Step 1: Preheat oven to 425 degrees F. Line a rimmed baking sheet with parchment paper.
Step 2: In a bowl sir together the squash, olive oil, 1/4 teaspoon salt, and 1/4 teaspoon pepper. Place in a single layer in prepared pan.
Step 3: Bake until tender (30 minutes). Set aside. Increase oven temperature to 450 degrees F.
Step 4: In a dutch oven, melt butter over medium heat. Add sage leaves and cook until crisp (1 minute). Using a slotted spoon, remove sage. Chop and set aside.
Step 5: Add flour to pan, whisking to combine. Cook, whisking constantly for one minute. Add milk, remaining 1 3/4 teaspoons salt, remaining 1/4 teaspoon pepper and nutmeg, whisking until smooth. Cook, stirring frequently, until thickened (5 minutes). Reduce heat to low. Add 1 cup Asiago and the monkery jack, stirring until melted. Add fried sage, fresh sage, cooked pasta and the roasted squash, stirring gently to combine. Remove from heat. Spoon mixture into 2-quart baking dish. Sprinkle with remaining 1/4 cup Asiago and panko.
Step 6: Bake until cheese melts and top is golden brown (8-10 minutes). Garnish with sage, if desired.
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