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.
Notes
Use freshly shredded cabbage if you want the crunchiest texture possible.
Add the dressing gradually if you prefer a lighter-coated slaw.
Make it slightly ahead — pineapple coleslaw often tastes even better after a few hours in the refrigerator.
For extra sweetness, add a spoonful of pineapple juice to the dressing.
For more savory balance, stir in sliced green onions or a little celery seed.