Pineapple Upside Down Cornbread

If you’ve ever wondered what would happen if a classic pineapple upside-down cake met Southern cornbread and took a trip through the smoker…this WILL definitely get you invited back to the next cookout!!!

Jump to Recipe

🍍Pineapple Cornbread (Smoked to Sweet Perfection)

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.

Whether you’re firing up the grill for a backyard BBQ, hosting a holiday, or just looking to try something different, this recipe delivers big flavor with minimal effort.

🔥 Why You’ll Love This Recipe

This isn’t your average cornbread—and that’s exactly the point.

• 🍍 Sweet caramelized pineapple in every bite
• 🔥 Light smoky flavor from the grill or smoker
• 🧈 Rich, buttery brown sugar glaze
• 🍒 A pop of cherry flavor that sets it apart
• 👀 Show-stopping presentation when flipped
• 👨‍👩‍👧‍👦 Perfect for feeding a crowd (10–12 servings)

🛒Ingredients

For the Cornbread Batter

• 2 boxes Jiffy honey corn muffin mix
• 2 eggs
• 1/3 cup milk
• 1/3 cup pineapple juice (from the can)

For the Base & Topping

• 24oz can pineapple rings
• 24oz can cherry pie filling
• 1 stick butter (divided)
• 3/4 cup brown sugar (divided)

🔧 Equipment You’ll Need

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

👨‍🍳 How to Make Pineapple Upside Down Cornbread

1. 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.

2. 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.

3. 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 top
• Finish with a light sprinkle of brown sugar

4. 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.

5. 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.

6. 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.

🔥 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

❓ Frequently Asked Questions

Can I make this in the oven?

Yes—bake at 325°F for about the same amount of time.

How do I keep it from sticking?

Make sure the skillet is well buttered and don’t skip loosening the edges before flipping.

Can I make this ahead of time?

Absolutely. Just reheat gently in the oven before serving.

🧊 Storage & Reheating

• Store leftovers covered in the fridge for up to 3 days
• Reheat in a 300°F oven or microwave individual slices

📣Final Tips

This Pineapple Upside Down Cornbread is one of those recipes that hits every note—sweet, buttery, smoky, and just a little unexpected. It’s easy enough for a weeknight cookout but impressive enough for a holiday table.

Once you flip it out of that skillet and see that caramelized pineapple top, you’ll know you’ve got something special.

💬 Tried It?

If you make this recipe, drop a comment below and let me know how it turned out!

And don’t forget to tag @Grilling24x7 on social media—I love seeing your creations 🔥

Sharing is caring!