To make the challah, add the yeast, 1 cup of warm water, yeast and sugar. Mix lightly with a fork to get all the yeast in the water and set aside for about 10 minutes. It should begin to foam up and you should see little bubbles.
Next, add eggs, oil and honey and whisk together.
Gradually add the flour and salt, about ½ cup at a time and mix until everything is incorporated.
Turn the dough onto a very well floured surface and knead for about 8-10 minutes. You can use your finger to see if it’s ready. Press your finger in and if the dough bounces back quickly, it’s ready.
Place the dough in a lightly oiled bowl and turn it around so the entire dough is covered with a thin layer of oil.
Cover with a clean towel or plastic wrap and place bowl in a warm spot to rise for 1- 1 ½ hours until doubled in size
While the dough rises, make the filling. In a small pot add the dried fruit, water, cinnamon stick, rosemary sprig and vanilla and cook for 10 minutes, until the dried fruit softens and water has evaporated.
Remove the cinnamon stick and rosemary and let cool for a few minutes, then add mixture to a food processor and blend until smooth and it's a thick paste.
Preheat oven to 350 degrees Fahrenheit
Once dough has doubled in size, punch the dough down and divide dough into 2 balls, this will be your challah.
Divide dough into 3 pieces (or more if you’re making another braid), these will be your braid strands. Take 1 of the strands and roll making a long snake, about 12-15 inches long and flatten to make room for the filling.
Next use a tablespoon to fill the strand with the dried fruit mixture. You can also press the mixture gently in the dough, but don’t overfill.
Bring the strand together, pinching with your fingers and making sure no filling peeks out (but it’s ok it some does). Once strands are sealed, gently roll the strands and begin braiding.
Line 3 strands together and pinch at 1 end. Braid a 3-strand bread and pinch the bottom ends together. Then turn braid onto itself to form a circle.
Place challah on baking sheet and let it rise for another 20-30 minutes. Then whisk egg yolks together and brush challahs with egg wash.
Bake challah at 350 degrees Fahrenheit for about 30 minutes or until the challah is a light golden brown color.