Peel, devein, and wash the shrimp with lemon juice and cool water. Cut larger shrimp in half if necessary. Sourcing small raw shrimp in Ontario can be a bit challenging, though it's easy to get cooked small shrimp in the frozen section of the grocery store. Season the shrimp with 1 tbsp olive oil, 1/3 of the salt, 1/3 of the black pepper, Caribbean green seasoning, and anchar masala. Set aside to marinate.
Heat the remaining olive oil in a deep pot over low heat. Add garlic and cook for 2–3 minutes until fragrant.
Add the sliced butternut squash, raise the heat to medium, and stir to coat with the garlic oil.
After 1 minute, add the remaining salt and black pepper, onion, pimento pepper, habanero peppers (if using), and brown sugar. Stir well.
Cover the pot and bring to a boil. If needed, add 1/4 cup water, but the squash will usually release enough liquid. Reduce to medium-low and cook for 25 minutes with the lid on.
Meanwhile, in a non-stick pan over medium heat, cook the marinated shrimp for 90 seconds, stirring so they cook evenly. Remove from heat.
Uncover the squash, use the back of a spoon to crush larger pieces, and allow excess liquid to cook off.
Once dry (liquid from the squash is gone), add the shrimp to the pot, stir to combine, and adjust seasoning with salt if needed. Remove from heat.
Serve warm with roti, rice, or your favorite sides.
