Melt 4 tablespoons butter in a large pot over medium-low heat and add the onion, apples, potato and squash. Season with salt and pepper and cook until the onion is soft, about 8 minutes. Stir in the sage and flour. Add the cider and cook over high heat, stirring, until thickened. Add the broth and milk, cover and bring to a boil; reduce to a simmer and cook, stirring, until the potato is soft, 8 to 10 minutes.
Meanwhile, heat the remaining 1 tablespoon butter in a large skillet over medium-high heat. Add the prosciutto and cook until crisp, turning occasionally, about 2 minutes. Drain on paper towels.
Add the cheese to the soup and stir over medium-low heat until melted. Puree in a blender in batches until smooth; season with salt and pepper. Garnish with the prosciutto, more cheese and chives, if using. Serve with bread, if desired.
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Photograph by Antonis Achilleos
When blending hot liquid, first let it cool for five minutes or so, then transfer it to a blender, filling only halfway. Put the lid on, leaving one corner open. Cover the lid with a kitchen towel to catch splatters, and pulse until smooth.
Courtesy of Food Network Magazine
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