In a medium bowl, pour ½ cup of warm water. Sprinkle yeast and granulated sugar and then stir to dissolve. Allow it to stand until foamy, about 10 minutes. Set aside ¼ cup of flour.
In the bowl of an electric mixer fitted with the paddle attachment, combine the 3/4 cup warm water, milk, butter, granulated sugar, ground cinnamon, salt, egg and 2 cups of flour. Beat on medium speed until nice and creamy, about 1 minute or so. Add the yeast mixture and 1 cup of flour and mix on medium speed for about 1 minute. Add the raisins, and then add the remaining flour, 1 cup or so at a time, until the dough pulls away from the sides of the bowl. The dough should look shaggy, resembling cookie dough a bit.
Turn the dough onto a very lightly floured surface. Pour reserved ¼ cup of flour on the counter next to your dough. Begin to knead the dough, periodically dusting your hands with the flour. This prevents you from adding excess flour to the dough and toughening your product. Continue kneading this way until the dough is slightly tacky but not sticky to the touch, about 10 minutes or so. Gather the dough into a rough circle and set aside.
Using neutral oil, lightly oil a large bowl and transfer your dough to the bowl. Turn it a couple of times to lightly coat. Cover loosely with plastic wrap and allow it to rise at room temperature until doubled in bulk, 1 to 1 1⁄2 hours.
Preheat the oven to 350° Fahrenheit. Lightly grease two 9-by-5-inch loaf pans and set aside.
Once the dough has fully risen, turn it onto a lightly floured surface. Divide the dough in half and press each half into an 8-by-14 inch rectangle. The thickness doesn’t really matter as long as it’s uniform. Cover one rectangle with plastic wrap. Lightly spoon and spread one rectangle with half of the filling, leaving a 1-inch border on all sides. Beginning at a narrow end, tightly roll up each rectangle into a very compact log. Pinch the long seam and tuck in the ends to seal the filling. Pinching the seams and tucking the ends is crucial as the spices in the filling can become very bitter should the filling seep out. Place the bread log, seam side down, in a prepared pan. Cover loosely with plastic wrap. Repeat with the second rectangle of bread dough and allow them both to rise at room temperature until the dough is about 1 inch above the rim of each pan, 1 to 1 1⁄2 hours.
Bake until the loaves are golden brown, pull away from the sides of the pan, and the internal temperature reaches 190° Fahrenheit, 35 to 40 minutes. Turn the loaves out onto wire racks and allow them to cool completely before slicing.
Makes two 9-by-5-inch loaves.
Adapted from: Annie's Eats