Wake up yeast: Microwave almond milk for about 40 seconds. Should be lukewarm. Add a pinch of sugar and one yeast package. Mix until combined and let sit for 10 minutes. Yeast will be bubbly and frothy when ready.
In a large mixing bowl add vanilla, butter, and active yeast bath. Stir to combine.
In a separate mixing bowl, whisk together flour, sugar, salt, and chai spice. Add half of the flour mixture to wet mixture and stir with rubber spatula. Add the remaining flour and stir until just combined. The dough might look floury and that is okay!
Transfer dough to a lightly floured surface and knead for 10-15 minutes. Only add more flour if the dough begins to stick to the surface or your hands. When the dough is ready, it will be slightly sticky and spring back when you press it.
To Make the Filling:
In a small bowl, mix softened butter, sugar, cinnamon, and chai spice. The mixture should be smooth and spreadable.
Remove plastic wrap and punch dough to release the air. Transfer to a floured surface and roll into a 9x13" rectangle. The dough will be about 1/2 inch thick.
Add filling and smooth out with a rubber spatula. Add pecans (optional). Roll tightly starting from the shorter side. Push in the sides as you roll so it stays uniform.
In a small mixing bowl, whisk all ingredients together. Add more almond milk until desired consistency is reached. Add more powdered sugar if icing is too liquidly.
Using dental floss, cut the dough into 12 even pieces. Place in greased pan. I grease my pan with the empty butter wrapper! Cover with a towel and let sit for 45 minutes. If you want to make these rolls in advance, now is a good step to stop. You can keep unbaked rolls covered in the fridge overnight or in the freezer for 6 weeks.
Preheat the oven to 350 degrees Fahrenheit.
Bake for 30-35 minutes. Remove from oven and let cool before adding icing.
To Make the Icing:
Add a small amount of oil to a clean bowl to coat the bottom and sides. Add dough and give it a swirl around the bowl so all sides are covered in oil. Cover the bowl with plastic wrap and let rise for 1 hour. The dough should double in size.
Pour icing over baked and slightly cooled cinnamon rolls. Serve warm. Leftovers keep in the fridge for about 1 week.