Puree the pineapple pieces and strain the puree to remove any fiber. Make sure you have 1 cup of fine puree.
Heat 3 cups of milk in a vessel on medium heat; keep stirring every 2-3 mins. After about 30-40 mins, milk will reduce to 75% of its original volume. When it's done, you will have 2 cups of evaporated milk; keep 1 cup for pineapple kulfi and another cup for berry kulfi. To skip this step, you can get canned evaporated milk instead.
Once the milk cools down to room temperature, whisk 1 cup cream, 1 cup evaporated milk, 1/2 cup sweetened condensed milk, pineapple puree together.
Taste the mixture to check for sweetness, add sugar if needed. Pour the mixture into mini dessert bowls, and put them in freezer for 6-8 hours.