Preheat your oven to 400°F.
In a large mixing bowl, toss the squash with 1 tbsp olive oil, 1 tsp salt, 1 tsp pepper, cinnamon, and cumin until evenly coated. Spread the squash on a baking sheet in a single layer. Roast in the oven for 30 minutes, or until tender and slightly caramelized, stirring halfway through.
While the squash is roasting, heat a large pot over medium heat. Add remaining olive oil and sauté the onion until translucent, about 5 minutes. Add the garlic and cook for another minute until fragrant. Stir in the pearl couscous and toast for 3 minutes, stirring occasionally.
Once the butternut squash is done roasting, add it to the pot with the couscous. Prepare couscous according to package directions replacing the water with the broth.
When couscous is finished, fluff the couscous with a fork and stir in the cranberries. Garnish with spinach and sprinkle with feta.