Preheat your oven to 400 degrees F and line a sheet pan with aluminum foil. Spray it lightly with cooking spray to keep the fennel from sticking. Also, prepare a 3-quart casserole dish by brushing it with melted butter or spraying it with cooking spray. This step ensures that your stuffing will come out perfectly without sticking.
Next, cut the bread into cubes. If your bread is a few days old, it should be fine as is. However, if it’s particularly fresh and moist, consider spreading it onto a sheet pan and toasting it in the oven for 5 to 10 minutes. This will help your bread absorb more of the chicken broth later when baking.
In a large bowl, toss the sliced fennel with melted butter and olive oil. Season with 1/2 teaspoon of both salt and pepper. It’s essential to make sure the fennel is well coated to caramelize evenly. Spread the mixture onto the prepared sheet pan in a single layer.
Bake the fennel for 30 to 35 minutes, stirring every 10 minutes or so. You want it to become soft and caramelized, which enhances the natural sweetness. Once done, transfer the fennel to a large bowl and set aside.
In the same pan, melt 2 tablespoons of butter over medium-high heat. Add the chopped carrots and shallots, cooking until they’re softened, which should take about 10 to 15 minutes. The goal is to have them tender and fragrant.
Add fennel seed, parsley, and thyme to the pan, cooking for 1 minute more to release the herbs’ flavors. Season with a generous pinch of salt and pepper to taste, then transfer this mixture to the bowl with the caramelized fennel.
Return the pan to medium heat and add the Italian sausage. Cook it while breaking up any large pieces until it’s browned, which should take about 5 to 10 minutes. Once cooked, let it cool slightly before transferring it to the bowl with the vegetables.
In a separate bowl or glass measuring cup, whisk together the chicken stock, eggs, and molasses. This mixture will infuse moisture and flavor into your stuffing.
Now, add the bread cubes to the bowl with the vegetables and sausage. Toss everything together to evenly distribute. Pour the liquid mixture over the bread and stir until the bread is evenly absorbed. If you prefer extra moist stuffing, you can add up to another 1/2 cup of chicken broth as needed, but be cautious not to make it soggy.
Finally, pour the entire mixture into the prepared casserole dish, spreading it into an even layer. Bake for 30 to 35 minutes or until the top is golden brown and crispy, and the stuffing is hot throughout. Once done, let it cool for 15 minutes before serving to allow flavors to settle.
