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Pineapple Tart Rugelach

Lauren Monaco Grossman

Medium

Difficulty

I made these cookies for my wedding; they bring together my mother’s Peranakan side, and my husband’s Ashkenazi heritage. A marriage of Jewish rugelach and pineapple tarts, they’re a cookie full of history and culture. 

Pineapple tarts are bite-sized treats found in Singapore, Malaysia and Indonesia. They’re popular in Singapore all year round, but especially during Lunar New Year, Deepavali and Hari Raya. The pineapple tart itself has cross-cultural origins, harmonizing Southeast Asian spices with pineapples that were brought over to the area by the Portuguese, and a short, tart pastry with roots from European colonial influences. 

The pineapple jam works beautifully with a cream cheese rugelach dough. Rugelach dough was traditionally made with yeast in Poland, Ukraine and Russia. Jewish bakers arriving in the United States made use of cream cheese, which became widely available in the late 1800s, and the cookies took on a flakier texture. The crumbly, flakiness of the cookie is a perfect match for the pineapple jam. 

The recipe can be broken up and each component can be made ahead of time, and even frozen until you are ready. The baked cookies can also be easily frozen. 

Ingredients for 64 bite-sized cookies or 32 larger cookies

Pineapple Jam 

  • 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) 

*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. 

Pastry 

  • 1 cup (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 

Topping 

  • 1 large egg
  • splash of milk
  • sugar for sprinkling 

rugelach rolling

Directions

Pineapple Jam

  1. Puree chopped pineapple in a blender until finely chopped, but still slightly chunky. 
  1. 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.  
  1. Continue cooking until it starts to deepen in color and becomes almost dry (this can take 20-40 minutes).  
  1. Reduce to low heat and add sugar and stir until melted. Continue stirring while cooking so sugar doesn’t burn.  
  1. 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. 
  1. 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. 

Pastry 

  1. In a food processor (or use a dough cutter), pulse the flour, powdered sugar and salt a few times.  
  1. Add in cubed cream cheese and butter. Pulse just until coarse crumbs form and dough comes together in big clumps.  
  1. Take the dough out of the food processor and knead it slightly, just enough to bring it together. Do not overwork it! The less the dough is handled, the flakier the pastry.  
  1. Divide dough into two parts. Wrap each section in plastic wrap. Refrigerate for four hours or overnight. 

 How to Assemble

  1. 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. 
  1. Divide one disk of dough in half. Roll one half of dough onto a work surface dusted with powdered sugar.  
  1. Dust rolling pin with powdered sugar and roll dough into a circle that is 1/8-inch thick and about 8-9 inches 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. 
  1. Spread about 2-3 tablespoons of pineapple jam evenly over top of dough.  
  1. 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 eight wedges.)  
  1. 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.  
  1. Place cookies on prepared baking sheets 1/2-inch apart, making sure 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. 
  1. Preheat oven to 350°F. Mix together egg and splash of milk to make egg wash. Take the cookies out of the fridge and brush the tops with egg wash and sprinkle with sugar. Bake until golden brown, checking after 15 minutes. It may take up to 25 minutes. 
  1. Remove cookies from baking tray immediately after baking so 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. They also freeze well.) 

Lauren Monaco Grossman

Lauren is a graphic designer and illustrator by day and home cook, baker and ice cream maker by night. She and her husband celebrate three different New Year’s holidays (four if you count Tu Bishvat) and love to host Shabbat dinners with friends and family. She enjoys expressing her multiracial identity through the food on their table and learning the stories and histories behind the recipes. She’s often making a mess in the kitchen, playing with flavors and techniques where her Peranakan and Italian ancestries are in dialogue with her Jewish identity. Visit her food blog at Mintystable.com.