Flatten the Chicken – Thoroughly dry each piece with a paper towel. Place one between two sheets of plastic or inside a large plastic bag and flatten to an even ¼-inch thickness. Repeat with the remaining pieces.
Roll the Chicken – Layer two slices of ham and ¼ cup of swiss cheese on top of each flattened piece of chicken. Starting at the shorter end, roll tightly, tucking in the sides, to create a cigar shape. Tightly cover each roll in plastic wrap, twisting the sides to secure it. Refrigerate them for 30 minutes or freeze them for 15 minutes to firm up.
Preheat the Oven – Set the oven rack to the middle position. Heat to 450°F (230ºC). Line a large baking sheet with foil and lightly grease it with olive oil, spreading to evenly coat. Set aside.
Set up the Breading Station – In one shallow bowl, mix the flour with 1 teaspoon kosher salt, and ½ teaspoon black pepper. In a second
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