01 -
Preheat the oven to 400°F (205°C). Cut the butternut squashes in half lengthwise, scoop out the seeds, and brush cut sides with olive oil. Season generously with salt and pepper. Place halves cut-side down on a parchment-lined baking sheet.
02 -
Roast the squash in the oven for 30 to 40 minutes, or until the flesh is very tender when pierced with a fork but still holds its shape.
03 -
While squash roasts, heat a large skillet over medium heat. Add a drizzle of olive oil, then add chopped onion. Sauté until soft and translucent, about 5 minutes.
04 -
Add loose Italian sausage to the skillet, breaking it into small crumbles. Cook until fully browned, about 7–9 minutes. Drain off excess fat if needed.
05 -
Add minced garlic and Italian seasoning to the pan. Sauté for 30 seconds until fragrant.
06 -
Toss in fresh spinach, stirring until wilted, about 1–2 minutes. Remove pan from heat once spinach is combined.
07 -
Stir in dried cranberries and toasted pecans. Mix thoroughly with the residual heat to soften cranberries slightly while maintaining nut crunch.
08 -
When the squash is cool enough to handle, turn cut sides up. Gently scoop out some flesh, leaving about a 1-inch border to form a shell. Roughly chop scooped squash and fold into the sausage mixture.
09 -
Fill each squash shell generously with the sausage mixture. Mound filling slightly if desired. Top with grated Parmesan or Gruyere cheese if using.
10 -
Return stuffed squashes to the oven and bake for 5 minutes at 400°F (205°C), just until cheese is melted and filling is heated through.
11 -
Finish with fresh thyme or sage if desired. Serve warm, slicing squash halves into portions as needed.