Heat the EVOO in a large skillet over medium-high heat. Add the crumbled Italian sausage and cook until browned about 5–7 minutes. Drain any excess grease and set the sausage aside.
In the same skillet, add the chopped onion and cook until softened about 3–4 minutes. Stir in the minced garlic and cook for another 30 seconds, until fragrant. Then, set aside.
In the same skillet, heat over medium-high heat.
When the skillet is hot, add butter and flour—Cook the roux for 4 minutes. (The roux will turn a light golden color.)
Slowly whisk in the buttermilk, chicken stock, and heavy cream. Stir continuously until the mixture thickens, about 3–5 minutes.
Stir in chopped arugula.
Next, add Italian sausage, onions, garlic, smoked paprika, cayenne pepper, salt and black pepper.
Stir until the mixture is combined. Spoon sausage gravy over fresh-off-the-griddle waffles. Garnish with extra black pepper or fresh herbs, if desired.
Serve!