Sprinkle the bottom with the brown sugar, and top with the pineapple rings. Place a cherry inside each of the pineapple rings.
Prepare cake mix according to package.
Pour the cake batter on top of the pineapples. Cover and cook on high for 2 - 3 hours. You will know cake is done when it is firm in the center and begins to pull away from the edges.
Turn off crock pot and remove lid. Allow cake to cool for at least 10 -15 minutes before you flip the cake onto a platter.