• You’re just a few simple steps away from a gorgeous, golden pineapple upside down cake using cake mix. Take it one stage at a time and you’ll get a perfectly moist, evenly baked cake with a glossy, caramelized topping.

Prepare the pan and topping

• Preheat your oven to 350°F (175°C).
• Lightly grease a 9-inch round cake pan, deep pie dish, or cast-iron skillet.
• Add the butter to the pan and place it in the warm oven for a few minutes until fully melted.
• Remove the pan carefully, swirl the melted butter to coat the bottom, then sprinkle the brown sugar evenly over the butter.
• Use a spoon to gently press the sugar into an even layer so the topping caramelizes nicely.
• Arrange the pineapple rings over the brown sugar in a single layer.
• Nestle a maraschino cherry into the center of each pineapple ring, and add a few extras in any gaps if you like.
• Tip: Make sure the pineapple rings sit flat. Overlapping too much can prevent the cake batter from baking evenly underneath.

Mix the cake batter

• In a large mixing bowl, add the yellow cake mix.
• Whisk in the eggs, oil, and your liquid (pineapple juice plus water or milk) according to the amounts listed in the ingredient section.
• Mix until the batter is smooth and no dry pockets remain, but avoid over-mixing—stirring just until combined helps keep your easy pineapple upside down cake soft and tender.
• Optional boost: For extra flavor, you can add a splash of vanilla extract or a pinch of cinnamon to the batter.

Combine and bake

• Slowly pour the cake batter over the arranged pineapple and cherries, starting from the center and moving outward.
• Use a spatula to gently spread the batter so it covers the fruit in an even layer.
• Tap the pan lightly on the counter a couple of times to release any large air bubbles.
• Bake in the preheated oven for about 35–45 minutes, or until:
• The top is golden and springs back lightly when touched, and
• A toothpick inserted into the cake portion (not the fruit) comes out clean or with a few moist crumbs.
• Tip: If the top is browning too quickly, tent the cake loosely with foil for the last 5–10 minutes of baking.

Cool, flip, and serve

• Once baked, remove the cake from the oven and place it on a cooling rack.
• Let it rest in the pan for about 10–15 minutes. This short cooling time allows the caramelized topping to thicken slightly but stay fluid enough to release.
• Run a thin knife around the edges of the cake to loosen it.
• Place a serving plate over the pan, then carefully and confidently flip the whole thing over in one motion.
• Leave the pan upside down on the plate for 1–2 minutes, then lift it off to reveal the caramelized pineapple topping.
• If a pineapple ring or cherry sticks to the pan, just lift it gently with a spatula and press it back into place—no one will notice. Slice your moist pineapple upside down cake while it’s still slightly warm and enjoy that buttery, fruity topping in every bite.