Pineapple Upside-Down Cake Babka

There’s something so nostalgic about a pineapple upside-down cake—the glossy pineapple rings, sticky caramelized brown sugar, and bright maraschino cherries. Now imagine all of that retro charm swirled into a pillowy babka loaf. This Pineapple Upside-Down Cake Babka is exactly that: a mashup of vintage dessert and Jewish comfort baking. It’s gooey, sweet, lightly spiced with cinnamon, and finished with those signature cherries on top. Perfect for a Shabbat table centerpiece, a Friday baking project, or just because you want a babka that makes people say wow.

INSTRUCTIONS

1. Prepare the Dough

Make your challah dough as usual.

2. Roll & Fill

• Divide the risen dough into two equal portions.
• Working with one portion at a time, roll out into a rectangle (about 10x14 inches).
• Spread half the marshmallow fluff evenly over the dough, leaving a ½-inch border.
• Repeat with 1/2 the brown suagr over the marshmallow fluff.
• Sprinkle evenly with half the (well drained) diced pineapple & (optional) cinnamon 

3. Shape the Babka

• Roll up the dough tightly from the long side, just like cinnamon rolls.
• Use a sharp knife to slice the roll in half lengthwise, exposing the filling.
• Twist the two halves together, keeping the cut sides up so the filling shows.
• Transfer to a greased loaf pan lined with parchment paper.
• Top woth halved maraschino cherries 

4. Rise Again

Cover loosely and let the shaped loaves rise until puffy (about 45–60 minutes).

5. Bake

Preheat oven to 350°F (175°C). Bake babkas for 30–35 minutes, or until golden and cooked through. If the tops are browning too quickly, tent with foil for the last 10 minutes. (If a thermometer reads an internal temp of 190f they’re done).

6. Finish & Serve

Once baked, you can brush with a little pineapple syrup for shine or dust with powdered sugar. Slice thick and enjoy while still slightly warm so the filling is soft and gooey.

Storage Tips

• Room Temperature: Wrap tightly and store for up to 2 days.

• Refrigerator: Keep in an airtight container for up to 5 days.

• Freezer: Wrap slices individually and freeze for up to 2 months. Reheat gently before serving.

Ingredient Swaps & Variations

• No marshmallow fluff? Swap for cream cheese whipped with powdered sugar for a cheesecake-like swirl.

• Extra gooey? Drizzle with pineapple syrup from the can before baking.

• Feeling tropical? Add shredded coconut into the filling for extra texture.