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!
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 cornstarch, 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 8x8 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.