Add the softened butter and powdered sugar to the bowl of a stand mixer fitted with the paddle attachment. Cream the butter and sugar until smooth and fluffy, about 2 minutes.
Add in the egg and vanilla and mix until fully incorporated.
Add in the flour, almond flour, cinnamon, and salt and mix until just combined. The dough should come together into a ball but will feel dry. If the dough doesn't come together, you can add a teaspoon of milk or water at a time until it does.
Press the dough into a disc and wrap tightly in plastic wrap. Refrigerate until firm (1-2 hours minimum but up to 24 hours).
While the dough is chilling, make the cranberry jam.
Add all of the filling ingredients to a medium saucepan. Bring to a boil over medium-high heat, stirring frequently until the cranberries begin to split open. Reduce the heat and simmer for 10-15 minutes or until the jam has thickened.
Transfer to a bowl and chill until ready to use.
Line a baking sheet with parchment paper.
On a lightly floured surface, roll out the dough ¼ inch thick and cut into snowflakes. Then cut the center out of half of the cookies. Re-roll and cutout the scraps, making sure to have an even number of tops and bottoms for the cookies.
Place cutout cookies 1-2 inches apart on your baking sheet (they won’t spread).
Place the baking sheet in the freezer for a minimum of 20 minutes (or the fridge for 40 minutes) before baking to allow the cookies to firm back up. This ensures the cookies won't spread during baking.
While the cookies are chilling, preheat your oven to 350°F.
Bake for 9-11 minutes or until the edges are set. Bake on the middle rack of the oven and rotate the pan halfway through baking for the best results.
Let the cookies cool on the baking sheet for 2-3 minutes, then remove and let them finish cooling on a cooling rack.
Let the cookies cool completely before assembling.
Once the cookies and cranberry jam are cool, spread the bottom cookies with about 1 teaspoon of cranberry jam. Sprinkle the tops cookies with powdered sugar and then place on top of the jam cookie.
Notes
The cookies themselves will last in an airtight container at room temperature for up to up to a week. However, once they've been filled with cranberry sauce and dusted with powdered sugar, the cookies will begin to soften and are best eaten within a day or two.