Step 1

Place the flour, sugar and salt in the food processor and process for about 10 seconds to combine. Cut the cream cheese and butter into chunks and add them to the food processor. Pulse until the dough resembles small pebbles, about 25-35 pulses.

Step 2

Pour the mixture onto a work surface and press it into a 6 x 8-inch rectangle. The dough will still be crumbly at this point but should have a marbled appearance with small visible pieces of cream cheese and butter.

Step 3

Fold the dough into a letter fold. To create the letter fold, pick up one of the short ends (the 6-inch end) of the dough (on the right or the left) and fold it a third of the way over the rest of the dough. Repeat with the other end. Turn the long side towards you and roll it into a 6 x 8-inch rectangle. The dough will still be crumbly after the first fold.

Step 4

Repeat the folding step three more times. Each time pick up pieces of dough that have fallen to the side and press them into the top of the dough. Lightly flour the work surface throughout the folding and rolling to keep it from sticking to the work surface. The last time the dough should come together and be pliable.

Step 5

Divide the dough into 4 pieces, about 188 grams each. Shape each piece into a rectangle shape and wrap it in plastic wrap. Refrigerate for at least 1 hour, but no longer than 2 days. The dough can be frozen for about 1 month. If freezing for more than a day, place the plastic-wrapped dough in freezer bags.

Step 6

Finely chop the chocolate. The pieces should be no bigger than 1/8-inch in size. Place the chocolate, brown sugar, granulated sugar, cocoa, and ground cinnamon in a medium bowl and whisk to combine.

Step 7

Line a rimmed baking sheet or flat plate with parchment paper. Melt the butter and let it cool until it is just barely warm.

Step 8

Place the dough on a work surface and let it sit for about 10 minutes. Flour the work surface and roll it out to a 14 x 5-inch rectangle. Brush the dough with the melted butter.

Step 9

Spread 4-5 tablespoons of the chocolate filling on the dough and leave about a 1/4-inch border all the way around. Lightly press the chocolate filling into the dough.

Step 10

Starting at the long edge roll the dough into a tight spiral. When it’s rolled up, place the seam-side down and press it into the surface. Trim the edges so the log is 12-inches long. Cut the log into 8 pieces, 1-1/2 inches long each.

Step 11

Place the unbaked rugelach on a tray and refrigerate them for at least one hour.

Step 12

At this point, the rugelach can also be frozen and baked directly from the freezer. Place the rugelach in a single layer on a baking sheet or board, Freeze them, then place them in a freezer bag. When ready to bake, remove them from the freezer, brush them with the egg wash, sprinkle with the sugar and bake until golden brown.

Step 13

Preheat oven to 375 degrees.

Step 14

Place the rolled up rugelach on a rimmed baking sheet 2-inches apart. Brush with the egg-milk mixture and sprinkle with the demerara sguar. Place in the oven and bake for 16-18 minutes until golden brown. Remove from the oven. Allow to cool on the baking sheet for about 5 minutes before moving to a cooling rack.

Step 15

The cookies are good at room temperature in an airtight container for ten days.