To make the dough, dissolve the yeast in ¼ cup warm water.
In a separate bowl combine the flax with 8 tablespoons water.
In a microwave-safe bowl, heat the coconut oil and milk until the oil is melted, set aside to cool (115-125˚ F)
Combine the flour, sugar and salt in the bowl of a stand mixer.
Add the milk mixture, yeast, vanilla and flax mixture to the mixer bowl and mix on low until a cohesive dough forms.
Switch to a dough hook and knead for 5-7 minutes until dough clears the sides of the bowl and can be stretched without breaking.
Shape the dough into a round, place back in mixing bowl let rise for 1 to 1 ½ hours.
Once the dough has doubled and does not spring back when indented with a wet finger, gently deflate the dough, shape into a round and let rise for another 30 to 45 minutes in a warm draft-free place. (A front porch of a home stuck in 90˚ F with 100% humidity works wonderfully.)
Gently deflate the dough again, shape it into a round and let sit for 10 minutes. (After the dough has been shaped into a round it can be wrapped in plastic and refrigerated overnight.
Let stand at room temperature 30 minutes before proceeding.)
While the dough rests, mix the cinnamon and sugar together, melt the coconut oil and generously grease an 8x4 loaf pan with shortening.
On a lightly floured surface, roll the dough out to an 18 x 12-inch rectangle.
Brush the dough with the coconut oil then sprinkle the dough with the cinnamon and sugar blend.
With a pastry cutter cut the dough lengthwise into 4, 3-inch strips. Carefully lift each layer on top of the other and line up one cut edge of each strip evenly.
Then with a serrated knife cut the stack of dough into 6 additional pieces (you should end up with layers that are 3x3inch squares.
Place all of the squares into the loaf pan. The pan should be filled edge to edge – if you need to press the dough to make room for all of the dough, do so gently.
Cover the dough with a bread cloth and let rise for 30 minutes.
After 30 minutes, preheat the oven to 350˚ F.
Once the oven is ready put the pan into the oven and bake for 30-35 minutes.
If the dough is browning too quickly, cover the dough loosely with foil.
Remove the pan from the oven and allow it to cool for 20 minutes.
To turn the dough out, run a knife along the edges and either turn the pan upside down or gently push the ends of the loaf together and lift it out of the pan onto a serving platter. Be aware that once you pull the loaf out of the pan, retaining a loaf shape may be difficult