Heat oil in a large dutch oven over medium-high heat. Add diced bacon and cook until crispy and golden. Remove bacon with a slotted spoon and set on paper towels to drain excess grease. Drain all but 1-2 tablespoons of oil.
Add Italian sausage and crumble as it cooks. Add diced onion and minced garlic. Continue cooking until the sausage is no longer pink. Sprinkle in flour.
Stir to combine so everything in the pot is coating. Pour in water then stir in Yondu Vegetable Umami Seasoning and diced potatoes. Bring to a boil, then reduce heat to a more gentle boil.
Cook for about 15 minutes, until potatoes are fork-tender. Stir in pesto, heavy cream, parmesan cheese kale, and about half of the bacon, saving the rest of the bacon for topping. Cook until kale is wilted, about 3 minutes. Season to taste with salt, pepper, and red pepper flakes if desired.
Serve Zuppa Toscana immediately and top with crumbled bacon, a sprinkle of parmesan cheese, and freshly cracked pepper.