Step 1 of 18
Chocolate-Orange Rugelach
Place the flour, granulated sugar, and salt in the bowl of a food processor. Pulse 2-3 times to combine.
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Step 2 of 18
Chocolate-Orange Rugelach
Cut the butter and cream cheese into 3/4-inch pieces. Add to the food processor and pulse just until the fats reach the size of beans.
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Step 3 of 18
Chocolate-Orange Rugelach
Add the sour cream to the food processor. Pulse a few more times, just until the dough begins to hold together.
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Step 4 of 18
Chocolate-Orange Rugelach
Turn the dough onto a lightly floured work surface. Divide into three equal portions, gently shaping each into a disk approximately 1-inch thick. Wrap disks in plastic wrap and refrigerate until somewhat firm but still pliable, 30 minutes to 1 hour.
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Step 5 of 18
Chocolate-Orange Rugelach
Preheat the oven to 350°F.
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Step 6 of 18
Chocolate-Orange Rugelach
Line two baking sheets with parchment paper. Set aside.
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Step 7 of 18
Chocolate-Orange Rugelach
Finely grate the zest from the orange.
PRO TIP Not a fan of orange? Leave out the orange zest for a delicious chocolate rugelach.
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Step 8 of 18
Chocolate-Orange Rugelach
Place the brown sugar, cocoa powder, cinnamon, orange zest, and salt in a large mixing bowl and mix to combine. Stir in the chocolate chips.
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Step 9 of 18
Chocolate-Orange Rugelach
Remove one disc of dough from the refrigerator. Unwrap and place on a well-floured work surface. Gently roll dough into a 1/4-inch-thick circle. Spread one portion of the apricot preserves evenly over the surface of the dough (enough to lightly cover). Sprinkle one third of the filling mixture over the preserves, and lightly press down to help it stick.
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Step 10 of 18
Chocolate-Orange Rugelach
Use either a pizza wheel or sharp knife to cut the circle into eight equal wedges (like a pizza).
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Step 11 of 18
Chocolate-Orange Rugelach
To form cookies, begin from the wide end of a wedge. Carefully roll dough towards the pointed tip, finishing with the tip pointed downward and slightly tucked under. Turn each end of the rolled cookie inward toward the tip. The final shape of the cookie should resemble a croissant. Don't worry if some of the filling escapes.
PRO TIP If some of the filling and chocolate chips escape during rolling, you can stuff a little back inside the openings in the pointed ends before shaping them inward.
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Step 12 of 18
Chocolate-Orange Rugelach
Repeat with the remaining dough and filling until all the cookies are shaped. Arrange 12 cookies on each baking sheet.
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Step 13 of 18
Chocolate-Orange Rugelach
Whisk the egg in a small mixing bowl until blended. Using a pastry brush, lightly brush tops of cookies with the beaten egg.
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Step 14 of 18
Chocolate-Orange Rugelach
Bake the cookies on upper-third and lower-third racks of oven for 10 minutes.
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Step 15 of 18
Chocolate-Orange Rugelach
Switch the rack position of the baking sheets. Continue baking until cookies are deeply golden brown on top, and bottoms appear crisp and golden brown, 15-20 minutes.
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Step 16 of 18
Chocolate-Orange Rugelach
Check to see that cookies are done. Remove from oven or add time as needed.
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Step 17 of 18
Chocolate-Orange Rugelach
Let cookies cool on the baking sheets for 5 minutes, then transfer to cooling racks to cool completely.
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Step 18 of 18
Chocolate-Orange Rugelach
Shortly before serving, dust the cookies liberally with powdered sugar. The cookies are at their most buttery and crisp if made and served on the same day, but can be kept for up to two days in an airtight container at room temperature.