Pineapple Tart Rugelach

Makes 64 bite-sized cookies
or 32 larger cookies

I made these cookies for our wedding! This cookie is the marriage of a Jewish rugelach pastry and a Peranakan pineapple tart. Read the story behind the cookies here. It’s best to break this recipe up into a couple days. You can make the jam and dough ahead of time and store in fridge.

2 pounds of chopped pineapple*
1 star anise or clove
1 cinnamon stick
1-2 pandan leaves, knotted, optional**
1/2 - 3/4 cup (104-156 grams) 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

*Fresh pineapple is best, but you can also 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.

Puree chopped pineapple in a blender until finely chopped, but still has a few small chunks. In a wok or large pot, combine pineapple puree, star anise, cinnamon stick, and knotted pandan leaves. Cook over high heat until it begins to bubble, then reduce to medium heat and stir occasionally. Continue cooking until it starts to deepen in color and becomes almost dry (this can take 20-40 minutes). Reduce to low heat and add sugar and stir until melted. Continue stirring while cooking so sugar doesn’t burn. Cook until the jam caramelizes and becomes thick, around 10-20 minutes. You should be able to see the bottom of the pot when you stir the jam.

Remove from heat and let cool. It will thicken up slightly. Remove pandan leaves and spices. Jam can be made a few days ahead and stored in the fridge.

In a food processor (or use a dough cutter), pulse flour, powdered 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.

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 1/8th” thick and about 8-9” in diameter. Dough will be quite sticky. The edges of the dough do not need to look perfect, since they will be rolled up and won’t be seen.

Spread about 2-3 tablespoons of pineapple jam evenly over top of 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.

Mix together egg and splash of milk to make egg wash. Brush tops of cookies with 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 1 week. They also freeze well.

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