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Pineapple Tart Rugelach

Lauren Monaco Grossman

On my wedding day, instead of having a wedding cake, I baked hundreds of pineapple tart rugelach. This dessert, which represents the marriage of a Peranakan pineapple tart and a Jewish rugelach, was one of the first ways I celebrated our multiracial and Jewish family through cooking, paying homage to my mother’s Peranakan roots and my husband’s Ashkenazi heritage. (Read about this recipe’s background in my essay “A Pineapple Tart Rugelach 400+ Years in the Making.”)

The great thing about this recipe is that you can bake these in advance and store them in the freezer, which is exactly what I did for our wedding. Our wedding day was free from the stress of last-minute troubleshooting buttercream frosting on a wedding cake, leaving more time to enjoy the day with our friends and family!

2 lbs. of chopped pineapple*
1 star anise or clove
1 cinnamon stick
1-2 pandan leaves, knotted, optional**
½ to ¾ cup sugar (depending on sweetness and size of pineapple)
2 cups (256 grams) all-purpose flour
1/4 cup (32 grams) confectioners sugar, plus extra for dusting
1/2 tsp kosher salt
1 cup (226 grams) cold unsalted butter, cubed
8 oz (225 grams) cold cream cheese, cubed
1 large egg
splash of milk
sugar for sprinkling

For the pineapple jam:

*Fresh pineapple is best but, in a pinch, you can use frozen or even canned pineapple. If using canned pineapple, you may have to cook the jam longer because the pineapple will not be as dry.

**Available at Southeast Asian grocery stores, usually in the frozen section.

To make the pineapple jam: Puree chopped pineapple in a blender until smooth, but not too much, so that there are a few small chunks remaining. In a wok or large pot, combine pineapple puree, star anise, cinnamon stick, and knotted pandan leaves. Cook on high heat until almost dry, around 15 minutes. Add sugar and stir until melted. Continue to cook until the jam lightly browns and becomes thick, around

10-20 minutes. Continue stirring while cooking so the sugar doesn’t burn.

Let jam cool. Jam can be made a few days ahead and stored in the fridge.

For the pastry:

In a food processor, pulse flour, confectioner’s sugar, and salt a few times. Add in cubed cream cheese and butter. Pulse just until coarse crumbs form. Do not overwork dough. The less the dough is handled, the flakier the pastry. Pulse until dough comes together in big clumps. Divide dough into two parts. Wrap each section in plastic wrap. Refrigerate for 4 hours or overnight.

To assemble: Line a large baking sheet with parchment paper. Stack the lined baking sheet on top of another baking sheet to prevent the rugelach from burning on the bottom.

Divide one disk of dough in half. Roll one half of dough onto a work surface dusted with powdered sugar. Dust rolling pin with powdered sugar and roll dough into a circle that is 1/8” thick and about 8-9” in diameter. Dough will be quite sticky.

Spread about 2-3 tablespoons of pineapple jam evenly on top of the dough. Using a pizza cutter or knife, cut dough into four equal wedges. Cut each wedge in half, then half again, for a total of 16 wedges. (If making larger cookies, only cut into 8 wedges). Starting from the outer, wider edge, roll wedge in on itself until you reach the center. If the dough is sticking to your fingers while rolling, dip your fingers in powdered sugar before rolling. Place cookies on prepared baking sheets 1/2” apart, making sure that the points are tucked under the base of the cookie. Refrigerate cookies for about 30 minutes before baking. Scrape work surface clean so there isn’t sticky residue from the previous dough and filling.

Repeat process with remaining dough and filling.

Preheat oven to 350°F.

For the topping:

Mix together egg and a splash of milk to make the egg wash. Brush tops of cookies with the egg wash and sprinkle with sugar. Bake until golden brown, checking after 15 minutes. It may take up to 25 minutes until golden brown.

Remove cookies from baking tray immediately after baking so that the jam doesn’t stick to the baking tray. Let cookies cool on a wire rack. Dust with powdered sugar before serving. Serve at room temperature.

Cookies can be stored in an airtight container for up to one week.

Read about the history of this recipe from author Lauren Monaco Grossman, then sign up to receive The Jewish Dish,’s monthly foodie email.

Lauren Monaco Grossman is a graphic designer and illustrator by day and amateur cook, baker and ice cream maker by night. She graduated from Washington University in St. Louis, where she studied Communication Design and Jewish Studies. She spends her free time watching her sourdough rise and drawing pictures of food.

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