Set the oven to bake at 425F.
Slice the whole squash lengthwise and scoop out the seeds.
Lightly spray the squash with canola or coconut oil.
Turn the squash cut-side down onto a lined baking sheet and bake for 45 -60 minutes until a knife easily pierces the squash.
Although the roasted squash may brown on the inside, this adds flavor to the dish.
You can bake your squash ahead of time and set aside until you’re ready to prepare the recipe.
Reduce the oven temperature to 375F.
While the squash is cooling (or once you’re ready to prepare the sauce), place the tomatoes in a 3-qt baking dish (any shape). With a potato masher or large fork, crush the tomatoes.
Add the remaining ingredients (except the cheese) to the tomato mixture: oil, garlic, sugar, Italian seasoning, kosher salt, red pepper flakes, and black pepper. Stir to combine.
Bake the sauce until it's bubbly, about 35 minutes.
Remove from the oven, stir the sauce, and further mash the tomatoes if needed.
Scoop the strands of squash out of the skin (do not add the skin to the sauce). Combine with the tomato sauce.
Sprinkle the shredded cheese on top. Add a pinch of the Italian seasoning, salt, and freshly cracked pepper over the cheese.
Return the baking dish to the oven and bake for 12 minutes until the cheese is bubbling on top.
Salt and pepper as needed
Note: If only large squash are available, only use half because the squash to tomato ratio is important.
Another way to bake the squash is to stuff the squash and tomato mixture into the empty shells. Top with cheese and bake for 12 minutes.