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Finely chop mushrooms and onion in a food processor. Heat 1 tablespoon oil in a large skillet over medium-high heat. Add the mushrooms and onion, 1/8 teaspoon salt and 1/4 teaspoon pepper; cook, stirring, until the liquid is mostly evaporated, about 4 minutes. Scrape into a bowl and stir in breadcrumbs and cranberries. Wash and dry the skillet.
Cover cutlets with plastic wrap and pound with the smooth side of a meat mallet to about 1/4-inch thickness. Sprinkle one side with poultry seasoning and the remaining 1/4 teaspoon each salt and pepper. Turn the cutlets over and spread about 1/2 cup of the mushroom mixture over each. Roll up, starting from a short side. Tie the rolls closed with kitchen string.
Heat the remaining 1 tablespoon oil in the skillet over medium-high heat. Add rolls, seam-side down, and cook for 2 minutes. Carefully turn. Whisk broth and flour together and add to the pan. Cover, reduce heat to a simmer and cook until an instant-read thermometer inserted into a roll registers 165°F, 10 to 12 minutes.
Remove the rolls from the pan and strain the gravy through a fine-mesh sieve, if desired. Stir in butter until melted. Slice the rolls, if desired, and serve with the gravy.