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Position rack in upper third of oven; preheat to 375°F. Line a large baking sheet with parchment paper.
Cut off the top and bottom of the pineapple and remove the skin with a sharp knife. Cut the pineapple in quarters lengthwise through the core. Cut out the core. (Reserve half the pineapple for another use.) Cut 2 of the pieces in half again lengthwise, then cut those 4 pieces crosswise into 6 equal pieces to make 24 chunks. Cut each slice of prosciutto lengthwise into 3 strips. Cut each strip in half crosswise to make 24 pieces total. Wrap a piece of prosciutto around each chunk of pineapple. Place on the prepared baking sheet.
Bake on the upper rack until the prosciutto is sizzling and browned in spots, 15 to 20 minutes.
Meanwhile, whisk pineapple juice, ketchup, vinegar, cornstarch and garlic powder in a small bowl. Heat oil in a small saucepan over medium heat. Add jalapeño and cook, stirring, for 1 minute. Add the juice mixture; bring to a simmer. Cook until glossy and thickened, 1 to 2 minutes. Serve the pineapple bites on toothpicks with the dipping sauce.