Begin by draining the crushed pineapple thoroughly in a fine mesh strainer. Use the back of a spoon to press out any excess juice, ensuring it's well-drained.

Transfer the pineapple to a large mixing bowl and add the cherry pie filling, sweetened condensed milk, and thawed whipped topping.

Mix ingredients gently with a spatula until the mixture is uniformly pink, about 2-3 minutes.

Continue folding until you achieve a light and airy texture, about 1-2 minutes.

Cover the mixing bowl with plastic wrap or transfer to an airtight container and refrigerate for at least 30 minutes.

Before serving, give the fluff a gentle stir and fold in any optional ingredients as desired.