Preheat the oven to 400°F (200°C). Toss the squash with olive oil, salt, and pepper on a sheet pan. Roast 25-30 minutes, stirring once, until tender and caramelized at the edges.
Meanwhile, bring the vegetable broth to a low simmer in a saucepan and keep it warm on the back burner.
Melt 2 tablespoons butter in a wide, heavy pot over medium heat. Add the onion and cook 4-5 minutes until soft. Add the rice and stir 1-2 minutes until the edges look translucent.
Pour in the white wine and stir until mostly absorbed, about 1-2 minutes.
Add the warm broth one ladleful at a time, stirring frequently and waiting for each addition to be mostly absorbed before adding the next. Continue for 20-25 minutes until the rice is creamy and just tender.
Remove from heat and stir in the remaining 2 tablespoons butter, parmesan, and chopped sage. Fold in two-thirds of the roasted squash, mashing it slightly into the risotto; reserve the rest for topping. Season with salt and pepper.
Divide the risotto among bowls, top with the reserved roasted squash and a few sage leaves, and finish with extra parmesan.
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