Preheat your oven to 400 F. Cut the squash in half, remove and discard the seeds and core, and place it on a lined baking tray. Drizzle with 1 tablespoon olive oil, 1/4 tablespoon salt, and 1/4 tablespoon black pepper. Roast until tender and lightly caramelized around the edges.
Heat the remaining olive oil in your soup pot over medium-high heat. Add the beef pieces and cook until slightly browned, allowing them to develop color and begin releasing their flavor.
Add the celery, onion, ginger, thyme, Caribbean Green Seasoning, and garlic. Continue cooking for 3 to 4 minutes. The sizzling and aroma of the herbs should be intoxicating as they bloom in the hot oil. Add the remaining salt, 3/4 of the remaining black pepper, lentils, carrot, and beef stock.
Add the stewed tomatoes, followed by the whole scotch bonnet pepper and coconut milk. Bring to a boil, then reduce to a simmer and cook. 1/2 cup of pure coconut cream will also work.
After 35 to 40 minutes, remove the roasted squash from the oven. When cool enough to handle safely, scoop out the flesh and add it directly to the soup pot.
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Continue cooking for 1 hour and 15 minutes from the time the soup reached a rolling boil, adding 4 cups of water to start and more as necessary to maintain the desired consistency.
Peel and rinse the potatoes and sweet potato. Cut into large pieces and add to the soup pot. Cook for another 30 minutes. The goal is melt-in-your-mouth pieces of beef and an almost velvety texture from the coconut milk, roasted squash, and lentils, which will begin breaking down at this stage.
NOTE! In the Caribbean it's normal to add dasheen (taro), eddoes, green cooking bananas, flour dumplings, and yam to this sort of soup.
Depending on the age and cut of the beef, it may take longer to become fork-tender. Add more water and continue cooking if necessary. Remove the scotch bonnet pepper for controlled heat, or break it to release more spice. You may also remove the ginger and sprigs of thyme.
Finish with the chopped parsley and scallions. Add the remaining black pepper, taste, and adjust the salt to your liking. Keep in mind that beef stock is not traditionally used in many Caribbean soups, but it captures the essence of the beef beautifully. Be mindful of its sodium content.