In a medium saucepan over medium heat, combine fresh cranberries with sugar and orange zest, stirring gently until the cranberries burst and the mixture thickens, about 10-15 minutes. Once done, remove from heat and allow your homemade cranberry sauce to cool.

In a large mixing bowl, beat softened butter and brown sugar together until smooth and creamy, about 2-3 minutes. Pour this mixture into the bottom of your greased springform pans, spreading it evenly.

Place the pineapple slices over the caramel glaze in each springform pan, then add a dollop of the cooled cranberry sauce on top, spreading gently with a spoon.

In a separate bowl, cream together softened butter, granulated sugar, and the remaining brown sugar until fluffy, about 3-4 minutes. Add eggs one at a time, mixing well, then fold in orange juice and zest, followed by the dry ingredients.

Spoon the cake batter evenly over the fruit layers in each springform pan and use a spatula to level the batter.

Preheat oven to 350°F (175°C) and bake for 30-35 minutes, checking with a toothpick inserted in the center.

Allow the cakes to cool in the pans for about 10 minutes, then carefully run a knife around the edges and flip onto serving plates.