Preheat oven to 425°F (220°C).Cut squash in half lengthwise, remove seeds, lightly drizzle with olive oil and season with salt and garlic powder. Roast for 30–40 minutes, depending on size. It should be tender but slightly firm (al dente). Overcooking will make it mushy. On a separate tray, add bell peppers (halved), unpeeled garlic cloves under neath the bell peppers and sliced purple onion. Lightly drizzle with olive oil. Roast for 25–30 minutes at the same time as the spaghetti squash, until peppers are charred and soft. Once done, peel the skin off the peppers while they’re still warm.
In a large pan over medium-high heat, add 1 tsp olive oil. Add the ground beef and cook until browned, breaking it up as it cooks. Once water has evaporated and meat has brown a bit, add garlic, onion, diced red pepper, sofrito and tomato paste. Add salt, black pepper, garlic powder, onion powder, paprika, and oregano. Continue cooking and add small splashes of water to deepen the color and prevent burning. Once browned and flavorful, add enough water to just cover the beef then add your bay leaf and thyme sprig. Let it simmer until the water evaporates. Repeat one more time once water has evaporated, taste for seasoning and adjust if needed and then add water one more time but only enough water to cover halfway. Finish with a splash of white vinegar, taste for seasoning and let the beef dry out as much or as little as you'd like. Remove meat from pan and set aside.
Blend the roasted peppers, garlic, and onion until smooth. Pour the sauce into the same pan used for the meat.Season with salt, pepper, garlic powder, and Italian seasoning (and chili flakes or scotch bonnet if you like spice). Not too much salt if you're using feta cheese FYI. Add 1 oz of feta for extra creaminess (optional). Use a fork to shred the spaghetti squash into strands (about 300g per serving). Toss the squash into the sauce with tongs until well coated. Add 4 oz of picadillo per serving and mix until everything is combined and heated through.
Top with fresh cilantro, extra feta and serve right back in the squash shell for a perfect meal prep dinner. Store all ingredients separately and then easily combine over stove top in 2-3 minutes for dinner!
