Serves 12


  • 4 1/2 pounds kabocha or butternut squash, halved, seeded (peeled if using butternut), and cut into 3" chunks
  • 2 Tbsp. canola oil
  • 2 1/4 tsp. kosher salt, divided
  • 1/2 tsp. ground black pepper, divided
  • 3 Tbsp. unsalted butter, divided
  • 1 large shallot, finely chopped
  • 1 garlic clove, finely chopped
  • 1/4 cup sesame seeds
  • 1 tsp. ground cinnamon
  • 1 tsp. ground cumin
  • 1 star anise pod
  • 3/4 cup low-sodium chicken or vegetable broth
  • 1 1/2 Tbsp. light brown sugar
  • 2 ounces bittersweet chocolate (70% or more cacao), finely chopped (about 1/3 cup)
  • 3 Tbsp. shelled pumpkin seeds (pepitas), toasted


    Total time: 50 minutes

    Preheat oven to 400°. In a large bowl, toss squash with oil, 1 1/2 tsp. salt, and 1/4 tsp. pepper. Arrange in a single layer on two large rimmed baking sheets. Roast, flipping squash and rotating baking sheets halfway through, until deep golden brown and tender, about 35 minutes total.

    Meanwhile, in a small saucepan, melt 1 Tbsp. butter over medium-low heat. Add shallot and garlic and cook, stirring occasionally, until softened and translucent, about 5 minutes. Stir in sesame seeds, cinnamon, cumin, and star anise, and cook for 1 minute. Stir in broth and brown sugar, increase heat to medium, and cook until reduced by half, 5 to 7 minutes. Remove star anise and discard.

    Whisk in chocolate and remaining 2 Tbsp. butter until smooth. Remove from heat, stir in remaining 3/4 tsp. salt and remaining 1/4 tsp. pepper, and keep warm. Transfer squash to a platter, drizzle with sauce, sprinkle with pumpkin seeds, and serve.

    Make ahead: Prepare through removing the anise. Just before serving, rewarm sauce and continue with whisking in the chocolate and butter.

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