Preheat oven to 400°F (200°C).

To prepare the filling, cook plantain in boiling water for 10 minutes, or until tender.

Drain the plantain.

Combine the cooked plantain and condensed milk in a bowl.

Mash with a potato masher until well combined.

Set the plantain filling aside.

To prepare the dough, lightly spoon flour into dry measuring cups; level with a knife.

Combine 1/2 cup flour, ice water, and vinegar, stirring with a whisk until well blended to form a slurry.

Combine 1 1/2 cups flour, powdered sugar, and salt in a bowl.

Cut in shortening with a pastry blender or 2 knives until mixture resembles coarse meal.

Add slurry, tossing with a fork until moist.

Gently press dough into a 4-inch circle on 2 lengths of heavy-duty plastic wrap; cover with additional overlapping plastic wrap.

Roll dough, still covered, into an 18 x 12-inch rectangle.

Freeze for 10 minutes, or until wrap can be easily removed.

Remove wrap; place dough on a lightly floured surface.

Cut dough into 24 circles using a 3-inch round cutter.

Place circles on a baking sheet coated with cooking spray.

Lightly moisten edges of dough with water.

Spoon 2 teaspoons of plantain mixture into each circle.

Fold dough over filling; pinch edges together to seal.

Brush the tops of dough evenly with 1 tablespoon 2% milk.

Sprinkle evenly with granulated sugar.

Bake at 400°F (200°C) for 17 minutes, or until lightly browned.

Combine the chocolate chips and 2 teaspoons 2% milk in a small bowl.

Microwave on HIGH for 30 seconds; stir until smooth.

Drizzle melted chocolate over empanaditas.

Serve warm.