Carefully cut the spaghetti squash in half lengthwise and scoop out the seeds.
Brush the inside of each half with 2 tablespoons of olive oil, then season with salt and pepper.
Place the squash halves cut-side down on a baking sheet lined with parchment paper.
Roast in the preheated oven for 30-40 minutes until the flesh is tender and can be shredded with a fork.
While the squash is roasting, heat the remaining 2 tablespoons of olive oil in a large skillet over medium heat.
Add the minced garlic and sauté for about 1 minute until fragrant but not browned.
Stir in the chopped spinach and cherry tomatoes, cooking for 3-4 minutes until the spinach is wilted and the tomatoes are slightly soft.
Remove the skillet from heat and mix in the grated Parmesan cheese and Italian seasoning. Adjust seasoning with salt and pepper to taste.
Once the spaghetti squash is cooked, use a fork to scrape the flesh into spaghetti-like strands, then gently mix with the garlic, spinach, and tomato mixture.
Spoon the mixture back into the squash halves, generously filling each one.
Return the stuffed squash boats to the oven and bake for an additional 10 minutes until heated through and the tops are slightly golden.
Notes
Serve hot, garnished with fresh basil leaves and an extra sprinkle of Parmesan cheese for a lovely finish.