How to Make It
Preheat oven to 425°F. Cut squash in half lengthwise; scoop out and discard seeds and membranes. Cut each half into 4 wedges. Toss together squash wedges, oil, 1 teaspoon salt, and pepper in a medium bowl. Arrange wedges, cut sides down, on a rimmed baking sheet lined with parchment paper.
Roast in preheated oven 20 minutes, turning once halfway through. Let cool 5 minutes. Arrange 1 whole sage leaf on rounded flesh side of each squash wedge; wrap 1 prosciutto strip around each squash wedge. Arrange squash wedges on pan, skin sides down. Roast in preheated oven until prosciutto is crisp and squash is tender, 10 to 15 minutes.
Meanwhile, melt butter in a 12-inch skillet over medium-high, stirring often with a wooden spoon, just until milk solids begin to sink to bottom of skillet and brown, 4 to 5 minutes. Add torn sage leaves; cook, stirring constantly, just until sage stops sizzling. Remove from heat, and let stand 1 minute. Carefully stir in sherry vinegar and remaining 1/4 teaspoon salt.
Transfer squash to a warm serving platter, and spoon browned butter sauce over squash. Drizzle with honey, if desired. Serve immediately.