Heat the oven. Set your oven to 400°F (200°C). Line a baking sheet with parchment for easier cleanup.
Prep the squash. Using a sharp, sturdy knife, slice a thin piece off the bottom of the kabocha so it stands upright. Then cut the squash in half from top to bottom.
Scoop out the seeds and stringy bits. Rub the cut sides with 1 tablespoon of olive oil and season with salt and pepper.
Roast the squash. Place halves cut-side down on the baking sheet. Roast for 30–40 minutes, until the flesh is fork-tender and the edges are lightly caramelized.
The skin will soften and become edible.
Cook the filling base. While the squash roasts, heat the remaining tablespoon of olive oil in a large skillet over medium heat. Add the onion and cook 3–4 minutes until translucent. Stir in garlic and cook 30 seconds until fragrant.
Brown the protein. Add ground turkey (or your preferred protein) to the skillet.
Break it up with a spoon and cook until browned and cooked through. Season with cumin, smoked paprika, cinnamon, chili flakes, salt, and pepper.
Add vegetables and mix-ins. Stir in mushrooms and cook until they release moisture and brown slightly, about 3–4 minutes. Fold in chopped kale or spinach and cook until wilted.
Combine with grains and extras. Add the cooked grains, dried cranberries, and toasted nuts or seeds.
Toss until everything is evenly distributed. Taste and adjust seasoning. If using cheese, fold in half and reserve the rest for topping.
Stuff and return to oven. Flip the roasted squash halves cut-side up.
Spoon the filling into each cavity, mounding slightly. Top with remaining cheese if using. Return to the oven for 10–12 minutes, just to meld the flavors and lightly toast the top.
Finish and serve. Remove from the oven and let rest for 5 minutes.
Sprinkle with chopped parsley. Serve as halves for a hearty meal, or slice into wedges for smaller portions.