Fig Butter & Nutella Challah

Directions

1. To make dough with a stand mixer: Whisk the yeast and 1 teaspoon honey into warm water, and let it stand for a few minutes, until foamy. In a large mixer bowl, combine the yeast mixture with remaining honey, 1/3 cup olive oil, and eggs. Add the salt and flour, and mix until dough begins to hold together. Switch to a dough hook, and run at low speed for 5 to 8 minutes. Transfer the dough to an olive-oil coated bowl (or rest the dough briefly on the counter and oil your mixer bowl to use for rising, so that you’ll use fewer dishes), cover with plastic wrap, and set aside for 1 hour, or until almost doubled in size.
2. Meanwhile, make fig paste: In a saucepan combine sugar with ¼ cup water and stir over medium heat until sugar dissolves. Add the figs, red wine, port and cinnamon stick. Bring to a boil and then reduce heat to a simmer and cook until figs are very soft and liquid has reduced by about half (takes about 25-30 minutes). Take figs off the heat and let cool. Take out the cinnamon stick. Once cool, place figs and their liquid in a food processor and process until very smooth. Add the soft butter and process again. Set aside.
3. Insert filling: After your dough has risen, turn it out onto a floured counter and divide it in half. Roll the first half of the dough into a wide and totally imperfect rectangle (really, the shape doesn’t matter). Spread ½ cup Nutella evenly over the dough, stopping short of the edge. Repeat with 1/2 cup fig butter and spread evenly over the dough. Roll the dough into a long, tight log, trapping the filling within. Then gently stretch the log as wide as feels comfortable (I take mine to my max counter width, a pathetic three feet), and divide it in half. Repeat with remaining dough,1/2 cup Nutella and ½ cup fig butter.
4. Weave your challah: Arrange two ropes in each direction, perpendicular to each other, like a tight tic-tac-toe board. Weave them so that one side is over, and the other is under, where they meet. So, now you’ve got an eight-legged woven-headed octopus. Take the four legs that come from underneath the center and move the leg to their right — i.e., jumping it. Take the legs that were on the right and, again, jump each over the leg before, this time to the left. If you have extra length in your ropes, you can repeat these left-right jumps until you run out of rope. Tuck the corners or odd bumps under the dough with the sides of your hands to form a round.
5. Transfer the dough to a parchment-cover heavy baking sheet, or, if you’ll be using a bread stone, a baker’s peel. Beat egg until smooth, and brush over challah. Let challah rise for another hour, but 45 minutes into this rise, preheat your oven to 375°F.
6. Bake your loaf: Before baking, brush loaf one more time with egg wash and sprinkle with sea salt. Bake in middle of oven for 30 to 40 minutes. It should be beautifully bronzed; if yours starts getting too dark too quickly, cover it with foil for the remainder of the baking time. The very best way to check for doneness is with an instant-read thermometer — the center of the loaf should be 195 degrees. Let cool at least 20 minutes before cutting into it.