Preheat the oven to 350 degrees F. Grease an 8-inch x 4-inch loaf pan, coat it with non-stick spray, or line it with parchment paper.
In a large bowl, whisk together sugar and butter until light and fluffy. Add the two eggs, one at a time.
Combine flour with baking powder and salt, then add half of the dry ingredients along with the pineapple syrup to the egg mixture. Gently mix, then add the remaining flour along with the milk, and stir once more. Fold in the crushed pineapple until just combined. Be cautious not to overmix the batter to avoid a dense bread.
Pour the batter into the prepared pan and bake on the middle rack for 45-55 minutes, or until set in the middle and golden brown. The bread is done when a toothpick inserted in the center comes out clean. If the top starts to brown too much, tent it with aluminum foil.
Allow the bread to rest in the pan for approximately 10 minutes, then transfer it onto a wire rack to cool.
Whisk together powdered sugar, vanilla, and pineapple syrup to create the glaze. Spread the glaze evenly over the bread.