Pineapple Upside-Down Cake

When an acquaintance commented that one of her favorite foods was her ‘mama’s pineapple upside-down cake’, I knew I’d not rest easy until I made one. So easy, and so good. And, if this was a favorite when growing up, there’s nostalgia in every forkful. There’s a gluten-free option as well, and if you can’t find a gluten-free yellow cake mix, there are instructions for making your own. Run, don’t walk, down memory lane, and get to baking!



1 box yellow cake mix, 15.25 or 18 oz (plus the ingredients for its preparation, usually water, oil or melted butter, and eggs)
1 can pineapple slices (2, if you want complete coverage of a 9″ x 13″ pan)
1/2 stick butter, melted
Brown sugar (enough to cover the bottom of your pan)
Maraschino cherries


Preheat your oven to 350 deg. (see NOTES) Grease a 9″ x 13″ cake pan. Melt 1/2 stick butter, then pour it into the pan, rotating the pan to be sure the butter covers the entire bottom. Then sprinkle brown sugar over the butter, again looking for complete (but not too thick) coverage. (see NOTES)

Place the pineapple slices in the bottom of the pan. If you use a single can of slices, you’ll have 10, and a 3-4-3 pattern is most common. If you have more than a can of slices, you can cover the bottom in a 4-4-4 pattern. Your choice. Place a Maraschino cherry in the center of each pineapple slice.

Prepare the yellow cake mix according to package instructions, pour it over the pineapple and spread for complete coverage.

Bake according to package instructions, testing for doneness with a toothpick. Because of the moisture in the pineapple slices, you may need to bake a slight bit longer.

Once baked, remove from the oven, let it rest for just a few minutes (for sure no more than 10), then invert it onto your serving platter. If a pineapple slice sticks to the pan, remove it and place it where it belongs. Spoon any butter/brown sugar mixture remaining in the pan over the cake.


If you can find a gluten-free yellow cake mix, you can use that and follow the instructions above. Note, however, that some gluten-free cake mixes are not packaged in the same amount as regular cake mixes. You need 15.25 – 18 oz of cake mix.

If you are unable to find a gluten-free boxed mix, you can make your own here.


When baking with a boxed cake mix, take note of any instructions regarding oven temperature adjustments tied to the type pan being used. Some will recommend a lower temperature when using non-stick or glass pans.

Once you put the melted butter in the pan, if you have time to let it cool and set up, you will find it easier to spread the brown sugar more evenly in the pan.

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