Crush the biscuits into fine crumbs. Make sure the crumbs are even and not too coarse. Add melted butter slowly and mix until the crumbs are fully coated and slightly sticky. Set aside.
Add crushed pineapple, sugar, and pineapple juice to a pan. Cook on low to medium heat while stirring. Let it simmer until it thickens slightly and most of the extra liquid is reduced. Remove from heat and cool completely before using.
In a mixing bowl, beat softened cream cheese until smooth and creamy. Add powdered sugar and vanilla extract. Mix well until fully combined and free of lumps.
Gently fold whipped cream into the cream cheese mixture. Use a spatula and fold slowly to keep the mixture light and airy. Do not overmix.
Take serving jars and add a layer of biscuit crumbs at the bottom. Press lightly with a spoon to form a base layer without making it too hard.
Add a layer of cheesecake cream over the biscuit base. Spread evenly to cover the crumbs completely.
Spoon a layer of cooled pineapple mixture over the cream layer. Spread gently without mixing the layers.
Repeat the layers again with biscuit crumbs, cheesecake cream, and pineapple mixture. Adjust the number of layers based on jar size.
Finish with a top layer of pineapple. Smooth gently for a clean look.
Refrigerate the jars for at least 2 hours. For best texture and flavor, chill longer before serving.