Prep the pineapple. Peel the fruit, remove the core, and cut into 1/2-inch rings or bite-size chunks.
Pat dry with paper towels. Dry fruit browns better and helps prevent splattering.
Heat the pan. Set a large skillet (cast iron works great) over medium to medium-high heat. Add the butter and let it melt until it starts to foam.
Start the caramel base. Sprinkle in the brown sugar and a pinch of salt. Stir until the sugar dissolves and looks glossy.
You want a smooth, bubbling mixture, not grainy piles of sugar.
Add the pineapple in a single layer. Don’t crowd the pan. If needed, work in batches. Let the fruit sit undisturbed for 2–3 minutes so it can form deep golden edges.
Flip and flavor. Turn the pieces once they have caramel color.
Add vanilla and any extras you like: a splash of rum, a squeeze of lime, a dusting of cinnamon, or a touch of ginger. Cook another 2–3 minutes.
Adjust the sauce. If it looks too thick or sticky, add a teaspoon of water to loosen it. If it’s too thin, let it bubble another minute.
You’re aiming for a shiny, syrupy glaze that coats the fruit.
Taste and finish. Try a small piece. If it needs more brightness, add another drop of lime juice or a tiny pinch of salt to sharpen the flavors.
Serve warm. Spoon over ice cream, pancakes, waffles, French toast, rice pudding, Greek yogurt, or even grilled meats. Drizzle any extra sauce on top.