Happy National Pineapple Upside Down Cake Day!

This is the most ridiculous “day” ever. However, we have kids (hence, the name paleoPARENTS.com). Kids love cheesy holidays. So, when I (yes, this is a rare Stacy recipe!) found out that today was National Pineapple Upside Down Day I knew Cole (who lists pineapple as one of his top 3 favorite foods of all time) would want to celebrate.

With dinner guests already scheduled to come over (long-time blog readers and book owners will remember James & Brady from Hot Pot), I reached out to see if they’d mind grabbing a pineapple on their way. Of course they wanted cake!

Once they arrived, Liz and I (once again) entered the test kitchen – and (once again) magic happened! In case you’re wondering, we did not succeed on the first try – don’t think magic cake happens without experimentation! Luckily, we experiment so you don’t have to.

Pineapple Upside Down Cake


  • 2 Tablespoons coconut oil
  • 1 C palm sugar
  • 1 C water
  • 2 tsp baking soda
  • 1 fresh pineapple (optional)
  • 1 can pineapple rings, divided:
    • 1/2 C diced pineapple
    • 2 Tbsp pineapple juice
    • remaining rings if not using fresh pineapple noted above
  • 1/2 C coconut oil, liquified
  • 2 eggs
  • 1 Tbsp vanilla


  1. ♥ Grease bottom of 9×13 pan with coconut oil
  2. Bring palm sugar and water to a boil in a saucepan over high heat, stirring occasionally (about 5 minutes)
  3. Add baking soda and stir quickly off the heat to thicken (Eat Like a Dinosaur owners will recognize this as a version of the caramel sauce)
  4. ♥ Meanwhile, prep your pineapple. Drain the juice from the pineapple and set aside. If using a fresh pineapple too (recommended) slice into 1/2″ rounds. We used an apple corer to make them have that pretty, perfect look – they also sell this fancy tool.
  5. Pour warm, thick “caramel” sauce into cake pan of your choice (we used an 9×13 cake pan).
  6. ♥ Lay your pineapple rounds (canned or fresh, your choice) down at the bottom of your cake pan. The more you can cram in, the better. No one wants a piece without pineapple on top!
  7. ♥ Combine the 2nd set of (wet) ingredients in a food processor – use only 1/2 cup pineapple and 2 tablespoons of pineapple juice and save the rest for adding to water or other refreshing drinks!
  8. ♥ Add the 3rd set of (dry) ingredients to the food processor, and pulse until just combined.
  9. ♥ Gently spread the cake batter over the pineapple rings.
  10. Bake for 25-30 minutes at 350 degrees.
  11. Once cooked, let your cake sit for 5 MINUTES (no longer, no shorter) before “flipping” onto large serving dish.
  12. I dare you not to enjoy!

As always, steps are eligible for munchkin participation!

This is an impressive dish that’s really not much effort at all. Whether it’s being served at a Mad Men themed cocktail party or a kids’ birthday – it will be enjoyed. It would serve around 8-10 people, if you can hold yourself back from 2nds.


You Might Also Like

Switch with Stacy and Use CLEANFORALL20 for 20% off!Shop with Stacy Toth HERE