Prepare the Oven and Ingredients: Set your oven to 375°F and line a baking sheet with parchment paper. Slice the smoked sausage into bite-sized rounds and arrange them evenly on the prepared pan. Place a pineapple chunk directly on top of each sausage slice, creating a stack.
Make the Glaze: In a small bowl, whisk together the pineapple juice with sweet chili sauce and teriyaki sauce until well combined. This creates a sweet-savory glaze that will caramelize beautifully during baking. Drizzle this mixture evenly over all the sausage and pineapple pieces, ensuring they're well coated.
Secure and Bake: Insert a soaked toothpick through each sausage-pineapple stack to keep everything together while baking. The pre-soaking prevents the toothpicks from burning in the oven. Bake for 20-25 minutes, or until the sauce caramelizes and the edges of the sausage turn lightly golden brown.