Rosh Hashanah - Chocolate Cherry Rugelach (finally!)

So this recipe was attempted for the first time last year for Yom Kippur which was my first High Holiday ever (Izzy's Mama was a big help by giving me all her tried and true as my welcome to Jewish holidays). Unfortunately they didn't really come out as I expected. They ended up being a bit messy - some unrolled, some burned, some overstuffed and dripping carmelized jam - not terrible tasting but certainly not pretty. So this year I was determined to get them done right. However that is easier said than done and to be honest out of the 6 trays I made (3 recipes) I am really only 50/50 which isn't good odds. All of my Jewish friends said that rugelach is something that is best bought and not attempted at home but if you know anything about me that just makes me want to make them even more!
...before
My major issue seemed to be that I was overstuffing these and not really cutting them correctly which lead to the little rolls busting open and spilling all the jammy goodness all over (which then burns). My first batch came out similar to last year and so I had to try for another shot at these later in the week.
...after
I ended up finally getting this right on thursday after switching up my jams (try to find one without any chunks of fruit), lowering my oven temp (350 F) and shortening the cooking time (30 min). These cookies are definitely best when they are just barely browned off so don't cook them too long or else they get crunchy instead of light and flakey.

I also ended up rolling the dough into 2 large rectangles instead of a round and making large triangle shapes (similar to what pre-made cresent rolls in the can look like). I also placed just a few dried cherries and chocolate chips on the wide side of each so that I was able to roll them easily.

original recipe from: http://www.izzyeats.com/2007/09/must-stop-eating-these.html

Dough
2 cups all purpose flour
2 tablespoons sugar
1/4 teaspoon salt
1 cup (2 sticks) chilled unsalted butter, cut into 1/2-inch pieces
6 ounces chilled cream cheese, cut into 1/2-inch pieces

Filling
1/2 cup sugar
1 teaspoon ground cinnamon
12 tablespoons cherry preserves (Polaner all fruit works well)
8 tablespoons dried tart cherries
8 tablespoons miniature semisweet chocolate chips
1/2 c powdered sugar
1/3 cup (about) whipping cream


1) Preparation for dough by all ingredients to mixer (I used a kitchen aid with the paddle, hand mixers are too weak but the original recommends a food processor but unfortunately I don't have one....yet!) and blend together until it begins to clump together.
2) Gather dough into ball.
3) Divide dough into 2 and roll out each between wax paper into a large rectangle about 1/8 to 1/4" thick and refridgerate 30 min or more
4) Line large baking sheet with parchment paper.
5) Mix sugar and cinnamon in small bowl.
6) Take the dough from the fridge, peel off the wax paper and dust with powdered sugar if it is sticky.
7) Spread 3 tablespoons cherry preserves over dough, leaving 1-inch border and sprinkle it with 2 tablespoons cinnamon sugar.
8) Trim into triangles and place a few chocolate chips and cherries on the wide edge.
9) Starting at wide end of each wedge, roll up tightly.
10) Arrange cookies on prepared baking sheet, spacing 1 1/2 inches apart
11) Place baking sheet in freezer 30 minutes.
12) Position rack in center of oven and preheat to 350°F.
13) Brush cookies lightly with whipping cream. Bake frozen cookies until lightly browned, about 30 minutes.