Preheat oven to 350F. Line a cookie sheet with parchment and set aside.
Process all vanilla layer ingredients in a food processor until the mixture begins to form a ball (note if the mixture is too sticky, add a bit more flour, if too dry, add a bit more maple syrup). Form the mixture into a ball with your hands and knead briefly, then flatten into a disk. Place the disk between two sheets of parchment paper on a flat surface and use a rolling pin to roll out into an ⅛" thickness, and roughly the shape of a rectangle. Remove the top layer of parchment and set aside (leaving the base resting on the bottom parchment sheet for now).
Process all chocolate layer ingredients in a food processor until the mixture begins to form a ball (note if the mixture is too sticky, add a bit more flour, if too dry, add a bit more maple syrup). Form the mixture into a ball with your hands and knead briefly, then flatten into a disk. Place the disk between two sheets of parchment paper on a flat surface and use a rolling pin to roll out into an ⅛" thickness, roughly into the same shape and size rectangle as the vanilla layer. Peel off the parchment layer from the top.
Carefully flip the chocolate layer over the vanilla layer, leave the parchment paper on top and go over the now combined layers with a rolling pin to flatten them a little. Remove the sheet of parchment from the top. Starting at on long edge of the rectangle, carefully roll up the two layers into a log (I use the bottom sheet of parchment paper to help by lifting one of the sides of the rolled out dough and rolling it up from there). *Note if you want your cookies really round, freeze the log for 20 mins, then roll back and forth on the counter to get it into a round shape. If you don't mind them being a bit more flat (as pictured) skip the freezing stage.
Remove the parchment from the roll (ok to leave it resting on top), and slice the roll into rings that are approx. a ¼" thick. Transfer each cookie onto prepared cookie sheet.
Bake in a pre-heated oven for 10 mins (or bake longer for crispier cookies to your liking). Remove from oven and allow the cookies to cool a few minutes (they will firm up a bit as they cool off). Enjoy!