Pineapple upside-down cake is one of my favorite kinds of cake. I have fond memories of enjoying the box-mix version throughout childhood but decided to attempt one from scratch once I got to college and had my own kitchen. The cakes made back then tasted great and looked pretty good, too. I had never perfected my recipe until last weekend when I made this one. Then I made it even better by adding rum! The pineapple flavor in this cake is delicate and perfectly complemented by a generous hint of spiced dark rum. In addition to the rum flavor, the presentation of this tipsy pineapple upside-down rum cake is what sets it apart. There are a few different methods of layering the fruit in a bundt cake but this is the prettiest, in my opinion.
A bundt cake takes a little longer to bake than, say, a sheet cake but the result is undeniably gorgeous. This is the showstopper you want to serve a dinner party or impress with at the bake sale…the adult bake sale, of course. As far as the boozy-infusion, there are just a couple of extra steps to make this magic: poke the baked cake with holes all over then return it to the pan and slowly pour on a rum butter glaze.
The cake will soak up all of that boozy goodness and be even better tasting for it. Voila! Tipsy Pineapple Upside-Down Rum Cake. The glaze is comprised of melted butter, sugar, pineapple juice, and, of course, dark spiced rum. Don’t worry, the finished product is moist without being soggy
This is a grown and sexy cake, meaning the rum is NOT really cooked out of it so it isn’t necessarily family friendly. But, if you know me, you know I’m usually cooking for adults! You might also know that I love supporting companies that are local, small, minority-owned, and/or woman-owned. Texas Pure-Milling makes high-quality traditional flours and baking mixes with local ingredients in support of Texas farmers and, after receiving a few of their products, I decided to try out the all-purpose flour in this recipe. It worked very well and I plan to try one of the baking mixes next to stay tuned for that.
If you follow me on Instagram, you know I was on a baking and drink-making spree this past Saturday! We are in the thick of cherry season and I am testing cherry recipes of all types. I have pounds and pounds of cherries to work with so I would love to hear from y’all about what you want me to make. Let me know in the comments below if you have ideas.
If you like boozy cakes, check out my Naked Bourbon Carrot Cake and if you want more pineapple, here’s my Pineapple Pound Cake. Thanks for reading!
In partnership with Texas Pure Milling. As always, all opinions are my own.
- 1/2 cup milk
- 3/4 cup butter melted
- 2 cups all-purpose flour
- 1 tablespoon baking powder
- 1/2 teaspoon sea salt
- 1 cup brown sugar packed
- 3 large eggs
- 2 teaspoons vanilla extract
- 1/4 cup pineapple juice
- 1/3 cup butter melted
- 1/2 cup spiced dark rum
- 1/2 cup sugar
- 1 can sliced pineapples and juice cut slices into half circles
- 10 ounce jar of maraschino cherries
- 3/4 cup brown sugar
- 1/2 cup butter
- Preheat oven to 350 degrees. Add butter from topping ingredients into bundt pan and place in oven to melt for a couple of minutes.
Meanwhile, add flour, sea salt, and baking powder to a bowl and whisk to combine. In another bowl, combine 1/2 cup pineapple juice from the can of slices, milk, butter, brown sugar, vanilla, and egg and mix until uniform.
Add wet mixture to dry and stir until batter is uniform and no dry pockets remain. Set aside.
Carefully remove pan of melted butter from oven and mix in brown sugar to create the topping. Arrange pineapple slices and cherries in pan as shown. Carefully pour cake batter over top.
Place in oven and bake for 45-50 minutes or until a toothpick inserted into multiple parts of the cake comes out clean. Remove cake from oven and let sit for about 10 minutes then invert onto a platter and poke small all over the top and sides with a skewer or toothpick.
Combine rum syrup ingredients in a small bowl and mix vigorously until uniform. Place cake back in pan and poke more holes into bottom of cake. Slowly pour rum syrup into the holes and allow cake to soak for about an hour before flipping again and serving.
That is the prettiest presentation of an upside down cake I’ve ever seen! Great job. Can’t wait to try this recipe 🙂
Thanks so much! I hope you love it.
Can you use a cake mix?
Hi, Deb! I think a cake mix could work, however, I have not tested this recipe with one so can’t speak to exactly how it would turn out. Do let me know if it works for you!
That’s such a pretty cake. I love making pineapple upside down cake but have never tried it with rum. Sounds like a tasty addition. I am going to try it.
Thanks Jazz. I’m a 60 year old bloke in UK & who took up baking during Lockdown. This recipe was a breeze & outcome delicious. Deviated by using fresh pineapple soaked in MountGay rum & sugar & baked in the oven (A delicouus dessert in it’s own right). This softens & flavours the pineapple & makes pudding even more tipsy.
Took to family meal & showered with praise. Special occasions only as broke a calculator counting the calories.
Thanks so much for your feedback, Neil. So glad you enjoyed this cake and were able to make it your own.
So fun and delightful! Upside-down BUNDT cake — love this. It slices nicely too, looks like, which isn’t true of a traditional pineapple upside down cake — you’re trapped by the pineapple rings!. And that glaze…..mmmmmm. Cherry recipes: WELL: I have never made clafoutis and am curious about it. I also wonder if it’s possible to candy fresh cherries for fruit cakes. Yes I love and make fruitcake and wonder if there’s a homemade candied cherry hack.
I love pineapple upside down cake and I am sure this one is delicious 🙂
Girl, this looks amazing! I once made mini pineapple upside down cakes… they looked nothing like this 😛 😛
This is super yummy looking! I would love to try this!
My first time trying this as a bundt and I hope my coworkers like the glaze! Thanks for the recipe 😊
You’re so welcome! I hope you all enjoy it.
I LOVE how you put the slices of pineapple in the cake as little dividers. So pleasing to look at.
Thanks, Felicia! I never thought of them that way but I have used them as guides for slices lol.
This reminds me of my grandmother’s version. So pretty!
What a compliment! Thanks for stopping by.
This is such a perfect summer dessert!
I’m a sucker for pineapple upside down cake, always have been! I love that this is a grown, sexy cake! My hubby will love this! Thank you!
my mouth is watering! What a perfect dessert for this weekend 🙂
Beautiful job!!
Thanks, Stephanie!
Yum! this is brilliant
Wow, this cake is beautiful! I love how you tucked the pineapples inside the cake batter and adding rum of course makes it even better! Definitely wanna try this!
Jazzmine, this cake looks SUPER moist and so glad to hear you’ve upgraded from the box version to making your own from scratch. Good job!
what a unique and create way to present upside down cake – I love it
Wow this is absolutely stunning! I have never seen pineapple upside down cake this way. This is my childhood favorite so I’m in love.
Thanks, Michelle! It’s a childhood favorite of mine, as well, and I wanted to change up the presentation a bit–especially because this has rum in it. 🙂
Welp, there goes my diet! This is simply gorgeous Jazz! I’m not a baker per say, but I will be finding someone to make this for me!!!
I bet you could pull this off, Aaron. Thanks for stopping by!
I made this a few days ago for my guys special birthday dinner. His favorite cake is pineapple upside-down cake and he loves dark liquor. Sounded like a win! Let me first say that I LOVE to cook but I only bake homemade desserts about 2-3x a year. Also my oven temp is not calibrates at all so I was EXTREMELY nervous!! Guys…this…cake. ((Heart Eyes)) It turned out SO beautiful!!! My only issue was that after I added the rum syrup, I placed the cake in the fridge (still in the pan) overnight. When I served it the next day, the top half was overly saturated (borderline gross) and the other half was much drier. I’m hoping that if I flip the cake over after and hour that it will rectify that problem. That being said, I am DEFINITELY making this recipe again. Thanks so much for this recipe!
Awwww, thanks Sabrina! I’m so glad this cake looked beautiful. I would say that the butter in the rum butter syrup sank to the bottom and congealed while in the fridge overnight. Flipping and serving after just an hour or so should yield the same results from the recipe. Hope it turns out perfectly for you next time!
With rum cakes you have to add the rum butter glaze while it is still warm. Even room temp and it doesn’t absorb into the cake. I also pour small amounts of the syrup over the cake at a time so the bottom of the cake can absorb some rum before it comes out of the pan. Honestly, I have never placed a rum cake in the fridge. It never lasts long enough.
Hello i was lookong to make this and had a question. Should you let the cake cool before you put it back in the pan for the rum glaze?
Hi, Naz–great question! No need to let the cake cool before adding the rum glaze.
Are you able to use this recipe in a 9inch springform pan?
Hi, Lindsey! I haven’t tested this recipe in a springform pan so I can’t speak from experience but it should work, bearing in mind that a 9-inch springform capacity is about 10 cups of batter whereas the bundt pan is about 12 cups so you might have so excess batter left over. I would also start checking for doneness after 35 minutes to be safe. Hope this is helpful!
This looks great. One question though. Does anybody have any idea how you mix softened butter into liquid ingredients?
Hi, Michael. You can combine the liquid ingredients by either whisking vigorously by hand or using a stand or hand mixer on medium speed. Alternatively, you can use melted butter instead of softened butter for an easier time mixing.
I made it tonight …. waiting for the hour to pass by so I can try it…. simple recipe, thank you!
You’re so welcome! I hope you love it.
Making this for my son’s 21st birthday tomorrow. Never made it with rum but I’m sure it will be yummy.
Thanks for reading, Cheri! Let me know how it turns out for you and if you have any questions along the way.
Do I us light brown sugar or dark brown sugar? Thanks
Hi, Marshall! I typically use light brown sugar but either will work.
Excellent -and- gorgeous. I made it exactly as described with a couple of changes. I used black rum (Goslings or Cruzan Black) and it was worth the money. For the syrup that tops it I measured the liquids and the sugars for the syrup at the beginning and stirred every so often. By doing this by the time it was time to drizzle, the sugar was 100% dissolved so I just added the melted butter and I was ready to roll. I had a lot of cherries so I added two between each pineapple slice. This was definitely a keeper!
I made this cake according to directions. It looked great going out of the oven but after adding al the glaze it is totally soaked and I would be embarrassed to serve it. It is also way too sweet. I think it would have been better to just poke holes and pour the rum on, What went wrong?
Hi, Shirley! As you said you made the cake according to directions, I’m not sure what could have gone wrong. Assuming by “soaked” you mean the texture is too wet for your liking? This cake should be far more moist than a standard cake but as written, this recipe yields a cake that would hold the rum glaze and present beautifully without seepage. As for it being too sweet for you, everyone has different preferences so I’d recommend using less sugar in the cake batter should you decide to make it again.
Just taken up Lockdown baking at ripe old age of 60 & bought a Bundt tin for this. Amazingly simple & astonishingly delicious. Hardest part getting pineapple slices to remain erect. Made a slight modification by baking fresh pineapple slices soaked in golden rum & granulated sugar mix first. ( This is probably why I couldn’t get them to stand up). Took to a family party & was showered with praise.did however wear out 3 calculators counting calorific content.
Taste and texture are amazing and delicious. Issue I have was with the recipe are the instructions. When combining all the wet ingredients, the butter would not melt and become uniform with the milk and pineapple juice. I spent wasted time trying to warm the entire mixture which was very frustrating. I would suggest that you combine the sugar, eggs and butter together separately, then add the other cold ingredients (milk and pineapple juice). This would help meld everything better.
Thanks for this feedback, Greg. I’ll add a note to the recipe regarding the butter. Glad you enjoyed the cake!