Preheat the oven to 375 degrees and line a baking sheet with parchment paper.
Prepare the stuffing by bringing 1 cup water to a boil in a saucepan, then stir in the Stove Top Stuffing mix and set it aside to cool slightly.
In a mixing bowl, combine the ground beef, egg, garlic powder, and 2 tablespoons of the teriyaki sauce until evenly mixed.
Divide the meat mixture into four equal portions and flatten each into a round patty.
Place about 1/4 cup of the prepared stuffing in the center of each patty, then fold the meat around it to form a sealed mini meatloaf.
Arrange the meatloafs on the baking sheet.
Stir together the remaining teriyaki sauce, brown sugar, and 2 tablespoons of reserved pineapple juice to make the glaze.
Spoon the glaze over each meatloaf and top with the crushed pineapple.
Bake for 25 to 30 minutes until the internal temperature reaches 160 degrees.