Combine crushed pineapple (with juice) and additional pineapple juice in a blender. Blend on low until fully incorporated.
Add the whipping cream and optional vanilla extract and pulse until well mixed. For a frothier popsicle, you can increase to a full blend to give it a light whipped texture.
Taste and add additional whipping cream, if desired.
Pour into molds and allow to freeze at least five hours or overnight before serving.
**For a sweeter popsicle, add 2 Tbsp sweetened condensed milk to mixture
