In a large mixing bowl, toss together cabbage (7 cups) and drained pineapple (20 ounces); set aside.
In a medium mixing bowl, whisk together mayonnaise (1 cup), half-and-half (1/2 cup), granulated sugar (1/4 cup), and apple cider vinegar (3 tablespoons) until smooth
Add mayo dressing to cabbage and pineapple and toss until well combined. Taste and adjust salt and pepper.
Cover bowl with plastic wrap and refrigerator 1-2 hours before serving.