Add the yeast, the warm water, and a pinch of the sugar to the bowl of a stand mixer and let proof, 5-10 minutes. When bubbly, add the remaining sugar, the flour, and the oil to the bowl.

Using a paddle attachment, mix on medium speed until combined, about 1 minute. Turn the mixer to low and add the eggs one by one, waiting until each egg is well incorporated before adding the next.

Add the anise seeds and salt to the dough and mix for another minute to combine. The dough should be silky, sticky, and well-combined. Coat a large bowl with oil and gently fold the dough into the bowl. Oil the top of the dough and cover with plastic wrap. Let the dough rise overnight in the fridge; alternatively, let it rise for 2-2½ hours in a warm room.

Once the dough has doubled in volume, shape the challahs. Lightly flour your work surface. Tip the dough out onto the surface and separate the dough into 4-ounce balls. Roll each ball into a long strand, then combine 3 strands and braid together to make a 3-strand braided challah. Alternatively, braid into 6-strand challahs.

Repeat until all the dough has been used, placing shaped challahs on parchment paper-lined sheet pans. Let the challahs rise, covered, for another 2 hours, until doubled in size again. Preheat the oven to 350F.

Brush the challahs with the egg wash and sprinkle with the sesame seeds. Bake until deeply golden brown, 25-30 minutes.