In a large bowl, mix the pumpkin puree, cinnamon, brown sugar, yeast, salt, olive oil, warm water and egg yolks.
Gradually mix in the flour until the dough reaches a crumbly consistency.
Place the dough on a flat surface and knead for 5 minutes, adding more flour if the dough feels sticky.
Transfer dough to a greased bowl, cover with a towel, and let it rise for 1 hour (or until doubled in size).
Meanwhile, make the filling by mixing together the pumpkin puree, cinnamon and brown sugar in a medium sized bowl.
Preheat the June Oven to 350℉ on the June Oven App.
Cut off a piece of dough about the size of a tennis ball and roll it out into a rectangle.
Spread the filling in the middle or the dough then roll it up into a long string.
Tie the strand of dough into a knot and pinch the two ends together.
Egg wash the challah and sprinkle with some chopped nuts. The allow the dough to rise for 20 minutes.
Bake for 15-20 minutes in the June oven until the top is perfectly golden. Keep an eye on the baking progress in the 'Live Video' tab in the June App!