Mix the sugar, oil, salt, and ⅔ cup water in a large bowl until everything is dissolved. Using warm water helps.
In a separate bowl sprinkle the yeast over the 3 tbsp water. Sprinkle a dash of sugar on top. Set aside for at least 5 minutes until foamy looking.
In the large bowl, add 1 cup of flour and mix. All the clumps may not go away. It’s okay, you can go on to the next step!
Add about ½ cup of flour and the yeast mixture to the large bowl and mix.
Slowly continue adding flour. As your mixture becomes thicker, add the flour more and more slowly. Add flour until the dough only slightly sticks to your hands.
Knead the dough with your hands in the bowl at first for approximately 5 minutes. You’ll need to coat your hands with flour as needed, and continue reapplying the flour throughout so that the dough remains only slightly sticky to the touch. Then transfer the dough to a lightly floured surface and knead for 10 minutes more.
Alternatively, you can knead in a stand mixer using the dough hook for 10 minutes on a medium setting.
Transfer the dough back to the bowl (make sure it is lightly floured). Sprinkle flour on top of the dough and cover with a damp washcloth. Let is rise until doubled in size, for at least 30 minutes.
While the dough is rising, chop your apples and combine them with the cinnamon and sugar. Set aside for filling later.
After the dough has risen, preheat your over to 350 degrees F. Transfer your dough back to a lightly floured surface. Divide the dough into 4 equal balls of dough (if doing a round challah).
Roll the dough balls into strips between your hands.
Create a divet in the dough with your fingers down the center of each strip that you are going to fill.
Fill the divet with the apple cinnamon mixture, pushing the apple into the divet to really stuff the strand as you pinch the edges of the dough together to close the dough around the apple. Repeat for each strand.
See above for a link to a video on how to braid a 4 strand round challah.
Place the challah on a parchment paper lined tray. Cover the loaf with hand towels and let rise until doubled in size and puffy, at least 30 minutes.
Put your tray in the oven. Bake for 20 minutes.
While your challah is in the oven, create the wash for the top of the challah by mixing equal parts non-dairy milk with maple syrup. Mix the cinnamon sugar mixture in a separate bowl.
After the 20 minutes, remove the challah from the oven and wash with the mixture you created. Sprinkle the cinnamon sugar mixture over top of the challah as well.
Place the tray back in the oven for 20-30 more minutes, until golden brown and a fork placed in between the braids comes out clean. Another method you can try is tapping the bottom of the challah and seeing if it sounds hollow.
Once your challah is done, let it rest on the tray for a few minutes and then transfer to a wire rack to cool completely before eating.