Last year, I posted a recipe called Easiest Ever Mango Sherbet. The gist is that you blend frozen fruit and a can of sweetened condensed milk, then freeze it and scoop it like regular sherbet/ice cream…but you don’t have to have an ice cream machine, you know? And that’s ideal because I think if I bring another piece of equipment home, my beloved roommate will abandon me and I’ll have to build a house out of all my cake pans.

But I digress.

Today, I took that easy formula and complicated it in the very best way: the Pineapple Upside-Down Cake way! That’s right—all the flavors that you love in the undisputed queen of everyday cakes are packed into this cold, creamy, scoopable treat! The base is buttery brown sugar-roasted pineapple bliss, and every bite is filled with bits of vanilla cake, maraschino cherries and butterscotch sauce!

Pineapple Upside-Down Cake Sherbet starts with a whole pineapple. You could, of course, do this with about 2 1/2 pounds of pre-cut pineapple, but buying whole is much cheaper. Don’t fret—I’ve detailed how to slice up a pineapple in the recipe.

Once it’s sliced up, the pineapple is brushed with melted butter & brown sugar and roasted until tender, fragrant, and rich yellow in color. This concentrates the flavor and softens the fruit’s natural tartness. Also, it smells out-of-this-world good. Please resist eating half of it in one sitting so you can make it into no-churn sherbet, okay?!

After roasting, let your pineapple cool before freezing it. The sherbet base requires only frozen fruit and sweetened condensed milk—don’t try to take any shortcuts here! I find it easiest to freeze the pineapple by arranging it in one layer on a small sheet pan, then freezing until…well, frozen. You can do this a few days (or even weeks!) in advance; just transfer your frozen roasted pineapple into a freezer bag for longer storage.

Next up: blend the base! This is easy. Just combine your frozen roasted pineapple and sweetened condensed milk in a blender and blitz away! Pour half the creamy, pale yellow mixture in a loaf pan, then top it with Pineapple Upside-Down Cake mainstays like maraschino cherries, cubes of vanilla cake, and spoonfuls of brown sugary butterscotch. Repeat the layering with the remaining pineapple base and toppings and then freeze until scoopable. Finish it with more butterscotch and cherries, if desired. Pineapple bowl optional, but recommended.

One quick thing before I get to the recipe. This recipe has a lot of steps, but can be as easy or as complicated as you like. For instance, I baked my own vanilla cake and made a batch of butterscotch for this sherbet, but this recipe would work just as well with store bought pound cake and jarred butterscotch (or caramel sauce or dulce de leche). As with all the recipes on this site, we’re aiming for delicious and fun here. If making the base, some cake and butterscotch ceases making this process enjoyable, by all means take some shortcuts.

I won’t tell anyone. I’ll be too busy shoving bites of Pineapple Upside-Down Cake Sherbet into my face to even care.

Pineapple Upside-Down Cake Sherbet
makes about 8-10 servings

Roasted Pineapple:
1 whole pineapple (about 4 lbs)
3 tablespoons unsalted butter, melted
2 tablespoons light or dark brown sugar, packed
pinch of Kosher or sea salt

For the Sherbet Base:
1 14-ounce can sweetened condensed milk

For Assembly (all divided):
2/3 cup maraschino cherries, drained & cut into small pieces
3/4-1 cup butterscotch sauce (or caramel sauce)
1 1/2 cups 1/2-inch vanilla cake cubes (cake recipe below)

Roast the pineapple. Preheat the oven to 400F. Line a rimmed sheet pan with parchment. Set aside.

Place your pineapple on its side on a cutting board. Use a large, sharp chef’s knife to lop off the top & bottom. Move the pineapple so that it is standing on the flat spot where the bottom used to be. Use the knife to remove the rind (skin) in strips, being sure to also remove the brown dots beneath it. Slice around the core, then discard it so that only the flesh (good fruit) remains. Slice your pineapple flesh into spears, and then split each spear into 2 shorter spears. Place them in an even layer on the prepared sheet pan.

Place butter and brown sugar in a small microwave-safe bowl. Microwave in 30 second increments, stirring in between, until butter is melted and mixture is combined.

Brush half the butter & brown sugar mixture on the pineapple pieces. Roast pineapple 20 minutes. Flip the pieces and brush with remaining butter & brown sugar. Roast another 20 minutes. Cool pineapple completely.

Freeze the roasted pineapple. Line a rimmed sheet pan that will fit in your freezer with parchment. Arrange roasted pineapple pieces in one layer on the pan, then place the pan in the freezer for at least four hours or overnight. If not making sherbet immediately, remove frozen roasted pineapple to a freezer bag before returning to the freezer.

Make the sherbet base. Combine frozen roasted pineapple and sweetened condensed milk in a high-powered blender. Blend on high for about 1 minute, or until smooth and thick. Use a silicone spatula to scrape down the sides of the carafe as necessary.

Assemble the sherbet. Transfer half the sherbet base to a loaf pan or other vessel. Scatter with half the maraschino cherries and cake cubes. Drizzle on butterscotch sauce, or drop on by the spoonful. Top with remaining sherbet base, spreading it to the edges to cover the add-ins. Top with remaining cherries, cake cubes & butterscotch. Freeze 4-6 hours before scooping and enjoying.

Pineapple Upside-Down Cake Sherbet will keep covered in the freezer for up to a month.

Vanilla Cake
makes 1 9x5” layer

3/4 cups all-purpose flour
1 tablespoons cornstarch
1/4 teaspoon baking powder
1/8 teaspoon baking soda
1/2 teaspoon Kosher or sea salt
1/4 cup (1/2 stick) unsalted butter, softened to room temperature
1/4 cup granulated sugar
1/4 cup light brown sugar, packed
1 large eggs, room temperature
1 teaspoons pure vanilla extract
1/2 cup buttermilk (not skim or fat free), room temperature

Preheat oven to 350F. Grease a 9x5-inch loaf pan. Line with parchment, leaving some overhang on the two long sides for easy removal. Grease again. Set aside.

Make the cake batter. In a small mixing bowl, whisk together flour, cornstarch, baking powder, baking soda, salt, granulated sugar and light brown sugar. Set aside.

In a medium mixing bowl, cream butter with an electric mixer until light and fluffy, about two minutes. Beat in the egg. Mix in half the dry ingredients, followed by half the buttermilk. Add remaining dry ingredients followed by the remaining buttermilk. Scrape down the bowl as necessary.

Pour batter into prepared pan. Tap full pan on the counter five times to release any large air bubbles. Bake cakes 33-37 minutes, or until a toothpick inserted in the center comes out clean. Let cake cool in its pan for fifteen minutes. Use parchment overhang to lift cake onto a rack to cool completely. Peel off and discard parchment.

For Pineapple Upside-Down Cake Sherbet, you will only need about half this cake (1 1/2 cups 1/2-inch cubes). Use the other half for snacking, or triple wrap in plastic and freeze for up to 3 months.