Bring 4 quarts of water to a rolling boil in a large pot. Add 2 tablespoons of kosher salt and cook the rotini pasta until just past al dente, about 1 minute longer than package instructions. Drain and rinse under cold water.

In a mason jar, combine olive oil, red wine vinegar, Dijon mustard, honey, dried oregano, salt, and pepper. Shake vigorously for about 30 seconds until well emulsified.

In a large glass bowl, mix cooled rotini, cheddar cheese, halved cherry tomatoes, sliced black olives, diced cucumber, and chopped red onion. Gently fold to combine.

Drizzle half of the vinaigrette over the salad and toss gently until well coated. Taste and add more vinaigrette if needed.

Garnish with fresh basil and extra oregano. Chill for at least 30 minutes before serving.