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Slice onion, carrots, leek, and celery and set aside.
Heat 2 tbsp. olive oil in a medium sized saucepan on medium heat. Add 1 crushed garlic and saute for 1 minute until fragrant.
Devein prawns. Remove shells, tails, and heads and place them in saucepan with garlic. Cut and set prawn meat aside.
Saute shells, tails, and heads for 4-5 minutes on medium heat, frequently crushing them gently with a wooden spoon to release juices.
Add sliced vegetables and bay leaves and saute for 5 minutes on low heat. Add some water if mixture starts to dry out. Add white wine and stir until alcohol evaporates.
Add canned chopped tomatoes and ¼ cup water (60mL) and simmer for 15 minutes. Add some water if mixture starts to dry out.
Boil pasta in salted water 1 minute less than package instructions until al dente. Reserve ½ cup of pasta water.
Whilst bisque is simmering, place 2 tbsp. olive oil in a large skillet on medium heat. Add 1 crushed garlic and saute until fragrant (about 1 minute). Add Italian seasoning, oregano, and chilli pepper (if using) and cherry tomatoes and saute (sliced side facing down) for 3-4 minutes until soft (add 3-4 tbsp. of water if they start to dry out).
Add prawn meat and cook for 1-2 minutes, stirring frequently using a wooden spoon.
Strain liquid out of prawn bisque and transfer to skillet with tomatoes. Add ¼ to ½ cup of pasta water and season with salt and pepper to taste. Simmer for 2-4 minutes.
Toss cooked pasta into skillet, coat well with sauce and serve.