Pre-cook bacon: Halve bacon strips crosswise. Air fry at 390°F for 5 minutes. Remove — it will still be pliable.
Make glaze: Whisk ketchup, honey, Worcestershire, soy sauce, ginger, and Sriracha. Simmer in small saucepan 8–10 minutes until slightly thickened.
Wrap pineapple: Pat pineapple chunks very dry. Wrap one bacon piece around each chunk and secure with a soaked toothpick.
Glaze & air fry: Brush bites generously with glaze. Air fry at 390°F in a single layer for 3–5 minutes until bacon is crispy and caramelized. Work in batches.
Serve: Plate immediately. Serve hot or at room temperature.