Halve the pineapple lengthwise, then chop into 1/2-inch (1. 25 cm) pieces.
In a large bowl, toss the pineapple with the sugar until well combined.
Let it sit (macerate) at room temperature for at least 1 hour, or cover and refrigerate for up to 4 hours to draw out the juices.
Preheat your oven to 350°F (175°C). Prepare your sweet tart crust according to its recipe, but only par-bake it. Stop after you remove the foil and pie weights, so the crust is set but not yet golden.
Let the crust cool slightly on a wire rack.
Using a colander, drain the pineapple for at least 10 minutes, making sure to reserve all the collected juice in a bowl below.
Arrange the pineapple pieces in the par-baked crust, pressing gently to fill it evenly to the edges.
Bake for about 1. 5 hours, until the crust is deeply golden brown and the fruit is softened and caramelized.
While the tart bakes, pour the reserved pineapple juice into a small saucepan.
Bring to a boil over medium heat and let it simmer, stirring occasionally, until it reduces to a thick, glossy syrup. This should take about 15 minutes.
Let the tart cool before slicing.
Serve warm or at room temperature, with the cooled pineapple syrup drizzled on top or passed at the table.
Don't rush the maceration step. Allowing the fruit to sit in the sugar for at least an hour is crucial for drawing out the juices needed to create the delicious syrup.
When reducing the fruit juice into a syrup, keep a close eye on it. It can go from syrupy to burnt very quickly in the final few minutes.
