Preheat the oven to 400°F.
In a large pot, bring potatoes and enough water to cover by 1-inch to a boil over high heat. Cook until potatoes are fork tender. Drain potatoes in a colander and transfer back to the large pot and allow them to steam dry for 5 minutes. Mash with vegan butter, then stir in the plant-based milk until smooth. Cover and set aside.
Meanwhile, heat a large cast-iron pan over medium heat. Add oil, onions, carrots, celery, and thyme. Cook, stirring often until onions are translucent, about 7-10 minutes. Add veggie ground round, break up until crumbly, cook and stir until starting to brown, about 5 minutes.
Stir in tomato paste, cook and stir for 1 minutes, then sprinkle in the flour, cook and stir for 1 minutes. Deglaze the pan with red wine, lifting up any browned bits on the bottom of the pan, cook until the wine has mostly evaporated. Stir in lentils, water, soy sauce, worcestershire, salt, pepper and cinnamon. Remove from heat.
Cover the filling with scoops of mashed potato and spread until smooth and sprinkle with vegan cheese if using. Bake for 30 minutes. If you want to brown the top, turn on your broiler and broil until golden, about 5 minutes. Let rest for 10 minutes before serving.