Bring a saucepan of water to a boil and drop in your broccoli florets. Cook for three to five minutes until just tender when pierced with a knife. Immediately transfer the broccoli into a bowl of ice water to stop the cooking.
Once the broccoli has cooled in the ice bath, drain it well and pat it dry. Chop it into small, even pieces so it distributes nicely inside the chicken. This keeps every bite balanced with a little bit of everything.
Lay your bacon slices in a large oven-safe skillet over medium heat. Cook until browned and crisp on both sides, about five minutes per side. Set the bacon aside on a cutting board, but leave the flavorful fat in the pan.
Once the bacon has cooled slightly, chop it into small pieces. This bacon will mix in with your broccoli and cheese, so smaller pieces help it roll neatly inside the chicken without falling out.
Slice each chicken breast horizontally to create two thinner pieces. Place them between plastic wrap and pound gently with a mallet until they're about a quarter-inch thick. This makes the chicken pliable enough to roll easily.
Mix your salt, pepper, and smoked paprika together in a small bowl. Sprinkle this seasoning evenly over both sides of each flattened chicken piece. This step ensures flavor throughout, not just in the filling.
Lay out the bacon, broccoli, and shredded cheddar across each chicken piece, leaving a little space at the edges. Starting from one short side, roll the chicken tightly into a log, pressing gently to keep the filling in place.
Secure each rolled chicken breast with kitchen string, tying it at even intervals so it holds its shape while cooking. Trim any excess string so it doesn't get in the way during searing.
Heat the reserved bacon fat in your skillet over medium-high heat. Add the roulades and sear until golden brown on all sides, about five to six minutes per side. This locks in flavor and gives a beautiful crust.
Transfer the skillet to a 350-degree oven and bake until the chicken reaches an internal temperature of 165 degrees Fahrenheit, roughly 15 to 20 minutes. Let the roulades rest for five minutes before slicing.