Easy Breezy Pineapple Upside Down Cake

This delicious recipe is a remake from Woman and the Whisk and it is absolutely amazing!

This puts every other Pineapple Upside Down Cake to Shame

Tip: Let this cake sit in the fridge over night and enjoy cold the next morning and it will be bursting with that amazing pineapple flavor!


  • 3/4 cup Butter = (1 1/2 sticks)
  • 1 1/4 cup packed Brown Sugar
  • 1 tsp Vanilla Extract
  • 1 can (20 oz.) Pineapple slices in juice (drained, reserve juice)
  • 3/4 cup crushed pineapple
  • 1 jar (6 oz.) Maraschino Cherries without stems (drained)
  • 1 box of Betty Crockers Super Moist Yellow Cake Mix (vegetable oil and eggs as called for on cake mix box)

Cooking Tools

  • 9×9 non-stick pan
  • Measuring cups/spoons
  • Toothpick

How to make: Easy Breezy Pineapple Upside Down Cake

Preheat oven to 350°F (325°F for dark or nonstick pan). In 13×9-inch pan, melt butter in oven. Sprinkle brown sugar evenly over butter. Arrange pineapple slices on brown sugar. Place cherry in center of each pineapple slice (if you wipe off the excess juice from the cherries, this prevents the red from bleeding into the pineapple slices.), and arrange remaining cherries around slices; press gently into brown sugar.
Add enough water to reserved pineapple juice to measure 1 cup. Make cake batter as directed on box, substituting pineapple juice mixture for the water, add vanilla and crushed pineapple, mix.  Pour batter over pineapple and cherries.
Bake 42 to 48 minutes (44 to 53 minutes for dark or nonstick pan) or until toothpick inserted in center comes out clean. Immediately run knife around side of pan to loosen cake. Place heatproof serving plate upside down onto pan; turn plate and pan over. Leave pan over cake 5 minutes so brown sugar topping can drizzle over cake; remove pan. Cool 30 minutes. Serve warm or cool. Store covered in refrigerator.

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