Open the smaller, 8 oz. can of crushed pineapple. Strain the pineapple juice from the crushed pineapple into a 2 cup measuring cup. Reserve the crushed pineapple for mixing into the whipped cream.
Add enough milk to the measuring cup to reach 1 ½ cups (360 ml) total liquid. Make the vanilla pineapple pudding by whisking the box of vanilla pudding mix with the milk and pineapple juice until thicken, smooth and well combined.