In a large resealable plastic bag, combine peppers, onion and 1-1/2 cups Italian dressing. Seal bag and refrigerate for 30 minutes.
Place 1 inch of water in a large skillet; add sausage. Bring to a simmer; cover and simmer for 10 minutes. Cool sausage slightly; cut into 1-inch pieces.
Preheat grill to medium. On metal or soaked wooden skewers, alternately thread sausage, peppers, onion, pineapple and olives. Grill for 10 minutes or until browned, turning frequently and basting with remaining Italian dressing.
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