01 -
Preheat oven to 400°F. Using a sharp knife, slice the butternut squash lengthwise and remove seeds. Drizzle with olive oil and season cut sides generously with salt and pepper.
02 -
Place squash halves cut-side down on a parchment-lined baking sheet. Roast for 35-40 minutes until completely tender when pierced with a fork yet still holding shape.
03 -
While the squash bakes, heat a large skillet over medium heat. Add diced onion and cook until translucent and just starting to brown, about 5 minutes. Add the Italian sausage, breaking it into crumbles, and cook until browned and cooked through.
04 -
Stir in the garlic and Italian seasoning. Sauté for 30 seconds until fragrant. Drain excess fat if necessary.
05 -
Add chopped spinach and cook, stirring frequently, until wilted and integrated, about 2 minutes.
06 -
Remove pan from heat. Mix in dried cranberries and toasted pecans, allowing residual warmth to soften cranberries slightly.
07 -
When squash halves are cool enough to handle, turn cut-side up and gently scoop out the center, leaving a 1-inch edge. Chop scooped flesh roughly and fold into the sausage mixture.
08 -
Divide the filling evenly among the hollowed squash halves, mounding slightly. Sprinkle with grated cheese if using.
09 -
Return filled squash to oven and bake at 400°F for 5 minutes, or until cheese melts and filling is heated through.
10 -
Top each squash half with chopped fresh herbs before serving. Serve hot.