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In a standing mixer bowl mix together flour and yeast.
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Add in sugar, milk, butter, and eggs with a dough hook mix on medium speed for 4 minutes. Add in salt and keep mixing for 7 more minutes, roll the dough into a ball cover with a plastic wrap and let rise for at least 45 minutes or until dough doubles in size.
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While dough rises make the filling. In a small bowl mix cocoa powder, sugar, and oil, and set aside.
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Divide dough into 4 equal parts. Working each part individually roll out the dough to about 1/8 inch thick rectangle.
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Spread 1/4 of the filling on 1/2 of the rectangle and fold the other half over like a blanket. With a rolling pin, roll the filled dough as thin as you can.
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Cut the filled dough into triangles. Roll each triangle from wide to narrow, you will end up with point on outside of rugelach. Place on ungreased baking sheets 2 inches apart, cover with a clean kitchen towel and let rise for 30 minutes.
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Preheat the oven to 350°F/180°C. Brush rugelach with egg wash and bake for 20-25 min or until lightly golden.
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While rugelach are in the oven make the topping. Combine sugar and water in a small pot place over high heat and bring to a boil. Once you remove rugelach from oven brush them with the sugar and water and let cool.