Combine olive oil, vinegar, sugar, salt, pepper and 2 tablespoons dried cranberries in a small food processor. Pulse until cranberries are small and dressing is emulsified. Allow to set at room temperature for 30 minutes to let the flavors meld. Whisk once more before using.
Add a ring of Eckrich Polska Kielbasa to a pan of boiling water. Boil 3-5 minutes or until warmed through.
Place a bed of arugula on a plate, cut cherry tomatoes in half and sprinkle onto arugula. Top with ring of sausage, drizzle with pre-made dressing and finish off with a sprinkle of dried cranberries.