The Bojon Gourmet

Make the jam (skip if using storebought jam):
2 In a small, heavy-bottomed saucapan, combine the cranberries, sugar, vanilla pod and scrapings, and port. Bring to a boil over medium heat, then simmer over low heat until thick and chunky, 10-15 minutes, stirring frequently to prevent burning. Let the jam cool completely.
Meanwhile, make the dough:
5 In the bowl of a food processor, pulse together the rice, millet, and oat flours with the cornstarch, sugar, xanthan gum, and salt to combine. Scatter over the butter and cream cheese pieces, and process until the dough comes together in large clumps, 15-30 seconds.
6 Dump the dough onto a piece of parchment paper and gather it into a rough log. (No need to wash the bowl just yet.) Place another piece of parchment on top of the dough, and use a rolling pin to roll the dough into a long, skinny rectangle that measures 16 x 8 inches (40 x 20 cm) and is 1/8-inch thick (1/3 cm). With every few strokes of the pin, peel back the top piece of parchment, place it back on the dough, flip the dough and papers upside-down, peel back the new top piece of paper, place it back on the dough, and proceed. If the dough sticks to the paper, dust it lightly with millet flour. If your rectangle is more oval, you can trim the uneven ends, stick them onto the corners, and continue rolling in order to form an even rectangle.
7 When the dough is rolled out, trim all the edges flat and straight. Reserve the dough at cool room temperature while you prepare the fillings. (The dough becomes brittle when chilled; but if it's warm in your kitchen and the dough becomes sticky or melty at any point, stick it in the fridge to cool it off a bit.)
Prepare the fillings:
10 Pulse the toasted and cooled walnuts in the food processor until finely chopped (but don't let them become nut butter). Dump the walnuts into a bowl and wipe out the food processor. Remove the vanilla pod from the cooled cranberry goop, and add the goop to the food processor. Puree smooth; you should have about 3/4 cup. In a tiny bowl, stir together the 1 tablespoon sugar and the cinnamon. Set aside.
Assemble the rugelach:
13 Slide the rolled-out dough, still on its parchment, onto a rimless cookie sheet for easy maneuvering. Thinly spread the cranberry jam over the dough leaving a 1/2-inch (1.25 cm) border on both long sides (a small, offset spatula works well for this). Sprinkle the chocolate evenly over the jam, and sprinkle the ground walnuts over the chocolate. Use your palms to pat everything down; the nuts and chocolate will adhere to the jam, making the rugelach easier to roll.
14 Lift up a long edge of parchment and use it to begin to rolling up the rugelach as tightly as possible. It's ok if the dough cracks a little; it will sort itself out as it bakes. When the rugelach log is rolled (which I now dub the "rugeh-log"), leave it seam-side down. Cover it with parchment and give it a gentle squeeze, as though you were rolling sushi. Transfer the rugeh-log, still on its pan, to the freezer and leave there until firm, at least 30 minutes. (At this point, you could wrap and freeze the log until ready to bake.)
Bake the rugelach:
17 Position a rack in the upper third of the oven and preheat to 375ºF (190ºC). Line a baking sheet with parchment paper.
18 Remove the frozen rugeh-log, unwrap, and place it on a cutting board. Brush it all over with the heavy cream, and sprinkle with the cinnamon sugar. Slice the rugelach into scant 1-inch thick pieces (2 cm). Too thin, and the rugelach will flop over as they bake, so use a ruler to be safe. Place the rugelach seam-side down on the lined baking sheet and bake until golden on top and cooked through, 25-30 minutes. Immediately use a spatula to remove the rugelach from the baking sheet and onto a cooling rack. Let cool at least 10 minutes.
19 Store the rugelach airtight at room temperature for up to 1 week.