In a mixing bowl, combine the softened cream cheese and whipped topping (or heavy cream). Using an electric mixer, beat the mixture until it is smooth and creamy. This will take about 2-3 minutes.
Drain the pineapple chunks to remove excess juice. You want the pineapple to be juicy but not too watery, as it could make your trifles soggy. Once drained, you can chop the chunks into smaller pieces if desired.
In your serving cups or jars, start by adding a layer of crushed vanilla wafers at the bottom. Follow this with a layer of the cream cheese mixture, then a layer of pineapple chunks. Repeat the layering process until your cups are filled, finishing with a layer of cream cheese mixture on top.
Cover the cups with plastic wrap or lids and place them in the refrigerator. Allow the Mini Pineapple Cheesecake Trifles to chill for at least 2 hours.
Once chilled, your trifles are ready to be served! You can garnish them with additional whipped topping or a sprinkle of crushed vanilla wafers for an extra touch.
