Preheat your oven to 400°F. Toss diced squash with olive oil, curry powder, salt, and pepper. Roast for 20–25 minutes until tender and slightly caramelized.
Mash the roasted squash lightly with a fork, stir in honey and chopped green onions. Season with salt and pepper. This filling is naturally sweet and slightly spicy.
Place a spoonful of filling in the center of each wonton wrapper. Fold and pinch to seal into round dumplings. Brush bottoms with water and sprinkle sesame seeds for crunch.
In a saucepan, caramelize shallots in a little oil until golden. Add garlic and ginger, cook briefly, then pour in vegetable broth, soy sauce, and rice vinegar. Simmer for 5–7 minutes to infuse flavors.
Heat a skillet with a bit of oil. Add dumplings, pan-fry for 2–3 minutes, then pour in a splash of water and cover to steam until fully cooked, about 5 minutes.
Ladle hot broth into bowls, add dumplings, and finish with a drizzle of chili crisp and extra green onions. Enjoy immediately for best flavor.