Place the warm water in a large bowl or stand mixer. Add a pinch of the sugar to the bowl and sprinkle with the yeast. Set aside in a warm place for 5 to 10 minutes, until the mixture is foamy. (If your yeast doesn't proof properly, discard the mixture and start again with fresh yeast).
With a hand whisk or the mixer's whisk attachment, mix in the sugar, oil, 2 cups of flour, and salt. Switch to a sturdy wooden spoon or the mixer's dough hook, and add the remaining flour 1 cup at a time, mixing well after each addition until a shaggy dough forms and begins to pull into a ball. (You might or might not need the last 1/2 cup of flour. If the dough is very wet or sticky, add it. If not, use some of it to dust your work surface.)
Turn the dough out onto a lightly floured work surface. With clean, floured hands, knead the dough until it is smooth and elastic, about 5 to 10 minutes. Allow the dough to rest for a few minutes while you clean and dry the large mixing bowl. Grease the inside of the bowl with a bit of oil. Place the challah dough in the bowl and turn to coat with the oil. Cover the bowl with a damp tea towel or plastic wrap and set aside in a warm place until the dough has risen to at least double its bulk, about 1 hour and 45 minutes.
Punch the dough down. Lightly grease one or two baking sheets or line them with parchment paper. Shape or braid the dough as desired. (The recipe will make 1 large challah, 2 medium challahs, 1 medium challah plus 6 challah rolls, or 12 challah rolls.)
Place the shaped challah and/or rolls on the baking sheet(s) and cover with clean, dry tea towels. Allow to rise until doubled, about 45 minutes to 1 hour.
Heat the oven to 350° F. While the oven is heating, make the maple wash by whisking together the maple syrup, vanilla extract, and non-dairy milk. Brush over the challah with a pastry brush. Bake the challah until the crust is a deep golden brown and the loaf sounds hollow when tapped, about 30 to 35 minutes for a large challah, 20 to 25 minutes for a medium challah, and 15 to 20 minutes for rolls. Cool on a wire rack.
Serve and enjoy!

1 1/4 cup lukewarm water
2 1/2 teaspoon active dry yeast
8 tablespoon sugar
1/4 cup oil (neutral-flavored such as grapeseed or canola, plus additional for oiling the bowl)
4 cup all-purpose flour
2 teaspoon salt
1 1/2 teaspoon pure maple syrup
1 1/2 teaspoon oat milk (or other non-dairy milk substitute)
1/2 teaspoon vanilla extract