Pineapple Upside Down Cobbler for Two
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 a buttery biscuit and sweet cake!
It’s summer, which means it’s cobbler season. And I can think of no better flavor to showcase in a cobbler than pineapple, cherries, and butter! You have the sweet & sour pineapple chunks covered in caramel, delightfully sweet maraschino cherries, and the buttery soft biscuit cobbler top.
With each bite, you get all the flavors and textures. If you close your eyes, you may think you’re taking a bite out of a cake, but what may be the pièce de résistance – the gooey, caramel fruit filling.
And if I haven’t tempted you enough, 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. So here’s to summer and what may be one of the easiest desserts.
If you love pineapple, then you’ll want to try these desserts next. My recipe for individual pineapple and mango crisps features a whole lot of tropical flavors. Then there is the nostalgic pineapple dole whip – a fun frozen dessert!
See How Easy The Cobbler Is To Make
1. Strain the pineapple and save the juice! Canned pineapple is totally fine for the cobbler, and my recommendation is pineapple chunks for bite-sized pieces. You will have some juice left over and if you drink it straight from the bowl, I won’t judge. 🙂
2. To your bowl of pineapple chunks, add the reserved juice, brown sugar, cornstarch, and salt. Give that a good stir, then toss in your maraschino cherries (you can also substitute fresh 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.
3. Whisk together the dry ingredients, then add the cold butter cubes. We are making a biscuit-like cobbler top. Rather than your traditional breakfast biscuit, this one is a little softer and sweeter.
Tip! Wondering what’s the best way to incorporate cold butter into flour? Use your fingers! This will allow you to press the butter into flat discs and make sure each piece is coated with flour.
4. Mix the cobbler into a sandy mixture, then add the milk. Use a sturdy spoon to stir into a thick dough – almost like cookie dough.
5. Portion the fruit filling equally into your serving dishes, then dollop on scoops of cobbler top. Give the dough a slight press-down with the back of the scoop to ensure broad coverage! Bake until the filling is bubbly – about 40 minutes.
Serving Suggestions
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!
🍍Did you make the pineapple cobbler? Let me know in the comments below (and a star rating would be wonderful too!). Let me know what your favorite topping is – or if you just dive right in. 🙂
Pineapple Upside Down Cobbler for Two
by Erin Cernich
This recipe may contain affiliate links. See my disclosure policy.Ingredients
Pineapple Filling
- 1 20 ounce can pineapple chunks, drained (reserve 1/3 cup of the juice)
- ⅓ cup (78.86 ml) pineapple juice
- 2 tablespoons (24 g) brown sugar, light or dark
- 1 tablespoon (8 g) corn starch
- ⅛ teaspoon salt
- ¼ cup (59.15 g) maraschino cherries (sliced in half)
Cobbler Biscuit Topping
- ½ cup (62.5 g) all-purpose flour
- ¼ cup (28 g) blanched almond flour
- 2 tablespoons (24 g) organic cane sugar (or granulated sugar)
- ½ teaspoon baking powder
- ¼ teaspoon salt
- 2 tablespoons (28 g) unsalted butter, cold and cut into cubes
- 2 ½ tablespoons (36.97 ml) milk, cold (any kind of milk)
Instructions
- 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.
Notes
- Serving Size – This is a small batch recipe that can easily be doubled and baked in 1 larger 9 to 10-inch casserole dish or additional small casserole dishes.
- 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.
Nutrition Estimates
About the Author …
Hi, I’m Erin! With years of experience baking for two in my own small household, I know about the love for desserts without the leftovers. I’ve tested, written, and photographed every one of the 300+ recipes on my website. And even had some of my desserts featured on Taste of Home, The Spruce Eats, ELLE, Parade, and more! From traditional to gluten free desserts for two, I have the recipe for you.
Click here to learn more about me →
Fresh Takes From Readers