Select a pineapple that yields slightly to pressure with a sweet aroma at the base—overripe fruit will turn mushy on the grill, while underripe won't caramelize properly.

Mix brown sugar with ground cinnamon and a pinch of salt, then press the mixture firmly onto pineapple surfaces before grilling to develop a deep caramelized crust instead of a simple coating.

Remove excess moisture from pineapple slices with paper towels before applying the glaze—this prevents steaming and allows the sugar to properly caramelize and create that coveted five-star steakhouse finish.

Place pineapple rings perpendicular to grill grates for 3-4 minutes per side, rotating 90 degrees halfway through to create beautiful crosshatch grill marks and ensure even caramelization.

Remove pineapple from direct heat when the glaze appears slightly underdone—it will continue caramelizing from residual heat, preventing burning while maximizing that perfect gooey, caramelized coating.