Heat oil in a large heavy wide pot over medium heat. Add shallots, Panang Curry Paste , and ginger; stir until shallots begin to soften, 23 minutes. Add 1/3 cup coconut milk; stir until browned, about 4 minutes.
Add remaining 2 cups coconut milk, 1 1/2 cups vegetable stock, lime leaves, and chiles; stir to blend, scraping up browned bits. Add kabocha squash to pot, set on sides so all pieces fit in a single layer. Bring to a boil, reduce heat to medium-low, cover, and simmer until squash is almost tender, 1520 minutes. Remove squash from pot; stir in cauliflower, carrots, and peppers. Return squash to pot, placing on top of vegetables; cook until all vegetables are tender, 1015 minutes. Transfer squash to a plate.
Stir tamarind concentrate, half of basil, fish sauce, and lime juice into pot; add tofu. Cover and simmer until heated through, about 2 minutes, adding more stock if too thick. Season to taste with salt.
Divide curry among bowls; top each with 1 wedge of squash; sprinkle remaining basil and peanuts over. Serve curry with steamed jasmine rice.