Season & Dust Cutlets: Pat chicken cutlets thoroughly dry with paper towels. In a shallow bowl, whisk flour, garlic powder, onion powder, salt, and black pepper. Dredge each cutlet lightly in the flour mixture, shaking off any excess.
Golden Pan-Sear: Heat 2 tablespoons olive oil and 1 tablespoon butter in a large 12-inch cast-iron skillet over medium-high heat until shimmering. Sear chicken cutlets in a single layer for 3 to 4 minutes per side until deeply golden brown and an internal meat thermometer registers 165°F (74°C). Transfer seared cutlets to a warm plate and tent loosely with foil.
Sauté Aromatics & Deglaze: In the same skillet, reduce heat to medium. Melt the remaining 1 tablespoon of butter. Add sliced garlic and fresh chopped rosemary, sautéing for 60 seconds until fragrant. Pour in aged balsamic vinegar, using a wooden spoon to scrape up all the delicious caramelized brown bits (fond) from the bottom of the pan.
Simmer Cranberry Glaze: Stir in pure maple syrup, Dijon mustard, chicken bone broth, and fresh cranberries. Bring to a vigorous simmer and cook for 4 to 6 minutes, stirring occasionally, until cranberries begin to pop, soften, and release their rich ruby juices into a thickened, glossy glaze.
Nestle & Glaze: Nestle the seared chicken cutlets and any resting plate juices back into the skillet directly into the bubbling cranberry sauce. Spoon generous ladlefuls of glistening cranberries and pan reduction over each cutlet. Simmer gently for 2 minutes to reheat through.
Garnish & Serve: Remove skillet from heat. Garnish with fresh rosemary sprigs and freshly cracked black pepper. Serve warm straight from the skillet alongside roasted garlic mashed potatoes and buttered green beans.