Step 1: In a skillet over medium heat, melt 1 Tbsp of butter. Add the breakfast sausage, breaking it up with a spoon, and cook for 5–6 minutes until browned and fully cooked. Drain any excess fat and transfer the sausage to a clean bowl.
Step 2: While the sausage is still warm, stir in the shredded cheddar until it melts and combines fully with the meat. Set this cheesy sausage mixture aside—this will be your flavorful filling.
Step 3: Trim the crusts off each slice of sandwich bread. On a lightly floured surface, use a rolling pin to flatten each slice into a thin square. Flattened bread rolls more easily and holds the filling without tearing.
Step 4: In a shallow dish or pie plate, whisk together the eggs, milk, vanilla extract, ground cinnamon, and a pinch of salt until fully combined and slightly frothy. This custard-style mixture will soak into the bread, yielding a tender interior and a lightly sweet edge.
Step 5: Lay each flattened bread slice on a clean work surface. Spoon approximately 2 tablespoons of the warm sausage-cheese mixture onto one end of the bread. Fold in the two side edges to enclose the filling, then roll tightly from the filled end to create a neat cylinder, seam-side down.
Step 6: Working one roll-up at a time, gently lower it into the egg dip. Turn to coat all sides evenly, allowing any excess custard to drip off before transferring to a clean plate.
Step 7: Heat a nonstick skillet over medium heat and add a thin layer of butter or spray with nonstick cooking spray. Once the fat is hot, place each roll-up seam-side down and cook for 2–3 minutes per side, turning carefully with tongs or a spatula, until every side is deep golden brown.
Step 8: Remove the cooked roll-ups to a paper-towel–lined plate and let rest for one minute. This brief pause allows any excess oil to drain and the interior to set slightly, making slicing cleaner.
Step 9: Using a sharp knife, trim off any ragged ends then cut each roll-up diagonally into two or three bite-sized pieces. Arrange on a serving platter and drizzle generously with warm maple syrup.