Honey-Vanilla Challah

Directions

1. 1
   In a large bowl, use a whisk to combine the yeast, sugar, salt and 1 cup of the flour. Add warm milk, 2 eggs, 4 tbsp olive oil, honey, and vanilla. Vigorously mix the ingredients until smooth, scraping the sides of the bowl halfway through, about 3 minutes. Add remaining flour, 1/2 cup at a time, switching to a wooden spoon when the dough becomes too thick for the whisk. Continue mixing the dough until too stiff to stir.
2. 2
   Turn the dough out onto a lightly floured surface and knead until soft and springy, about 4 minutes. If the dough is sticky, dust with flour 1 tablespoon at a time - just enough to prevent it from sticking to the surface. The dough is done when it's smooth and small air bubbles show under the skin. If you press your thumb into it the impression should bounce back. This is a slightly firm dough, which is exactly what you want for easy braiding later on.
3. 3
   Place the dough in a deep container greased with 1 tsp of olive oil. Turn the dough once to coat the top and cover with plastic wrap. Allow it to rise at room temperature until doubled in bulk, about 1 1/2 to 2 hours.
4. 4
   Line a baking sheet with parchment paper or lightly grease it with non-stick spray. Gently deflate the dough by pressing your fingers into it, then turn it out onto a lightly floured surface.
5. 5
   Divide into 3 equal portions, and roll each portion out into a smooth, thick strip about 20 inches long, with the ends slightly thinner than the middle. Lay these ropes side-by-side, not quite touching.
6. 6
   Beginning in the middle and working towards you, braid the lower half of the three ropes. To braid, alternately move the outside ropes over the one in the center - left over, right over, left over -until you come to the end. Now go to the other side of your working space and braid the other half, this time moving the outside ropes under the center one. Braid tightly - you don't want any gaps. When you finish braiding each side crimp the tapered ends together, then tuck them under.
7. 7
   Preheat oven to 350 °F and place the braided dough on a baking sheet. Cover loosely with plastic wrap and let rise until almost doubled in bulk, 30 to 40 minutes.
8. 8
   Just before the rising time has finished whisk together 1 egg and 1 teaspoon of olive oil, this is going to be the glaze for your bread. Gently brush the dough with a thick layer of it. Place the dough in the oven and bake for 30 to 35 minutes, or until the bread is a deep golden brown and sounds hollow when you thump it on the bottom. Transfer to a baking rack to cool. Allow to cool before slicing.