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Tender roasted butternut squash halves are caramelized in the oven, then drizzled with rich garlic herb cowboy butter made with Dijon, lemon, fresh herbs, and a little crushed red pepper.
Preheat the oven to 425°F. Line a large rimmed baking sheet with parchment paper.
Carefully cut each butternut squash in half lengthwise. Scoop out and discard the seeds.
Place the squash halves cut-side up on the prepared baking sheet. Drizzle with olive oil, then season with salt, black pepper, smoked paprika, and garlic powder.
Roast for 35 to 40 minutes, until the squash is fork-tender and deeply golden around the edges.
While the squash roasts, melt the butter in a small saucepan over medium-low heat. Add the garlic and cook for 30 seconds, just until fragrant.
Remove the pan from the heat. Stir in the Dijon mustard, lemon juice, smoked paprika, red pepper flakes, Italian seasoning, parsley, and chives.
Transfer the roasted squash halves to a serving platter. Drizzle the warm cowboy butter generously over the cut sides.
Sprinkle with Parmesan, if using, plus extra fresh herbs and flaky salt. Serve warm.