This is one instance where we like to use canned fruit instead of the fresh stuff because those rings are oh so perfect and just screaming for maraschino cherries. But if you’ve got wicked knife skills, by all means, go ahead and slice and core a fresh pineapple to use. You might want to grab a friend when it comes time to invert: slow cooker inserts can be heavy and you’ll need to hold another plate to catch the cake when you invert it. We think pineapple’s intense sweetness acidity goes very nicely with something creamy and fatty like unsweetened whipped cream.
¾ cup packed dark brown sugar
3 tablespoons unsalted butter, melted
½ teaspoon kosher salt, divided
2 (8-oz.) cans pineapple slices in juice, drained
¾ cup granulated sugar
½ cup canola oil
1 large egg
1 large egg yolk
1 teaspoon vanilla extract
2 cups (about 8½ oz.) all-purpose flour
1 teaspoon baking powder
½ teaspoon baking soda
¼ cup whole milk
How to Make It
Stir together brown sugar, melted butter, and ¼ teaspoon of the salt in a small bowl. Generously coat a 6- to 7-quart round or oval slow cooker with cooking spray. Spread brown sugar mixture evenly in bottom of slow cooker. Arrange pineapple slices over brown sugar mixture, trimming as necessary to make an even layer.
Beat granulated sugar, oil, egg, and egg yolk in a medium bowl with an electric mixer on medium speed until slightly thickened and smooth, about 2 minutes. Stir in vanilla. Whisk together flour, baking powder, baking soda, and remaining ¼ teaspoon salt in a medium bowl. Stir half of the flour mixture into batter until almost incorporated. Add milk, and stir to combine. Add remaining flour mixture, and stir just until incorporated. Spoon batter over pineapples, and spread to edges of slow cooker with an offset spatula.
Drape a clean kitchen towel over slow cooker, and place lid over towel. Pull towel taut under lid. Cook on LOW until a wooden pick inserted in center comes out clean, about 2 hours and 30 minutes. Remove slow-cooker insert to a wire rack, and let stand until cool enough to handle, about 20 minutes. Place a cutting board or serving plate over slow-cooker insert, and carefully invert to release cake. Serve warm or at room temperature.
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