Preheat the oven to 350 degrees F (175 degrees C). Grease a 9x2 1/2-inch round cake pan.

Combine brown sugar and 1/4 cup melted butter in a bowl; spread evenly into the prepared pan. Place 10 pineapple pieces around outer edge of pan, facing the same way, place remaining 2 pieces in the center. Place 1 cranberry between each pineapple piece.

Beat white sugar and 1/2 cup softened butter together in a bowl with an electric mixer until light and fluffy. Add eggs, one at a time, beating well and scraping sides of the bowl after each addition. Beat in baking powder, vanilla extract, almond extract, cinnamon, and salt until combined.

Add flour and milk to batter in 3 additions, adding 1/2 cup flour and 1/4 cup milk at a time, mixing well after each addition, until thoroughly combined.

Pour batter over pineapple slices, making sure batter gets between them. Spread and smooth batter using an offset spatula.

Bake in the preheated oven until a toothpick inserted into the center comes out clean, 40 to 45 minutes.

Cool cake on a wire rack for 15 to 20 minutes. Run a knife around the edges to loosen. Place a plate over pan and quickly invert to release cake, waiting a few seconds and tapping the pan several times if it doesn't immediately separate from the pan.