Lightened Up Pineapple Upside Down Cake
A little less guilt means you can have another slice, right? Try this Lightened Up Pineapple Upside Down Cake!
Dish Count :: 1 Mixing Bowl, 1 Small bowl, 1 Skillet, 1 9″ Cake Pan

The out of office notifications were sent out. Most were accepted. One was not. It came back with the response, “This vacation is declined. It will only be approved upon receiving a pineapple upside down cake.” Did I mention that we are off to Hawaii in the morning?
Now, I spoil the guys at work. Spoil them. The weekends baking projects inevitably find themselves back in the office with them hovering over them, or hacking off one little bit at a time pretending like one bit isn’t going to derail the diet or they can tell their wives “hunny, I didn’t have a whole doughnut today…”
But since I will be gone for a week and a half, I figured this one request could be accommodated. And a lightened up pineapple upside down cake had been on my must make list for ages. I just didn’t need to tell them that.

This is going to be Ben’s first time in Hawaii, and we are both getting really excited! It’s been a long time since I’ve been there, and I’m excited for all the beaches, snorkeling and did I mention beaches? Ben? Not snorkeling, not swimming and not water. Homeboy doesn’t swim!! But we did find a kiddie pool style bay that we can hit up to take him snorkeling at. I’m determined to get him in the water and not let him get eaten by a shark.
Imagine all the Nemo’s and Dory’s we will meet! I can’t wait! So many exclamation points.
So, today I will muddle through this last day of work, and try to keep my head in the game for 8 more hours. Send prayers. It’s going to take a lot of them. Or maybe another slice of lightened up pineapple upside down cake.
Fine, two.
Be sure to follow along on our trip on Instagram! We will be chronically the whole trip there, and coming back here through the adventure to give you recaps.

The recipe I used for this recipe is from America’s Test Kitchen’s Comfort Food Makeover Cookbook. I used sweet cream butter because that was all I had, and I highly recommend following the directions with unsalted butter, as the sweet cream contained just enough salt to be slightly noticeable. You may notice, or you may not. I noticed, so just be warned. Also, they recommend using frozen pineapple. My store did not carry frozen pineapple, so 2 large cans of pineapple tidbits, drained, did the tricks.
Carry on!
How to Pick the Perfect Pineapple
Lightened Up Three Cheese Alfredo – another lightened up comfort food!
Cast Iron Skillet Pineapple Upside Down Cake – Made all in a skillet!
Lightened Up Pineapple Upside Down Cake
A little less guilt means you can have another slice, right? Try this Lightened Up Pineapple Upside Down Cake!
- Prep Time: 25 minutes
- Cook Time: 25 minutes
- Total Time: 50 minutes
- Yield: 8
- Category: Dessert
- Method: Baked
- Cuisine: American
Ingredients
Pineapple
- 2 Large Cans Pineapple Tidbits, drained
- 1/3 cup Brown Sugar
- 2 Tbsp Unsalted Butter
- 2 tsp Lemon Juice
- 1/2 tsp Vanilla Extract
Cake
- 1 cup Flour
- 1 tsp Baking Powder
- 1 tsp Salt
- 1/2 cup Sour Cream
- 1/2 cup Sugar
- 1/4 cup Brown Sugar
- 2 Eggs
- 1 1/2 tsp Vanilla
- 4 Tbsp Unsalted Butter, melted and cooled
Instructions
For the Pineapple
- Preheat the oven to 350 degrees.
- In a skillet, combine pineapple and brown sugar over medium high heat and cook, stirring often, until the pineapple is light brown and the juices are nearly evaporated. This will take about 12 minutes.
- Remove from the heat and add butter, vanilla, and lemon juice.
- Pour the pineapple into a 9 inch cake pan that has been sprayed with non-stick spray. Spread the pineapple out on the bottom of the pan into a single layer. If there is excess pineapple, remove from the pan and set aside.
For the Cake
- In a small bowl, whisk together the flour, baking powder, and salt.
- In the larger mixing bowl, whisk together the sour cream, sugar, brown sugar, eggs, vanilla and butter. Gently stir in the flour until just combined.
- Pour over the pineapple in the cake pan and bake for 25-27 minutes, or until a toothpick inserted in the center comes out clean.
- Let cool in the pan for 10 minutes, and then invert on a plate and release from pan. Top with extra pineapple if there was any.
- Wait for 1 hour for cake to cool before serving.
Notes
To store: Pineapple upside down cake should be stored in the refrigerator. Wrap it in the cake pan or place it in an airtight container; it will last up to 3 to 4 days in the fridge.
To freeze: Once the cake has cooled, it can be wrapped and frozen for up to 3 months. Let the cake thaw in the refrigerator before serving.
Recipe mildly adapted from America’s Test Kitchen’s Pineapple Upside Down Cake
Keywords: upside down cake, easy pineapple upside down cake, homemade pineapple upside down cake
Now, this is what I’m talking about!! Pass me a slice….or three, please?!
Have so much fun!!! Both my husband and I have never been to Hawaii, it’s totally our next stop! And this cake??? I second Lauren — I’ll take three please!
This is exactly what I need right now! I am only a few days into a diet and I am craaaaaaaving sweets. This is the perfect way to stay on track and get my sugar fix!
Pineapple upside down cake is one of my favorite desserts. Mostly I just enjoy eating the top (/bottom?). Have SO much fun on your trip. Can’t wait to see pictures!!!!
I was joking with Julie Ruble yesterday that I am convinced anyone that makes anything with pineapple or coconut made it for me. ha ha. You do know this is my favorite cake in the whole world right? I am going to have to make your version soon. So good. And have a blast in Hawaii!! We are going for a couple weeks this summer. Can’t wait!
Say what! I need to come work with you.. 🙂 and OMG Hawaii, I’ll totally jealous of you right now. Have so much fun and please send me a slice (or 5) of this cake.
I love pineapple upside down cake! And this recipe looks perfect. Definitely digging the “lightness” of it.
Love this lightened up Pineapple Upside Down Cake!! Gorgeous!
HAVE SO MUCH FUN IN HAWAII!!! So. Dang. Jealous!
Eeeek! Have fun! I’m so excited for you. Can’t wait to see pics! XO
Hawaii + cake = WINNING.
Ahhhh! So jealous of your trip! Have tons of fun!
Yes! This is exactly the sunny dessert my gloomy weekend needs. Enjoy some sun for me in Hawaii! And a few mai tais too. 🙂
Loving this pineapple upside down cake! So happy I can have second slice without feeling guilty! Hope you have an awesome vacation! Hawaii is one of my favorite places to visit!
I’ve never had pineapple upside down cake, but this looks so amazing and I love the lighter version 🙂
I totally spoil my co-workers, too! It’s just my boyfriend and I at home so when I make treats and snacks, there’s way too much for us. So I brings tons of goodies to work for the co-workers. I need to try your pineapple upside down cake – 1. because it looks crazy good. 2. because I know my co-workers would love me forever if I brought this in to them!
Have a great time in Hawaii. <3
Oooh, a lightened version of Pineapple Upside Down cake… intrigue! This is my boyfriend’s favourite cake, so he’ll be pleased. Thanks for the great recipe!
Hi! Just wanted to let you know that on your recipe for Lightened Up Pineapple Upside Down Cake on your website http://www.countrycleaver,com/2015/01/lightened-up-pineapple-upside-down-cake.html, the ingredients for the pineapple section have an error in the recipe. Look at the vanilla, it says 1/2 Vanila. 1/2 what?? I assumed it was 1/2 tsp. vanilla and not 1/2 Tbsp. Vanilla. Correct??
Thanks so much,
Annie
Did you receive a response on the vanilla amount for this recipe?
Hi Nancy, so sorry I missed this comment!! Add 1 tsp Vanilla.
I saw the same issue with the vanilla. Did you receive a response as to the amount of vanilla to use? Awesome recipe!
What about the lemon? It’s listed in ingredients but the instructions don’t mention when to add it… Thank you!
Oh goodness! I’ll get it added! I apologize!