I always loved rugelach cookies growing up.  And I still like them - although I only get to eat them when I make them these days.  I'll happily eat any flavor - a nice tart jam works well, but my favorite has always been chocolate rugelach.  I've made these chocolate rugelach many times now, and I love the flakiness of the dough combined with the chocolate filling.  They use a dough similar to the jam-filled hamentashen recipe. Yum! If you want extra chocolatey-filled rugelach, you can double the filling amount, but I find these were messier to work with, and I liked the balance of filling to dough that I've put here.  Enjoy!  

Fresh baked chocolate rugelach, ready for taste-testing!

Rugelach with added chopped chocolate to the filling. 

Chocolate Rugelach!

Preheat oven to 375 F (or wait and do this later if you're going to chill your dough).  Line 1-2 baking pans with parchment paper.

Chocolate Filling:

Melt together in a bowl:
3.5 oz semi-sweet or dark chocolate chips

1 Tbsp butter

Add and mix in thoroughly: 

scant 1/4 cup sugar

1/8 - 1/4 tsp salt

Optional - dice 1/2 cup chocolate chips to sprinkle on top of the chocolate spread

Set aside filling and prepare the dough.  

Dough:

Beat until light and fluffy:
1/2 cup butter, softened
3 oz cream cheese, softened
3 Tbsp sugar

Add and beat in until smooth:
1 egg
1 tsp vanilla extract
zest of 1 lemon

Mix in a small bowl  before adding to wet ingredients:
1 1/2 cup Kristin's Gluten-Free Flour Mix
1/2 tsp xanthan gum
1/4 tsp salt

Mix dough together until smooth.   Most recipes recommend chilling, but I find because I am making these rolled between plastic wrap, I can just make them right away without any refrigeration.   Roll out the dough between plastic wrap to make a rectangle about 8" x 30".  

Spread the chocolate filling from above evenly over the dough.  Sprinkle extra diced chocolate chips if using on top of the chocolate spread.  Have a small bowl of water available to use to help with any stickiness while you're rolling and slicing your dough.  Use the plastic wrap and wet fingers, as needed, to tightly roll up the dough so you have a long, 30" log. 

A log of dough - ideally roll it a bit tighter than this version - it ended up being a little lopsided.

You have THREE options at this point.  You can chill the log of dough for 60-90 minutes before slicing (this does make for neater cuts, but I tend to go for speed), or you can slice the dough and chill them for 20-30 minutes on the baking pan before baking.   If you're short on time, you can just bake them right away, but you'll end up with neater rugelach cookies if you can chill them for the 20-30 minutes before baking. 

Use a sharp knife that you clean between each slice, slice the rugalach into 1" pieces and place them on the parchment-lined pan.  These don't spread much, so you can fit quite a lot on one pan.  

Just before baking, brush the tops of the rugelach with: 

1 egg, beaten

And sprinkle with: 

cinnamon-sugar (1/2 cup white sugar + 1-2 Tbsp cinnamon mixed together is a nice ratio)

Mmm.. pretty chocolate rugelach, ready to bake.

Bake trays of rugelach at 375 F for about 20-23 minutes, until a nice golden brown.  Let cool on the pans ~5 minutes before removing to wire racks to fully cool.  Enjoy!!! 

Fresh from the oven - a nice golden brown chocolate rugelach cookie.

Chocolate Rugelach Recipe by Successfully Gluten Free!