Chocolate Rugelach (Gluten Free + Refined Sugar Free)

These Chocolate Rugelach are incredibly tender and flaky, thanks to the cream cheese-based dough. These refined sugar-free and gluten-free rugelach are filled with dark chocolate shavings for an irresistible holiday treat.

For as long as I can remember, I’ve wanted a garden. Mostly because I found the idea of growing my own food to be a novel one, having grown up in suburban San Diego with not many gardens around that I remember, save for the garden in our school yard.

As soon as I got my first apartment out of college last year, I recruited my roommate Ally to help me assemble an herb garden. We loved and tended to it all summer and into fall, watching it thrive and using the fruits of our labor in our meals and letting them inspire my treats, like these Raspberry Mint Brownies. Then, Seattle winter came and our plants all died a sad death, turning into shriveled gray twigs.

Now that I’m pretty much settled into my new apartment in San Diego, I decided it was time for as much of a garden as I could squeeze onto my relatively small patio. I started with herbs – I have basil, mint, thyme, rosemary, and the most recent addition, peppermint.

My most exciting recent addition, though? My citrus trees!!! I took forever at the nursery as I decided precisely which trees I wanted, and after consulting with my Instagram followers and the kind man at the nursery on which to choose, I went with a Meyer lemon tree, a drawf Bearss lime tree, and a dwarf Rio Grande grapefruit tree.

I finally got it all on my patio and just seeing them out there gives me warm fuzzies inside – I want to add even more goodies out there too! Let me know your favorite foods you can grow in a container in the comments if you grow anything :D it’s addicting to be able to snag ingredients from a few feet outside my kitchen, and I’m already antsy for my trees to be heavy with fruit.

The part of me that wants to grow my own food is the same part of me that loves to bake and cook – there’s a satisfaction in the process of creation, whether it’s food, art, or fruits and veggies.

These Chocolate Rugelach? They’re definitely a creation worth making. They aren’t the quickest cookies to make, as they do have a few steps, but they aren’t hard to make at all and the outcome is incredibly delicious.

I’ve made rugelach a few times before (see Chocolate Chip Rugelach, Nutella Raspberry Rugelach and Apple Butter Rugelach) and each time, I have a hard time not devouring the whole batch straight off the pan. This year, I vowed to make a gluten-free and refined sugar-free version.

It required a few tests to get the ratios right and make sure they didn’t end up so buttery that they they lost their structural integrity, but my family definitely didn’t mind devouring the test batches. These rugelach, which are a traditional Jewish cookie, are incredibly tender and flaky thanks to the signature cream cheese dough.

The cream cheese lends a softness and a tang to the dough, and the butter makes the cookies bake up to be super flaky. There’s only a small amount of sugar in it, letting most of the sweetness come from the filling. I like to add a hint of cinnamon for warmth, too.

I filled these gluten-free rugelach with very finely chopped dark chocolate, but you can go wild with different fillings. In my test batches, I made some with apple butter, some slathered with almond butter and sprinkled with chocolate, and some with strawberry jam + chopped walnuts. You can also go more traditional, with raisins and walnuts.

I baked up a whole batch, and have been eating them all the time out of the freezer – they’re irresistible! You’re going to love these gluten-free chocolate rugelach – I bet you won’t be able to eat just one of these irresistibly flaky cookies.

This recipe is also a part of a super fun virtual cookie swap #calmandbrightcookienight with 33 (!!!) delicious cookies by some super talented bloggers. The swap is being hosted by The Modern Proper – head over to their post to see ALL the cookies!

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Remember to #bakerita if you try the recipe!

Chocolate Rugelach (Gluten Free + Refined Sugar Free)

Save Print Prep time 3 hours Cook time 25 mins Total time 3 hours 25 mins Author: Rachel Conners Serves: 48 cookies Ingredients

1½ cups (144) almond flour
½ cups (56g) tapioca flour
3 tablespoons coconut sugar
¼ teaspoon salt
½ teaspoon cinnamon
¾ cup unsalted butter, slightly softened, cut into small pieces
1 (8 ounce) package cream cheese, slightly softened, cut into small pieces

For the filling

8 oz. dark chocolate, chopped very finely
Milk, to brush on top of cookies

Directions

In a the bowl of a stand mixer, combine the almond flour, tapioca flour, coconut sugar, salt, and cinnamon on low until mixed.
Add in the butter and cream cheese and mix on low speed. The dough will get crumbly and then start to come together. Mix until the dough is just combined - some small bits of butter are okay. This can also be done in a bowl with a pastry cutter and wooden spoon, if you don’t have a stand mixer.
Shape the mixture into a large rectangle. Wrap the dough in plastic wrap and chill for at least 2 hours or up to 1 week.
When ready to prepare the cookies, preheat the oven to 350°F.
Cut dough into 4 equally-sized pieces. Sprinkle your rolling surface with tapioca flour (or in between sheets of parchment paper) and roll out one piece of dough at a time into a 12-inch by 4-inch rectangle. Sprinkle ¼ of the finely chopped chocolate evenly on the dough and lightly run your rolling pin over the chocolate to press it into dough.
Working from the long end, gently roll the dough into a 12-inch long log. You can use a bench scraper to help you lift and roll the dough more easily. Once it's all rolled up, make sure the seam is at the bottom. Place in the freezer for 15 minutes to firm up the dough (this will also help you make cleaner cuts. You can also wrap the dough plastic wrap and freeze for up to 3 months at this point).
Remove from the freezer. Brush the dough log with milk. Cut each log into 12 equal pieces, about 1” each. Place upright on lined baking sheets.
Bake each sheet individually for 22-25 minutes or until lightly golden. Cool on wire racks. Store in airtight containers - they also freeze really well.

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