Add the crushed pineapple, sugar, and finely crushed cinnamon to a pot and warm over medium heat.
Once the filling begins to lightly simmer (don’t let it boil!), add in the cornstarch and mix it in quickly.
Let the filling simmer for about 10-12 minutes, stirring often. Remove from heat and let it cool completely while you make the pastry dough.
In a large bowl, whisk together the flour, sugar, and salt.
In a separate small bowl, mix the oil and egg together.
Use a cheese grater to quickly grate the entire stick of butter, keeping it as cold as possible through the process. Alternatively, you can chop the butter into tiny pieces.
Alternate adding the grated butter, egg mixture, and cold water to the dry ingredients, mixing each time.
Once combined, use your hands to quickly roll the dough into a log.
Cover completely and let it rest for 10 minutes in the refrigerator.
Slice the dough into 16-20 even pieces, then roll each one into a ball. Cover and place in the fridge for another 10 minutes.
Preheat the oven to 350°F, and line a large baking sheet with parchment paper.
On a well-floured surface, roll each ball of dough into a very thin disk shape, one at a time (about 6-7” in diameter).
Add about 1 to 1 1/2 Tablespoons of the pineapple filling in the center/bottom half of the rolled-out dough.
Fold the top half over to make the empanada shape, then press the edges down and roll them over or use a fork.
Place each pastelito on the baking sheet (they can fit close to each other since they won’t spread).
Once you’ve made all of the pastelitos, spray the tops with a little bit of water and quickly sprinkle with extra granulated sugar.
Bake for about 25-28 minutes.
Let cool completely, then enjoy!