Begin by melting butter in a non-stick skillet or ovenproof pan over medium heat. Once melted, sprinkle the brown sugar evenly across the surface, stirring gently until the mixture bubbles and turns a rich golden color.
Arrange pineapple slices in a neat, overlapping pattern over the caramel, pressing them gently into the sugar mixture so they sit flat and snug.
Place a maraschino cherry in the center of each pineapple ring for a pop of color and sweetness.
In a mixing bowl, whisk together eggs, vanilla extract, cinnamon (if using), and salt until well combined.
In a separate bowl, sift the flour and gradually add the granulated sugar, then pour in the melted butter. Mix until just combined to form a smooth batter.
Pour the batter evenly over the pineapple slices and cherries, spreading gently with a spatula to fill all gaps.
Transfer the skillet or pan to a preheated oven at 350°F (175°C) and bake for about 40 minutes, or until the top is golden and a toothpick inserted into the center comes out clean.
Once baked, remove the cake from the oven and let it rest for 5 minutes. Then, carefully invert it onto a serving plate, so the caramelized fruit side is on top.
Gently lift the skillet or pan away, revealing a glossy, caramel-coated top with vibrant pineapple and cherry accents.
Serve slices warm or at room temperature, enjoying the soft crumb paired with the rich caramel and sweet fruit.
