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1
Combine cinnamon and 3 tablespoons sugar; set aside.
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2
Combine 5 cups flour and yeast in a mixing bowl. Combine water and milk; gradually add to flour mixture, beating at medium speed of a heavy-duty stand mixer until well blended.
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3
Combine squash, molasses, oil, and salt; add to flour mixture, beating well. Add enough of remaining flour, 1 tablespoon at a time, to form a soft dough.
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4
Turn dough out onto a lightly floured surface. Knead until smooth and elastic (about 10 minutes), adding enough of remaining flour, 1 tablespoon at a time, to prevent dough from sticking to hands.
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5
Place dough in a large bowl coated with cooking spray, turning to coat top. Cover and let rise in a warm place (85u00b0), free from drafts, 25 minutes or until doubled in bulk. Punch dough down; turn dough out onto a lightly floured surface, and knead 5 times. Divide dough in half. Working with 1 portion at a time, (cover remaining dough to keep it from drying out), roll each portion into a 16- x 7-inch rectangle. Brush each with 1 tablespoon melted butter; sprinkle with half of reserved cinnamon-sugar mixture and half of raisins. Roll up each rectangle tightly, starting with short side. Press firmly to eliminate air pockets; pinch seam and ends to seal. Place each roll of dough, seam side down, in a 9- x 5-inch loaf pan coated with cooking spray. Cover and let rise 20 minutes or until doubled in bulk.
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6
Preheat oven to 350u00b0.
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7
Bake at 350u00b0 for 30 minutes or until loaves sound hollow when tapped. Remove from pans immediately, and let cool on wire racks.
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8
Combine powdered sugar, milk, and vanilla, stirring well. Drizzle over loaves.
