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Pineapple Upside Down Cobbler for Two

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Pineapple upside down cobbler for two combines two classic desserts:  pineapple upside down cake and an easy summer cobbler!  This small batch dessert recipe combines juicy pineapple chunks and sweet maraschino cherries to make a gooey filling.  And the tender cobbler top is the best of both a buttery biscuit and sweet cake!

Gooey chunk of pineapple and cherry on a spoon in a pineapple upside down cobbler.

Everything To Love About This Pineapple Cobbler

It’s summer, which means it’s cobbler season!  And I can think of no better flavor to showcase in a cobbler than a pineapple upside down cake.  You have the sweet & sour pineapple chunks covered in caramel; delightfully sweet maraschino cherries; and the buttery soft cake – which turns into a pseudo-biscuit for the cobbler.  

All of those flavors are front and center in this cobbler recipe!

With each bite, your senses are delighted with all of the flavors and textures.  And if you close your eyes, you may actually think you’re taking a bite out of a cake!  But, what may be the pièce de résistance – the gooey, caramel filling.  

For this recipe, we grease the baking dishes with a generous portion of butter.  This bakes with the sugar and fruit juices to create a near caramel treat.  Trust me, you will be scraping the bottom of the baking dish to get every last bite!

And if I haven’t tempted you enough with this pineapple cobbler for two, I will leave you with this:  a cobbler dessert is incredibly versatile.  The sky is nearly the limit when imagining a fruity filling with biscuit topping.  Take my chocolate stone fruit cobbler and white peach cobbler as examples.  

So here’s to summer and what may be one of the easiest desserts to make!

How To Make Pineapple Cobbler for Two

1. all the cobbler ingredients

There are two components to this cobbler dessert recipe: the fruit filling and the cobbler topping.

For the filling, we take canned pineapple chunks with reserved juice, brown sugar (light or dark will work to make the caramel-like filling), corn starch to thicken the filling, a pinch of salt to balance the sweetness. And we can’t forget the maraschino cherries – which you could swap for fresh cherries.

Wet cobbler ingredients in mixing bowls on a table.

The biscuit topping for the pineapple cobbler is a cross between a crunchy biscuit and tender cake. We combine all-purpose flour with almond flour – to give the topping a little extra flavor and texture. Sugar will give just a kiss of sweetness (we don’t need too much because the filling is sweet!). Baking powder to make the topping soft. Salt for flavor. And of course, cold butter to make the cobbler top light, flavorful, and tender. We finish the topping with milk to create a thick batter.

Dry fruit dessert ingredients in measuing bowls on a table.

2. strain the pineapple – save the juice!

For this pineapple upside down cobbler, we use canned pineapple chunks. And I do recommend chunks for the simple reason they are good bite-sized pieces. Plus, we save some of the juice to make the filling jammy.

You will have some juice leftover and if you drink it straight from the bowl, I won’t judge! 🙂

Pineapple chunks in a strainer set over a mixing bowl.

3. mix the pineapple filling ingredients

To your bowl of pineapple chunks, add the reserved juice, brown sugar, corn starch, and salt. Give that a good stir then toss in your maraschino cherries. I slice mine in half for a better ratio of pineapple to cherry, but feel free to leave yours whole.

Now that you have your filling ready – yes, it’s that easy – set it aside while you make the cobbler topping.

4. whisk together the dry ingredients

Cobblers get their name from their appearance. The fruit dessert is topped with a biscuit-like topping that bakes into cobbles, like a cobbled road or path. And rather than use your traditional buttermilk biscuit, this cobbler top is a little softer and sweeter.

We start by whisking together the dry ingredients, then add the butter. The butter cubes should be cold because we want the cobbler top to stay soft and light.

Wondering what’s the best way to incorporate cold butter into flour? Use your fingers to mix! This will allow you to press the butter into flat discs and make sure each piece is coated with flour.

5. mix the cobbler top into a sandy mixture

Yes, after you mix the butter into the dry ingredients, it will look like sand! Add the milk and stir until you get a thick batter – almost like a cookie dough.

6. assemble the pineapple upside down cobbler

First and foremost, give your baking dishes a generous coating of butter. This will mix with the fruit and sugar to make the most incredible filling.

Portion the fruit fillin between your baking dishes, then dollop on scoops of cobbler topping batter. I like to use a larger cookie scoop for this to make portioning easy.

Once you have your cobbler dollops, give them a little press down with the back of the cookie scoop to get a broader coverage of topping.

6. bake the cobbler until bubbly

It is easy to tell when a cobbler is done baking: the filling will be bubbly and the cobbler top with be golden brown! For these pineapple upside down cobblers, this will take about 40 minutes.

Gooey insides and crunchy biscuit outside of a pineapple upside down cobbler in a white serving dish.

I find cobbler is best enjoyed the day it is baked and warm. You will want to let them cool for a few minutes (the filling will be hot like lava!). Add your favorite scoop of ice cream or whipped cream and let the flavor party begin!

FAQ -Pineapple Cobbler

Can I double the recipe to make a larger cobbler?

Yes! This recipe is easily doubled. You can bake the cobbler in a 9×9 inch pan, or even 9×13 casserole dish.

Where did you get the small casserole dishes?

I have linked the dishes in the recipe card.

Can I use fresh pineapple for the cobbler?

Yes! I still recommend chopping it into bite-sized chunks. And for the pineapple juice, you can swap with water.

How should I store leftovers?

Wrap tightly with plastic wrap and refrigerate for up to 3 days. Beyond that, and the biscuit topping my get too soggy.

Gooey inside of a pineapple upside down cobbler with biscuit topping.


Gooey chunk of pineapple and cherry on a spoon in a pineapple upside down cobbler.
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Pineapple Upside Down Cobbler for Two

Yield: 4 Servings
Pineapple upside down cobbler for two combines two classic desserts:  pineapple upside down cake and an easy summer cobbler!  This small batch dessert recipe combines juicy pineapple chunks and sweet maraschino cherries to make a gooey filling.  And the tender cobbler top is the best of both a buttery biscuit and sweet cake!
Prep20 minutes
Cook40 minutes
Total1 hour


Pineapple Filling

  • 1 20 ounce can pineapple chunks, drained (reserve 1/3 cup of the juice)
  • cup pineapple juice
  • 2 tablespoons brown sugar, light or dark
  • 1 tablespoon corn starch
  • 1/8 teaspoon salt
  • ¼ cup maraschino cherries (sliced in half)

Cobbler Biscuit Topping

  • ½ cup all-purpose flour
  • ¼ cup blanched almond flour
  • 2 tablespoons organic cane sugar (or granulated sugar)
  • ½ teaspoon baking powder
  • ¼ teaspoon salt
  • 2 tablespoons unsalted butter, cold and cut into cubes
  • 2 ½ tablespoons milk, cold (any kind of milk)


  • Preheat the oven to 350F degrees and adjust the oven rack to the middle position. Set the two small casserole dishes (or an baking dish) on a small baking sheet. This will make getting the cobblers in and out of the oven easy, and keeps the filling from spilling into the oven.

Pineapple Filling

  • Set a strainer over a medium mixing bowl and strain the pineapple chunks. Pour 1/3 cup of the pineapple juice back in with the pineapple. Save the remainder of the juice for smoothies!
    1 20 ounce can pineapple chunks, drained, ⅓ cup pineapple juice
  • To the pineapple, add the brown sugar, corn starch, and salt. Mix well to coat the pineapple chunks. Add the maraschino cherries and mix. Set aside while you make the topping.
    2 tablespoons brown sugar, light or dark, 1 tablespoon corn starch, 1/8 teaspoon salt, ¼ cup maraschino cherries

Cobbler Biscuit Topping

  • In a medium mixing bowl, whisk together the ap flour, almond flour, sugar, baking powder, and salt. Note – I like to use almond flour for texture and flavor. You can swap in all AP flour if you prefer.
    ½ cup all-purpose flour, ¼ cup blanched almond flour, 2 tablespoons organic cane sugar, ½ teaspoon baking powder, ¼ teaspoon salt
  • Add the butter cubes to the flour mix. Using your fingers, work the butter into the flour until you have a sandy mixture. Pour in the milk and mix with a wooden spoon until you have a thick dough – like the consistency of cookie dough.
    2 tablespoons unsalted butter, cold and cut into cubes, 2 ½ tablespoons milk, cold
  • Prepare the cobblers – Grease the casserole (baking) dishes with about a 1/2 tablespoon of butter. The butter will bake with the pineapple juice and sugar to create a syrupy mix.
  • Equally portion the cobbler filling, along with all the juices, into the baking dishes. Top with a few extra cherries if desired.
  • Using a cookie scoop or large spoon, spoon dollops of the cobbler topping on each cobbler. Gently press down so the topping covers more area.
  • Bake the cobblers for at least 40 minutes, or until the filling becomes bubbly and the cobbler biscuit topping is golden brown.
  • Cool the cobblers for about 5 to 10 minutes. Serve warm with a scoop of ice cream or whipped cream.
  • The cobblers are best enjoyed the day they are baked. For leftovers, wrap the tops tightly with plastic wrap (or cling wrap) and refrigreate for up to 3 days. I recommend re-heating leftovers in the microwave.
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  • Serving Size – This is a small batch recipe that can easily be doubled.
  • Yield – As written, the recipe will yield 2 to 4 servings.
  • Baking Dishes – You can make smaller individual cobblers by using smaller ramekins.  Or make 1 larger cobbler in a larger baking dish.   I would not recommend anything larger than 8×8 dish.
  • Cherries – To keep the classic pineapple upside down cake flavors, I use maraschino cherries.  You can swap in fresh cherries as well.
  • Storage – Cover leftover cobblers tightly with plastic wrap and refrigerate for up to 3 days.  I recommend re-heating in the microwave for a few minutes to serve leftovers warm.
Course: Dessert
Cuisine: American
Author: Erin Cernich


Calories: 242kcal | Carbohydrates: 36g | Protein: 4g | Fat: 10g | Saturated Fat: 4g | Polyunsaturated Fat: 0.3g | Monounsaturated Fat: 2g | Trans Fat: 0.2g | Cholesterol: 16mg | Sodium: 279mg | Potassium: 71mg | Fiber: 2g | Sugar: 20g | Vitamin A: 198IU | Vitamin C: 2mg | Calcium: 76mg | Iron: 1mg
Nutrition information is calculated by a third-party and should only be considered an estimate and not a guarantee.
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about the author ...

I'm Erin and I'm all about desserts - and a little bit of butter!

I've tested, written, and photographed hundreds of recipes on my website. Here you'll find the tastiest small batch gluten free and traditional desserts - all homemade, all simple, and all for you! Click here to learn more about me!

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