Add the cherry jello into 2 cups of boiling water, stirring for 1 minute until dissolved. Add the cherry pie filling and crushed pineapple with its juices and stir to combine.

Pour into a 9x13-inch pan and carefully transfer to the fridge to set for 3-4 hours.

In a large bowl, whisk the vanilla pudding powder with the cold milk for 1 minute, then let it sit for 2 minutes to set up.

Meanwhile, beat the heavy cream with a hand mixer or stand mixer fitted with the whisk attachment until soft peaks form. Add the powdered sugar and continue to beat until stiff peaks form, but be careful not to overbeat and turn it into butter.

Fold the whipped cream into the vanilla pudding until combined. Spread evenly over the set jello, then refrigerate until ready to slice and serve.