Preheat your oven to 400°F (204°C) and line a baking sheet with parchment paper.
Halve the spaghetti squash and scoop out the seeds. Drizzle about 1 tablespoon of olive oil over the cut surfaces and sprinkle generously with salt and pepper. Place the halves cut-side down on the prepared baking sheet.
Roast the spaghetti squash in the preheated oven for 30 minutes, until tender.
In a bowl, combine the cherry tomatoes, minced garlic, minced shallot or onion, salt, pepper, and 3 tablespoons of olive oil. Toss until everything is nicely coated.
After the initial roasting time, turn the spaghetti squash halves over. Divide the cherry tomato mixture evenly between the squash halves. Cut the Boursin cheese in half and add one half to each squash half.
Return the stuffed squash to the oven and raise the temperature to 425°F. Bake for another 20-25 minutes, or until the cherry tomatoes begin to burst.
Remove the squash from the oven and let it cool slightly. Use a fork to shred the insides of the squash, mixing the strands with the filling. Stir in the fresh basil, adjusting seasoning as needed.
Transfer the mixture back into the squash halves and serve immediately.
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Notes
Store any leftovers in an airtight container in the refrigerator for up to 3-4 days.