Lightly spray a bundt cake pan or gelatin mold with cooking spray. Use a paper towel to wipe away any oil that pools in the dish—you want only a fine misting of oil throughout the pan.
Place the crushed pineapple in a fine mesh strainer, and strain VERY well. Use a spatula to press ALL of the liquid out of the pineapple. This is an important step to ensure that the Jell-O sets up in the refrigerator.
Zest the orange and set the zest aside. Peel the orange and roughly chop it. Place the orange in the bowl of a food processor with the apple and fresh cranberries. Pulse until the mixture is the consistency of shredded coconut. Place the mixture in a large bowl.
Bring 2 cups of water to a boil. Whisk in both packages of strawberry Jell-O and the sugar. Add one cup of very cold water and whisk to combine.
Pour the gelatin mixture over the fruit in the large bowl. Stir to combine. Stir in the reserved orange zest.
Transfer the mixture to the greased bundt pan or gelatin mold. Cover the pan loosely with plastic wrap or foil, and place in the refrigerator for at least 8 hours, or up to 48 hours. The gelatin will wiggle slightly when it's ready, but it should not seem wet or soupy.
When you're ready to serve the salad, lightly grease a cake platter or serving dish with cooking spray. This will allow you to move the salad on the plate if necessary.
Place the serving dish on top of the bundt pan/mold, and carefully flip the pan/mold so it's upside down. If the salad doesn't come out of the pan/mold right away, give it a few minutes. You will hear a "plop"!
If the salad still hasn't come out, turn the pan/mold back over, and place it in a few inches of warm water for 15–20 seconds. Then try to invert it again. Continue this process until the salad comes out of the mold.
Garnish with fresh cranberries and orange peel, and serve.