at room temperature
    • Both white and brown sugars for depth
    • Fresh eggs for richness
    • Pineapple juice for extra flavor
    • Whole milk makes them tender
    • Pure vanilla extract
    • The usual suspects: flour, baking powder, soda, and salt

Let's Start Baking

Get Ready:
Heat your oven to 350°F and grease those muffin tins really well.
Make the Magic Top:
Mix your melted butter and brown sugar, put a spoonful in each cup, then add pineapple and cherries.
Mix the Batter:
Cream your butter and sugars until fluffy, add eggs and vanilla, then alternate dry ingredients with the juices.
Fill and Bake:
Spoon batter over your pineapple rings and let them bake until golden, about 20-25 minutes.
The Big Flip:
Let them cool just 5 minutes, then flip them all at once onto your serving plate.

Serving Time

I love serving these while they're still a bit warm when that caramel is all gooey. They'll keep for a couple days but honestly they never last that long at my house.

My Best Tips

Really butter those tins well, nothing's sadder than a stuck cupcake. Fresh pineapple works beautifully if you want to skip the canned. And here's my secret - a splash of rum in the batter takes them to the next level.

A close-up of golden cupcakes topped with glazed pineapple slices and bright red cherries. Pin it
A close-up of golden cupcakes topped with glazed pineapple slices and bright red cherries. | cookingwithcasey.com

Quick Answers

  • Fresh vs Canned: Both work great, just slice fresh ones thin.
  • Make Ahead: Perfect for making the day before.
  • Best Way to Serve: Warm or room temp, they're always delicious.
  • Perfect Flip: Quick and confident, that's the key.

Frequently Asked Questions

→ Why did my topping stick to the pan?

Grease pan very well and invert while still warm. Don't let cool completely in pan.

→ Can I use fresh pineapple?

Canned works better as it's more consistent in moisture and sweetness. Fresh might be too wet.

→ How do I prevent overflow?

Only fill cups 3/4 full as batter will rise. Place pan on baking sheet just in case.

→ Can I make these ahead?

Best served same day but can be stored 2 days in airtight container. Topping may get less caramelized over time.

→ Why did my fruit float up?

Press fruit firmly into butter-sugar mixture before adding batter. Don't overfill cups.

Pineapple Upside-Down Cupcakes

Individual-sized upside-down cakes featuring caramelized pineapple rings and cherries atop tender vanilla cake. A classic dessert in cupcake form.

Prep Time
20 Minutes
Cook Time
25 Minutes
Total Time
45 Minutes
By: Casey


Difficulty: Easy

Cuisine: American

Yield: 12 Servings (12 cupcakes)

Dietary: Vegetarian

Ingredients

01 1/4 cup unsalted butter, melted.
02 1/2 cup packed brown sugar.
03 12 pineapple slices (cut to fit muffin tins).
04 12 maraschino cherries.
05 1 1/2 cups all-purpose flour.
06 1/2 cup granulated sugar.
07 1/2 cup packed brown sugar.
08 1/2 cup unsalted butter, softened.
09 2 large eggs.
10 1/2 cup pineapple juice.
11 1/4 cup milk.
12 1 teaspoon vanilla extract.
13 1 teaspoon baking powder.
14 1/2 teaspoon baking soda.
15 1/4 teaspoon salt.

Instructions

Step 01

Heat oven to 350°F (175°C).

Step 02

Grease 12-cup muffin tin well.

Step 03

Mix melted butter and brown sugar for topping.

Step 04

Divide mixture among muffin cups.

Step 05

Place pineapple and cherry in each cup.

Step 06

Cream butter and sugars until fluffy.

Step 07

Beat in eggs one at a time.

Step 08

Add vanilla extract.

Step 09

Mix dry ingredients separately.

Step 10

Alternate adding dry mix and liquids to batter.

Step 11

Spoon batter into cups, 3/4 full.

Step 12

Bake 20-25 minutes.

Step 13

Cool 5 minutes in pan.

Step 14

Invert onto baking sheet.

Step 15

Let cool completely.

Notes

  1. Classic dessert in cupcake form.
  2. Best served fresh but keeps 2 days in airtight container.

Tools You'll Need

  • 12-cup muffin tin.
  • Electric mixer.
  • Baking sheet.

Allergy Information

Please check ingredients for potential allergens and consult a health professional if in doubt.
  • Dairy (butter, milk).
  • Wheat (flour).
  • Eggs.

Nutrition Facts (Per Serving)

It is important to consider this information as approximate and not to use it as definitive health advice.
  • Calories: 285
  • Total Fat: 12 g
  • Total Carbohydrate: 42 g
  • Protein: 3 g