In a stand mixer fitted with a hook attachment, add the flour, yeast, sugar, and salt. Mix to combine. You can also knead the dough by hand or use a hand mixer with hook attachments.

Then, add the milk and eggs. Knead on medium speed for 5 minutes or until homogeneous in consistency.

Add the butter in 4 parts and knead each part until it’s completely incorporated (the dough can look like it’s disintegrating but will come back together eventually). When done, knead the dough for 7-10 minutes on medium until it pulls away from the sides of the bowl, and you can stretch a small piece of it into a square, creating a film thin enough for light to pass through (windowpane test). The dough should be very soft, smooth, and not sticky.

Cover the bowl with plastic wrap and leave it at room temperature to proof for 1 to 2 hours, depending on how warm it is in your kitchen until it doubles in volume.

In a microwave-safe bowl, add all filling ingredients and heat in the microwave in short increments, mixing in between until the chocolate has melted. Set aside to cool down for 10 minutes.

Shaping and baking rugelach

Punch down the dough and place it on a floured surface. Dust with flour on top of the dough.

Roll out the dough into an 18” x 22” (45cm x 55cm) rectangle.

Spread the filling on top, leaving thin borders untouched.

Take one of the short sides of the rectangle and fold the dough slab in half.

Roll the slab with the filling inside as thin as you can so you can see the filling through the dough. Keep the shape of your slab rectangular.

Trim the edges using a long sharp knife or a pizza cutter. Then, cut the slab into 28 triangles. You can adjust the amount of rugelach you make by cutting out larger or smaller triangles.

Take one triangle and gently elongate it by tugging its long, pointy tail. Then tug the short tails of the triangle outwards a bit and roll it from the short side of the triangle towards the tail. The crescent should be rolled tight but not to the point that the layers are squeezed.

Place the crescent on baking sheets lined with parchment paper so the pointy tail is precisely under the crescent body. Gently press on top of the crescent to secure the position. Repeat with the rest of the triangles.

Cover the crescents with plastic wrap and place them in a warm, draft-free space to proof for 30-60 min or until they are puffed up.

Preheat the oven to 350F (175C).

Brush the crescents with egg wash and bake one tray at a time in the middle of the oven for 20 – 25 minutes or until deep golden brown.

In a saucepan, add all sugar syrup ingredients.

Heat over medium heat until the sugar has dissolved and the mixture simmers.

Pour into a bowl to cool down a bit.

Brush freshly baked rugelach with warm syrup and serve!