Pineapple Paletas with Chiles

In a small saucepan, bring the sugar and 1/2 cup of water to a boil, stirring to dissolve the sugar. Transfer 2 tablespoons of the syrup to a medium bowl, then scrape the remaining syrup into a blender. Let cool to room temperature, about 45 minutes. Add the salt and 1 cup of the pineapple to the blender and puree until smooth. Strain through a fine-mesh sieve set over a medium bowl, pressing on the solids. Stir the lime juice into the pineapple syrup. 

Meanwhile, toss the chile and the remaining 3 cups of pineapple with the reserved 2 tablespoons of syrup. 

Divide the pineapple-chile mixture between eight 3-ounce ice pop molds and top with the pineapple syrup, leaving 1/2 inch between the filling and the top of the mold. Freeze until slightly frozen and slushy, about 45 minutes. Insert wooden ice pop sticks and freeze until solid, at least 4 hours longer or, preferably, overnight. Dip the molds in hot water for a few seconds, then unmold the paletas and serve right away.