Preheat an oven to 400 F.
In a large cast iron skillet over low heat, slowly cook the bacon while stirring occasionally until crispy. Use a slotted spoon to remove the bacon from the skillet, while leaving the rendered bacon fat behind.
Add the sausage to the skillet and increase heat to medium. Cook until sausage is browned on both sides and then add the onion. Saute for 2-3 minutes, until the onion is starting to soften.
Add the canned beans, ketchup, hot sauce, 1/3 cup dark brown sugar, dijon, Worcestershire, and the crispy bacon. Bring to a simmer and simmer for 5 min. Remove from the heat and top with the remaining brown sugar.
Transfer the skillet to the oven and bake for 40 minutes, until the top is caramelized and browned. Remove from the oven and serve warm.