Heat olive oil in a large pot over medium-high heat. Season pork chunks with salt and pepper, then toss in flour to lightly coat. Brown the pork in batches, about 5-6 minutes per batch.Remove and set aside.
In the same pot, add carrots, and potatoes.Cook for 5 minutes until softened.
Add the chicken stock, apples, Italian Seasoning, bay leaf, and browned pork. Bring to a simmer. Cover and cook for 1½ hours, or until the pork is tender and the vegetables are cooked through.
Adjust seasoning with salt and pepper. Remove the bay leaf and serve the stew hot, garnished with fresh herbs if desired.