Preheat the oven to 400ºF/205ºC. Arrange two oven racks, one on the bottom and one in the middle.
Cook the lentils. Bring a medium Dutch oven or saucepan of water to a boil. Season with a few pinches of salt and add the lentils. Reduce heat and simmer for ~ 8 minutes. Taste a lentil—it should be cooked through but with a bite (you don’t want it to get soft). Drain well and transfer to a dish towel to dry out. Prep and roast the squash. While the lentils are cooking, slice the squash in half, vertically, then scoop out the seeds (no need to peel). See Note 2. Take a paring knife and make some crosshatch marks in the flesh, but don’t cut all the way through to the skin. Drizzle each half, flesh side up, with some olive oil and rub in. Season the flesh with salt and pepper. Line a rimmed sheet with parchment paper. Place squash flesh side down. Roast on bottom rack for 45 to 55 minutes, or until somewhat browned and fork tender. If making the Cashew Cream (see 2nd recipe card), start on that now.
Prep the lentils. Add the lentils to a second rimmed sheet pan and toss with 1 TBSP olive oil and sprinkle with a few pinches of salt and pepper. Spread out to distribute so there's minimal overlap. Set aside for now.
Roast the lentils: When the squash has 20 minutes left, add the pan of lentils to the middle oven rack. Roast for 15 minutes. If the lentils have not crisped up, shake the pan to toss and roast for 5 more minutes until crispy but not rock hard.
Meanwhile, cook the aromatics. Heat 2 TBSP olive oil in the saucepan used earlier over medium-high. Once hot, add the onions and season with a pinch of salt. Cook for about 7 minutes, or until softened and turning color. Add the garlic and cook for another 2 minutes, stirring frequently. Add the Spice Mix and stir for 30 seconds. Pour in 3 cups (720 mL) broth, scraping up any browned bits. Simmer for 5 minutes, then remove from the heat.
When the squash is done, peel off the skin with your hands. Transfer flesh to a 64 oz / 2L stand blender. See Note 3 if you don't have a blender or if yours is smaller. Pour in the onion-broth mixture, the coconut milk or Cashew Cream if using, 1 teaspoon kosher salt, and 1/2 tsp red wine vinegar (or lemon juice). Remove the center cap and cover with a dish towel to allow steam to vent. Blend until smooth, creamy, and warmed through. If too thick, add more broth or water. Taste, adding salt/pepper or vinegar to taste. Pour soup into bowls, top with crispy lentils, and chopped herbs, if using. Drizzle on a bit of good olive oil and sprinkle with a pinch of flaky salt; serve toast alongside the soup.