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150426_Rugelach-29This is a thorough and overly personal explanation of one of my favorite things to bake: rugelach. Rugelach are an Ashkenazi Jewish pastry consisting of dough rolled around a filling, usually in a crescent shape. The chocolate filling in this recipe creates moisture and density, and the dough is light but flavorful.

All rugelach are kind of mediocre except for these. These are exceptional.

Rugelach also conveniently merge my major interests: baking, obsessive TV-watching, and Jewish culture. This recipe is built off one I originally got from my late Great Aunt Rhoda. My mom found it in an old synagogue women’s group cookbook, sandwiched between four other rugelach recipes that I would never bake again. I didn’t know my great aunt very well, but my mom makes sure I take a moment of silence in her memory whenever I bake these. So, thank you, Great Aunt Rhoda and Mom.

There are only three ingredients in this dough, so you won’t have a ton of time to watch TV while you make it, but you’ll be able to watch at least 30-40 minutes of TV while you create the cookies themselves!

Ingredients List

Dough:
1 cup unsalted butter (softened)
8 ounces cream cheese (softened)
2 cups flour

Filling:
1 cup chocolate chips
2 teaspoons Cinnamon
1 cup Sugar
(adjust to taste, amounts can be approximate)

Materials:
Additional cinnamon and sugar for rolling out dough
baking sheets
parchment paper
rolling pin or wine bottle

Making the Dough

Mix together the softened cream cheese, butter, and flour. I used my mom’s stand mixer, but if everything is at room temperature it shouldn’t be too hard to do it with a hand mixer or wooden spoon. When the dough is completely mixed, light, and cohesive, it’s done.

Divide up the dough. I usually divide it into three sections, according to the recipe I use, but it just depends on how large you want the rugelach. The larger the section, the larger the rugelach, obviously, and I prefer tiny rugelach. Wrap each section in plastic cling film and flatten into a disc. Put them all in the fridge in a little stack or side by side.

The longest amount of time I’ve ever let the dough chill in the fridge is three days, and the shortest is two hours. Everything comes out exactly the same.

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Creating the Cookies

Preheat the oven(s) to 350 degrees right when you’re ready to start rolling these out.

Make the filling. For the chocolate-filled ones like I made here, get chocolate chips or some chocolate bars or something. My family has a giant tub of chocolate chips in the cabinet that someone put a spoon in three years ago and we all eat from constantly and don’t even think it’s weird. I used those.

150426_Rugelach-13Using either a mixer, blender, or knife and cutting board, chop the chocolate into very fine crumb-like pieces. Try to keep them on the smaller side. Mix in a larger bowl with cinnamon and sugar.

I recommend you put aluminum foil down all over your work surface to make cleaning easier. I would roll out the dough on a large cutting board, since you’ll be slicing into the dough eventually.

Put on Netflix or Hulu or a YouTube playlist, because your hands are going to get disgusting and you NEED continuous play to distract yourself. I recommend watching something you don’t find stressful or potentially secondhand embarrassing, because skipping through when your hands are gross is a disaster. Perhaps a video playlist of Alexa Chung putting on her own eyeliner or the Fast and Furious movie of your choice?

Take out your baking sheets and line them with parchment paper.

Sprinkle the mixture of cinnamon sugar on the cutting board to make rolling the dough easier. This also gives the previously plain dough some flavor.

Take the first disk of dough. Sprinkle the cinnamon sugar mixture over the rolling pin/ bottle of wine. The dough will be difficult to roll out at first, and if, like me, you have improbably little arm strength, you should really throw your body weight into it. Re-sugar the cutting board and the rolling pin. It gets easier as you roll the dough out more, lose patience, and gain aggression.

150426_Rugelach-18You may have to roll this out a few times, folding it back together and rolling it out again. Try to get it into as much of a circle as you can. I sometimes use a pizza cutter to get edges or weird sides out so I’m not constantly re-rolling the dough. It is typically at this point that I become frustrated and start questioning how much I even want rugelach in the first place. You’ve come this far, though, and in my case my mom probably requested that I make them for Chanukkah/Rosh Hashanah/a general family gathering, and everyone will be extremely annoying if I don’t come through.

Using a pizza cutter, cut the circle into 16 triangles. First slice through the center to make two halves, then slice into quarters, and so on and so forth.

Sprinkle the filling over it. Try to get the larger chunks of chocolate around the outer edge of the circle, so they will stay in the middle of the rugelach. Don’t worry about overfilling the rugelach, since excess filling will fall out during the rolling process.

150426_Rugelach-21Starting from the outside, roll a triangle towards the circle’s center, trying to keep as much of the filling in as possible. A lot will spill out, which is OKAY and expected — you’ve accounted for this!

Make the edge of the tip the bottom of the rugelach, and fold the edges so it is a little like a crescent. Do this for every tiny triangle. As you create each rugelach cookie, place it onto your baking sheet. They don’t expand, so you can fit all 16 on a regular baking sheet. The parchment paper is there so you don’t have to worry about them sticking.

Bake for about 15 minutes, but definitely check between minutes 10-15 to see how they are doing. They should be a little bit browned and puffed up, but not too much. Light and crispy on the outside, dense on the inside.

Take them out of the oven when they’re done and put the baking sheet on a surface that can handle a hot baking sheet, like your stove or something. After a few minutes, you can transfer them to a wire rack or cooling sheet and then shove them all directly into your mouth or wait a bit and create a little rugelach hoard.

Repeat for the other two disks.

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Great Job!

Whenever I make these I feel as though I really have a shot at opening a wildly successful Jewish bakery, or medium-successful Jewish food truck. I would make rugelach, my mom would make several types of kugel, and it would be adorable.

You can give these out to any coworkers you like or need to impress, but be prepared to explain what rugelach are 30 times, until you just start telling them you brought in a Jewish pastry (same explanation works with Hamantaschen, Babka, mandelbrot, etc).

Also, bring them to your grandparents! They’ll be so proud and glad that you visited.

If you make these, I hope they come out well. Please let me know in the comments if you have any issues or questions!

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All photos by Jackie Friedman.

Lisa Yelsey is a young, beautiful associate editor from New York. She is passionate about baking, writing, and every TV show.

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