Prep your pineapple: If using fresh pineapple, cut it into chunks and freeze until solid, at least 4 hours. For speed, use pre-frozen pineapple.
Add to blender: Place frozen pineapple in a high-speed blender or food processor. Add milk, vanilla, and sweetener.
Start with less liquid—you can add more if needed.
Blend in pulses: Pulse to break up the chunks, then blend on low. Scrape down the sides as needed. Add a splash more milk if it’s too thick to move.
Fine-tune the flavor: Taste and adjust.
Add a bit more sweetener if you prefer it sweeter, or a squeeze of lemon or lime for extra brightness. A tiny pinch of salt makes the pineapple pop.
Blend until silky: Keep blending until the mixture is smooth and creamy, like soft-serve. Avoid over-blending to prevent melting.
Serve immediately: Spoon into bowls or pipe through a large star tip for a classic swirl.
Enjoy right away for the best texture.
For a firmer scoop: Transfer to a shallow container and freeze 30–60 minutes, then scoop. If it firms up too much, let it sit at room temperature for 5 minutes.