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1
Make the dough: In a large electric mixer bowl, dissolve yeast in 1/4 cup warm milk.
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2
Add the remaining warm milk, the sugar, the salt, the butter and the eggs.
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3
Add 5 cups flour and mix with paddle attachment until smooth, about 2 minutes.
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4
Switch to hook attachment and knead on low speed, adding more flour if necessary until dough is stiff and slightly tacky, about 10 minutes.
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5
Grease a large bowl with butter and turn dough out into the bowl.
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6
Flip dough over so greased side is up, cover with plastic wrap or a kitchen towel and set in a warm, draft-free spot until doubled in size, about 11/2 to 2 hours.
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7
Generously butter two 9-x-5 loaf pans.
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8
Meanwhile, make the filling: In a small pot, bring sherry to a low boil and simmer until reduced by half, about 8 to 10 minutes.
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9
Add raisins, cover and let sit until needed for filling.
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10
When dough has doubled in size, turn dough out onto floured surface and knead for 3 minutes.
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11
Return to greased bowl, cover and let rise again for 30 minutes.
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12
Press down dough with your hand to expel the air.
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13
Divide dough in half and roll one half into a 16-x-8-inch rectangle.
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14
Brush with some of the melted butter.
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15
Drain raisins and mix with sugar and cinnamon; scatter half of the mixture over the dough and, starting with the shorter side, roll up tightly into an 8-inch log, tucking the ends under.
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16
Place roll seam-side down in a loaf pan and brush top with melted butter; dust with cinnamon sugar if desired.
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17
Repeat with second dough half.
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18
Cover and let rise until dough is just above the tops of pans, 45 minutes to 1 hour.
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19
Meanwhile, heat oven to 400 degrees.
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20
Bake bread for 10 minutes, then reduce heat to 350 degrees and bake for an additional 20 to 30 minutes, or until loaves sound hollow when tapped, the tops are brown and the internal temperatures are 200 degrees.
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21
Remove loaves from pans and let cool on wire racks.
