Pineapple Upside Down Cornbread

5 from 1 vote

Pineapple Upside Down Cornbread

This Pineapple Upside Down Cornbread is sweet, buttery, slightly smoky, and packed with caramelized pineapple and rich cherry flavor. It’s the kind of dessert that turns heads when you flip it out of the pan—and disappears just as fast once it hits the table.

Course Dessert

Cuisine American

Keyword Cast Iron, cornbread, Pellet Grill

Prep Time 10

Cook Time 1

rest time 20

Servings

Calories 405kcal

Equipment

12-inch cast iron skillet
Grill or smoker (set to 325°F)
Mixing bowl + whisk
Spatula or butter knife
Cutting board (for flipping)

Ingredients

For the Batter

2 Boxes Jiffy honey corn muffin mix
2 Large Eggs
1/3 cup Milk
1/3 cup Pineapple Juice (from the can)

For the Base & Topping

24 oz Canned Pineapple Rings
24 oz Can Cherry Pie Filling
1 stick Butter Salted
3/4 cup Light Brown Sugar

Instructions

Prepare the Cornbread Batter:
In a mixing bowl, combine the cornbread mix, eggs, milk, and pineapple juice. Whisk until smooth and lump-free, then set aside.
Prep the Cast Iron Skillet
Melt 4 tablespoons of butter and brush it generously over the bottom and sides of your skillet.
Sprinkle about 1/4 cup of brown sugar evenly across the bottom—this is what creates that caramelized, sticky topping when flipped.
Build the Layers
Arrange pineapple rings across the bottom of the skillet, covering the entire surface
Spread the cherry pie filling evenly over the pineapple layer
Pour the cornbread batter over the topFinish with a light sprinkle of brown sugar
Smoke the Cornbread
Place the skillet on your grill or smoker set to 325°F.
Cook for about 1 hour, or until the cornbread is fully set in the center. The edges should be golden and slightly pulled away from the pan.
Add the Brown Sugar Butter Glaze
While the cornbread is still hot, mix the remaining brown sugar with the melted butter and spread it evenly over the top. This step takes it from good to unforgettable.
Flip & Reveal
Let the cornbread cool for about 20 minutes—this is key.
Run a knife or spatula around the edges to loosen, then place a cutting board over the skillet and carefully flip it in one smooth motion.
Wait a few seconds before lifting the pan…then reveal that glossy, caramelized pineapple top.

Video

Notes

🔥 Pro Tips for Success

Use a well-seasoned cast iron skillet to prevent sticking
Don’t rush the cooling process before flipping
Keep your grill temperature steady at 325°F
If using a smoker, place a drip pan underneath to avoid flare-ups
For extra flavor, cook over fruit wood like apple or cherry

🍨 Serving Suggestions

This cornbread is incredible on its own—but if you want to take it over the top:

🍦 Add a scoop of vanilla ice cream
🍯 Drizzle with caramel sauce
☁️ Top with whipped cream
🥃 Pair with a bourbon cocktail or coffee

🔄 Variations & Substitutions

Want to make it your own? Try these ideas:

Swap cherry pie filling for peach or apple
Add shredded toasted coconut for a tropical twist
Use fresh pineapple instead of canned
Mix a splash of bourbon into the glaze for extra depth

Nutrition