Mix ½ cup warm water, 1 Tbsp. sugar, and yeast in a small bowl. Let sit about 10 minutes at room temperature, until it becomes foamy.
Beat 5 eggs in a large bowl, then ad oil, ¾ cup sugar, and salt. Beat until lighter in color and thickened, about 4 minutes. Continue beating and add 2/3 cup warm water plus the yeast mixture. Beat till well blended.
Add flour a cup at a time, enveloping it into the wet ingredients each time until it becomes homogenous and forms a smooth dough. Once it’s fully incorporated (about 5 minutes), transfer to a lightly floured surface and knead dough 2 minutes, adding a bit of flour if it’s sticky.
Oil a large bowl and add the dough, turning it to coat with oil. Cover it with plastic wrap and a kitchen towel. Leave to rise in a warm, draft-free area of your kitchen for about an hour.
When it’s doubled in size, punch down, cover again with plastic and bowl and leave to rise another 30 minutes.
Butter or oil 2 large baking sheets. Preheat oven to 400°.
Transfer dough to a lightly floured surface and divide into 2 equal portions.
Now turn on this video and get to braiding!
Whisk yolk and Tbsp. of water; brush dough with egg mixture and sprinkle both generously with fennel seeds (as many as you’d like).
Bake 10 minutes, then reduce oven to 350°. Bake till bread is golden brown and sounds hollow when tapped on bottom, 25-30 minutes. Let loaves cool on a rack if you have the discipline. Otherwise just break off a hunk of bread and smear it with butter and put it in your mouth. I mean, let’s be real.
Spiced Apple Butter
Place all ingredients in a sauce pot and bring to a boil. Reduce to a simmer. Stir occasionally, and let simmer on low heat for 50 minutes to an hour, or until the liquid is largely reduced and the sauce has thickened and turned a rich chestnut color. Don’t increase the maple syrup until the end of cooking, because the flavor will evolve and deepen over its course of cooking.
When finished, let cool and serve with challah and butter.