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Cannoli Sandwich Cookies

Happy 2023, friends! Do you have bright, colorful, nutrient-rich salads and soups on deck for January? ME TOO, and I am so excited about them. And alsoooo… I’m still baking. A lot. See, my baking tends to roll with my breaks from school, and our winter break started so late this year, just two days before Christmas, so I barely started working on holiday cookies in mid-December. I still have one whole beautiful, glorious week off of work, so I will be taking advantage of that to continue making cookies and other post-holiday sweets. I like to call this… balance.

I cannot wait to tell you about these, we’ll say, not-small Cannoli Sandwich Cookies, a long time in the making. They were borne of the failure of my longtime Purim dream: Cannoli Hamantashen. My imagination holds the most divine incarnation of cannoli hamantashen, in which the dough evokes the flavor of cannoli shells (minus the deep frying) with a touch of cocoa, cinnamon, and orange zest, and the filling is fresh ricotta, not a baked filling like normal hamantashen. I wanted to fill them *after* baking the shells, preferably made-to-order, just like their Sicilian forebears. However, this meant baking the dough triangles with nothing in the middle, which meant they would obviously collapse and not hold their triangle shapes. So I tried to shape them by carefully placing tiny wads of parchment paper in the centers and forming the triangle corners around them. In the oven they went… and out they came looking like… THIS.

I got exactly, literally, precisely… *one* triangle that didn’t collapse, fall open, or fold in on itself. I had tried this experiment a few years earlier and couldn’t remember how they came out, other than a memory that they were a lot of drama. The dough could not have been better or easier to handle, but the technique simply didn’t work. Maybe freezing them before they go in the oven could help, but since my freezer is generally a Tetris nightmare, that wasn’t happening. After that failed second batch, I thought about what else I could do with dough + ricotta + pistachios, and I decided to pivot in a new cannoli direction: sandwich cookies. Never have a cookie and a filling married more beautifully if you ask me. The cookies (using the exact same dough) are baked in flat circles a little thicker and crisper than the hamantashen so they don’t get soggy from the ricotta (with tiny chocolate chips mixed in obviously), and when you squish them together and roll them in chopped pistachios… I meeeean, if you enjoy cannoli, I really think you need to make these because the flavor tastes like biting into a Sicilian cannolo– I was actually surprised how close they came! Especially since I sadly have no plans to visit Sicily in the near future, these brought me so much joy. Furthermore, they keep in the fridge for a bunch of days, so I had almost a week of cannoli goodness.

A note about the dough: I started making Uri Scheft’s hamantashen dough from Breaking Breads a few years ago, and I pinky-swear that I will never, ever make another hamantashen dough in my entire life. IT. IS. PERFECT. Some people prefer a flakier style of dough (and I do for savory varieties), but I like mine cookie-style, and this dough is just that– tender and crumbly enough to give way when you bite it, but holds its shape beautifully in the oven when wrapped around a filling (except wads of parchment, incidentally). After making the initial plain version, I played and played until I cracked the code for how to add flavors and mix-ins, which I explored extensively in my “10 Days of Hamantashen” blog series a couple of years ago. I figured out how to swap in cocoa and add nuts, sprinkles, and pretzels into the dough successfully to create fun and creative flavors. For this dough, I wanted to emulate the flavor of cannoli shells, which have a small amount of cocoa, cinnamon, and marsala wine in them; I didn’t use the marsala, but you can easily add a teaspoon if you wish. Traditional cannoli also have candied orange peel either on top as a garnish or sometimes mixed into the ricotta. I decided to add orange zest to the dough along with a small amount of cocoa and cinnamon, which resulted in a divine cocoa-orange-almond shortbread (since the base dough calls for a little almond flour, which you cannot taste).

A few recipe tips:

  • Roll the dough thicker than hamantashen, about ¼” thick.
  • You’ll make the butter pliable not by letting it sit out to get warm, but by hulk-smashing it with a rolling pin before adding it to your mixer bowl. This keeps it cold, yet makes it easier to blend with the other dough ingredients. Also exceedingly fun.
  • Ricotta:
    • It’s important to use good-quality fresh ricotta here, something like Bellwether Farms, or even make your own, which is super easy. The grainy stuff in a tub is a different product and I would not recommend that here (or ever, actually).
    • Drain the ricotta well because you don’t want extra moisture in the filling– it should have the consistency of a firm frosting once the cookies have been filled n’ chilled.
  • These sandwiches are… hefty. I used the same 3″ cookie cutter that I use for hamantashen, so they are quite a handful. It’s up to you if you want to (gulp) share. Feel free to also use a smaller cutter, in which case you may need to pull them from the oven a minute or two sooner.

I tend to make cannoli-flavored treats around New Year’s, as I find them elegant, festive, and so decadent; maybe also I’m putting a wish into the universe to see Italy in the coming year. Even though we’re doing our dutiful post-holiday health reckoning, if you need a little sweetness in January, I cannot recommend these more. I think smaller ones (bite-sized, even) would be lovely for a party or other celebratory nibbling occasion, or if, say, you don’t think you can be trusted with the larger size. I mean, I wouldn’t know anything about that.

Cannoli Sandwich Cookies

Yields 14-16 sandwich cookies

This recipe doubles very well if you want to avoid splitting beaten eggs and want to have more cookies! I strongly recommend using weight rather than volume to measure ingredients. If you don’t plan to chill the dough overnight, make the ricotta filling first so it’s ready when you plan to bake and assemble the cookies.

For the cocoa-orange almond shortbread (adapted from Breaking Breads by Uri Scheft):

  • 390 grams (3¼ cups) all-purpose flour
  • 50 (½ cup) grams blanched almond flour
  • 2 tablespoons Dutch-processed cocoa powder (such as Valrhona), sifted
  • 1 teaspoon fine sea salt
  • ¼ teaspoon ground cinnamon
  • 225 grams (2 sticks/1 cup/8 ounces) cold unsalted butter
  • 100 grams (scant 1 cup) confectioners’ sugar
  • 50 grams (¼ cup) granulated sugar
  • Zest of ½ medium orange
  • 1½ large eggs, beaten, at room temperature

For the ricotta-chocolate chip filling:

  • 400g (1¾ cups) fresh ricotta, drained well for at least 4 hours or overnight, as needed to remove moisture
  • 90g (scant ½ cup) granulated sugar
  • ½ teaspoon pure vanilla extract
  • 55g (⅓ cup) micro or mini chocolate chips, or finely chopped chocolate

For assembly:

  • 35g (⅓ cup) chopped bright green pistachios
  • Confectioners’ sugar for dusting

To make the almond shortbread dough:
Line a rimmed quarter- or half-sheet pan with a piece of parchment paper and set aside.

Whisk together the all-purpose flour, almond flour, cocoa powder, salt, and cinnamon in a bowl; keep it nearby.

Lay a piece of parchment paper on your work surface and place 1 stick of butter on top. Smash the butter with a rolling pin several times to soften/flatten it, then transfer it to the bowl of a stand mixer fitted with the paddle attachment. Repeat with the remaining stick of butter.

Add the confectioners’ sugar, granulated sugar, and orange zest to the bowl. Mix on low just until the loose sugar is incorporated. Scrape down the bowl and the beater, and mix again for about 30 seconds on medium-low speed, making sure that the zest is evenly distributed and not clumped together. You want the butter to still be cold, and you’re mixing minimally here to avoid aerating the butter.

Pour in the beaten eggs and paddle on low speed until the mixture looks like wet scrambled eggs– the butter chunks should all be coated in egg liberally.

Add the dry ingredients to the bowl (gradually if making a double batch) and mix on low speed until most of the flour has been incorporated; it’s helpful to stop and scrape down the bowl and beater midway through.

Turn the dough out onto a clean work surface and finish bringing it together by hand or with a flexible bench scraper. Roll it out to about ½” thick and transfer it to the prepared sheet pan. (It will not fill the pan.) Cover the pan tightly with a piece of plastic wrap and chill in the refrigerator for at least 2 hours (or until firm), or up to 2 days.

To make the filling:
Place the ricotta in a bowl and mash it lightly with a fork to loosen it a bit. Whisk in the sugar and vanilla, then stir in the small chocolate chips. Cover the bowl tightly with plastic wrap and chill for 8 hours or overnight.

To bake & assemble the sandwich cookies:
When you’re ready to roll and cut the dough, preheat the oven to 350°F and place a rack in the center position. Line 2-3 rimless cookie sheets with parchment paper. Remove the dough from the fridge and let it soften for 5-10 minutes.

On a lightly floured work surface, roll the dough out to a thickness of ¼”, flouring and moving the dough around as needed to avoid sticking to the work surface and rolling pin. Feel free to cut off pieces of dough with a sharp knife or bench scraper and work in smaller batches as needed.

Cut out circles with a 3″ round cutter and transfer them to one of the prepared cookie sheets spaced about 2″ apart. Try to cut them out as closely as possible to avoid having a lot of scraps. Re-roll the scraps and repeat until you’ve filled the cookie sheet. Transfer the pan to the fridge for 15 minutes (or the freezer for 5 minutes) to chill the dough circles.

Bake the cookies for about 14-18 minutes, rotating the pan halfway through baking. They should be firm, but they should not get very brown in the oven. Set the pan on a wire cooling rack to cool completely. Repeat with the remaining dough and baking sheets; you should have approximately 30-32 cookies.

Prepare a large clean work surface. Line a rimmed sheet pan with parchment paper and set it near the work area. Transfer the ricotta mixture to a pastry bag fitted with a medium cake tip of your choice. (You could also use a spring-loaded ice cream scoop or two spoons.) Pour the chopped pistachios onto a plate.

Pair up the cookies and turn over one cookie from each pair. Starting in the center of each upside-down cookie, pipe a tight spiral or mound of ricotta all the way to the outer edge. Top with the second cookie and gently press them together to squeeze the filling slightly beyond the cookie edge (so it can catch onto the chopped nuts). Roll the cookie sandwich gently in the pistachios so that they stick to the filling all the way around. Place the cookie on the prepared sheet pan and repeat with the remaining cookies and filling.

Cover the pan tightly with plastic wrap and transfer it to the fridge. Let the assembled sandwich cookies chill and set for at least 30 minutes before eating. Lightly dust them with confectioners’ sugar and serve.

Store the cookies in an airtight container in the fridge for up to 5 days or so– they will get even better as they set for a day.

© Dafna Adler & Stellina Sweets, 2023.

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© Dafna Adler & Stellina Sweets, 2023. Unauthorized use and/or duplication of this material without express and written permission from this blog’s author/owner is strictly prohibited. This includes recipes, photos, and all other original content. Excerpts and links may be used, provided that full and clear credit is given to Dafna Adler and Stellina Sweets with appropriate and specific direction to the original content.

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