Pineapple Upside-down Cupcakes

Pineapple Upside-down Cupcakes - by Glorious Treats

Here I am… me, Glory, posting on my own blog for once!  Well, once out of the last couple months!  I’m so thankful to Bethany, LisaShellyDarla, Julie and Kristan for creating beautiful posts for me while I’ve been crazy busy working on my book.  Although the book will not be available until next year, then majority of my work is done, and I’m so excited to be back to my regular blog posting schedule!

I’ve wanted to share this recipe for Pineapple Upside-Down Cupcakes for quite a while!  In fact, more than once I’ve made them with the intention of taking photos… but we kind of ate them all before I had a chance!  =)

This cake is just so classic and delicious!  Feel free to make a traditional Pineapple-Upside Down Cake with the recipe, or follow the instructions to create fun individual Pineapple Upside-Down Cakes.

As I’m sure you well know, I love individual desserts.  Somehow a dessert seems extra special when each person get’s their own individual, perfect piece.   Or maybe I’m still stuck in childhood and want to make sure everyone gets a “fair” piece.

How to make Pineapple Upside-Down Cupcakes - by Glorious Treats


Print Recipe

Pineapple Upside-down Cupcakes

Yield: 12 Jumbo cupcakes, or (1) 9"x13" pan

Make this recipe using a jumbo cupcake pan for individual servings, or in a 9"x13" pan for a classic cake.


Brown Sugar Glaze
6 Tbsp. Challenge butter
2 Tbsp. light corn syrup
1 cup (packed) brown sugar

12 (canned) pineapple slices (you'll need 2 cans)
6 maraschino cherries (each cut in half)

2 1/2 cups flour
1 tsp. baking powder
1/2 tsp. baking soda
1/2 teaspoon salt
3 eggs
2 cups sugar
1 cup oil (vegetable, canola, etc)
2 tsp. vanilla extract
1 cup sour cream (any fat content)


Directions (pictured above)
1. Prepare 2 JUMBO cupcake pans by greasing the molds, and then lining just the bottoms with paper liners. I used Jumbo cupcake liners, and cut them down so the liner just fills the bottom (and up the side just a bit). The liner will just help keep the pineapple and glaze in tact as you remove the cakes from the pan.
2. Prepare the pineapple slices by cutting out a notch of pineapple (as pictured above). This allows the pineapple to sit nicely in the bottom of the cupcake pan. Cut one pineapple slice and then place it in your pan to get an idea of the size piece you need to remove.
3. Prepare the brown sugar glaze by combining the butter, corn syrup and brown sugar in a small saucepan. Heat until the butter and sugar are melted, and the mixture is smooth. Set aside to cool.
4. Prepare the cake batter. In a large bowl add the flour, baking powder, baking soda and salt. Whisk to combine, then set aside.
5. In the bowl of an electric mixer, add eggs and beat 15 seconds. Add the sugar, and continue to beat until the mixture thickens and is a light in color.
6. While mixing on low speed, add the oil and vanilla and mix until well blended. Add sour cream, and mix to combine.
7. Slowly add the flour mixture and mix just until the flour is fully incorporated.
8. Assemble cakes for baking by adding 1-1/2 tablespoons of the brown sugar mixture to the bottom of each (lined) cupcake mold. Top glaze with a slice of pineapple and half of a maraschino cherry.
9. Pour (or scoop) the cake batter on top of each pineapple slice, filling each cupcake mold 2/3 - 3/4 full (do your best to evenly divide the batter between each cupcake).
10. Bake cupcakes in a preheated 350*F oven for about 25 minutes (or until a toothpick inserted in the center of a cake comes out clean, or with a few moist crumbs).
11. Allow cakes to cool about 5 minutes, then run a knife along the edges of each cake to losen it from the pan. Flip over the entire pan, onto a baking sheet. Remove the paper liner, and serve.
Cakes can be served warm, or at room temperature.

Notes - If you only have one jumbo cupcake pan, simply bake one pan at a time, then repeat the assembly for the second batch.

If making this recipe as one large cake, lightly grease the pan, and line the bottom with parchment paper. Baking time is not listed because I have not made the recipe in a 9"x13" pan. I would estimate 45-50 minutes, but you will know the cake is done when the top is a deep golden brown, the center of the cake has a slight dome, and a toothpick inserted in the center comes out clean. After baking, cool at 15 minutes. Run a knife along the edges of the pan to loosen cake, and turn pan upside down over a baking sheet or platter. Allow the pan to remain (upside down) on the cake a minute, then carefully remove.

Recipe Source- Glorious Treats

If desired, you could prepare this recipe using the pineapple and brown sugar glaze listed, but replace the cake recipe with a boxed mix yellow cake (prepare the cake batter as directed on the box).

These beautiful and delicious little cakes can be made up to two days in advance.

Pineapple Upside-down Cupcakes - by Glorious Treats

My mom would occasionally make pineapple upside down cake when I was growing up, so the sweet and moist cake always reminds me of my childhood.  For some reason, pineapple upside down cake is one of those treats that I forget how much I like.  I often go a long time without making it, but then each time I make it,  I remember how much I love it!

When was the last time you enjoyed Pineapple Upside Down Cake?


  1. It’s a treat to have you back, Glory! Can’t wait for the book. I know it will be beautiful!

  2. Oh, how yummy! We just got our oven fixed and I cannot wait to try these! Thanks so much.

    Snoopy 😀

  3. cute and delish! thanks for sharing it with us!

  4. My mom used to make this cake too! It’s always been one of my favorite memories

  5. Yum! I have been dreaming about doing this! You have shown it can be done and done so cutely! ! ! Thanks! 🙂

  6. Hello! I have some questions! if I don’t have sour cream, what can I substitute it with? Also, if I don’t have the syrup, can I still make the glase without it? And the last one: can I use soy oil? I’m very sorry 🙁 I’m just not from USA and I can’t find some of these ingredients easily :s thank you ^^

  7. So cute! My husband love pineapple upside down cake. Might have to make these for him.

  8. this is my dad’s favorite kind of cake. Question – to half this recipe….all looks easy except for the eggs…. would you go with 1 or 2? Thanks

  9. These are so perfect for a spring cookout!! Love it!!

  10. These look great! I have to try them. We’re having a party at Tumbleweed Contessa and I’d love for you to share these with us.

    What’d You Do This Weekend?


  11. Ack! These are so ding dang cute!!

  12. I love your recipes! My favorite thing about them is they are homemade cakes and they are MOIST!! I think I will be making this for mother’s day 🙂

  13. I absolutely adore these! I need to invest in a jumbo cupcake pan!

  14. Mmm… These look delicious! I have digestive tract paralysis now, but this used to be my favorite kind of cake. I will have to make these for my family!

    Glad you’re back… Can’t wait for the cookbook!!!

  15. Welcome back! And I have made these in the same pan, they are way more fun than the 9 x 13 big cake. Just like you pineapple upside down cake holds a special place it my heart, it was the first cake that I ever baked for my husband 🙂

  16. Holey Moley.I can’t een remember how I landed here…..Oh i remember. I was googling “making fondant flowers/decorations” and lo-and-behold, I find this marvel of a thing.Pineapple upside down cake is my favourite of favourite cakes.Reminds me of my mother and I in the kitchen when I was young,, and to see individual portions? My head is spinning…….Can’t wait to get home and get started on my own litle creations…..Too beautiful and highly aesthetic………..Can you see me? Imjumping up and down.

    Well done.

  17. It looks delicious! I need to make these sooooon 😀

  18. I love pineapple. So yummy. I am really glad you are back =)

  19. This will make my hubby one happy guy! He loves pineapple upside down cake and so I will have to try this out! Love you and I miss you!


  20. What a classic! The last time I had pineapple upside down cake was when I was growing up, it was one of my mom’s favorite cakes to make.

  21. When you come over we are SOOOOOOOOOO making these! Or maybe I’ll just let you relax! 😉

  22. Thank you so much for the inspiration and recipe. I made these with a group of children with whom I volunteer. Your recipe was easy for the children to follow and the end result was both beautifully professional and delicious. We’ll be watching your site for recipes to try next month.

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  25. This recipe looks so good. I am going to use the cake portion of this recipe to make lemon cupcakes. I think the oil and sour cream are going to make for a great moist cake! Hopefully it will be my new go to recipe for vanilla cake. I am going to turn this recipe into Funfetti cupcakes with sprinkles and into strawberry lemonade cupcakes. I think I will replace the 2 tsp. of vanilla with lemon extract and add zest from two lemons. 🙂

    Glory, I have seen so many articles on measuring flour that say to use the spoon and sweep method. Do you use that method or do you scoop your flour out of the bag or container? I need to know so the recipes I see here will come out just like yours 🙂

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  27. Glory,

    Thank you so much for this amazing recipe! I made the cake portion of this recipe this past weekend and it came out great! I have found my new go to vanilla cake! Thank you so much! 🙂

  28. I made this cake as a 9×13 cake for my dad as a Fathers day gift. He loved it! Pineapple upside down cake is favorite and now I finally have a from-scratch recipe to make it for him. Thanks!

  29. Thank You so much for sharing these. I LOVE them! They were so easy to make and SOOOoooooooo DELICIOUS. The Brown Sugar Glaze is Divine and the cake batter was a piece of cake ;).

    I’m in love!…with this recipe! Thanks again.

  30. Pingback: Pineapple Upside-down Cupcakes

  31. What can I substitute for Sour Cream? I can’t buy that here! Thanks – I can’t wait to try this out!

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  33. Hi. Should I use self rise flour or all purpose flour. I’m going try the recipe today. Thanks!

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