Cranberry Pinwheel Cookies

Make the Cranberry Filling
1 In a nonstick skillet over medium heat, add the honey, brown sugar, apple cider vinegar and the orange juice.
2 When the wet ingredients have combined, add the cranberries, ginger and salt.
3 Cook over medium heat until the cranberries begin popping and breaking down (about 5-10 minutes.)
4 Remove from the heat, and let cool for 5 minutes.
5 Pour the cranberry filling into the base of a food processor. Add the pecan pieces.
6 Pulse the cranberries in the food processor until they have broken down. Continue pulsing until the cranberries reach the desired consistency.
7 When the cranberry filling is a spreadable consistency, with no large chunks of cranberries or pecans, remove from the food processor. Transfer into a bowl, and cover with plastic wrap.
8 Place in the refrigerator, and let chill and set up for at least one hour.
Make the cookie dough
1 In a large bowl, combine the flour, baking powder, baking soda, salt and cinnamon. Whisk together. Set aside.
2 In another large bowl, combine the unsalted butter and sugar. Using a hand-held mixer (or a stand mixer), cream the butter and sugar together until light and fluffy.
3 Measure in the vanilla and egg to the butter/sugar mixture. Using the hand-held mixer, whip them together until smooth.
4 Add the milk and vinegar. Beat those into the wet ingredients until smooth.
5 Carefully measure the dry ingredients into the wet ingredients, using the hand-held mixer to combine them on a low speed. Continue until the dough has come together.
6 Cut the dough into two even-sized pieces. Turn each out onto a separate sheet of plastic wrap. Press into a rectangular log shape, and cover.
7 Refrigerate for at least one hour.
Roll out and prepare the cookies
1 Once the dough and cranberry filling have chilled, remove both from the refrigerator.
2 Sprinkle flour over a flat surface. Sprinkle flour onto a rolling pin, as well.
3 Place the first dough log onto the prepared surface.
4 Roll out into a rough 12” x 24” rectangle until the dough is about ½” – ¼” thick. Trim up the edges to make the rectangle even.
5 Slather half of the cranberry filling into the rectangle, leaving about ½” space from the edges of the dough. (The closer the cranberry filling is to the ends, the more likely it will leak out in the rolling process.)
6 Starting on one of the long sides, slowly lift the dough and roll the cookies into a pinwheel. If the dough is sticking to the surface below, use a knife or pastry cutter to gently free it. Slowly roll the dough until a long pinwheel has been formed.
7 When the dough and cranberry filling have been rolled into a wheel, brush all sides with the egg wash.
8 Once the egg wash has been brushed on, sprinkle with additional sugar.
9 Transfer the cookie roll onto a baking sheet. Place the baking sheet in the refrigerator.
10 Repeat the process with the other rectangle of dough.
11 Let both cookie rolls chill overnight. (This step is very important. Please don’t skip it, as the longer the cookie rolls chill, the better chance the pinwheels have of keeping their circular shape.)
Bake the Cranberry Pinwheel Cookies
1 Preheat the oven to 350°F. Line two baking sheets with parchment paper or a baking mat. Set aside.
2 Remove the chilled, rolled dough from the refrigerator.
3 Moving quickly, slice the cookies. I sliced mine to be about ½” thick, and this thickness served them well, as they crisped up in the oven.
4 Place the cookies onto the prepared baking sheet.
5 When all the cookies have been sliced and arranged on the baking sheets, transfer the baking sheets into the oven. Transfer the remaining cookies/cookie rolls into the refrigerator to chill while the first batch bakes.
6 Bake for 15-17 minutes, or until the cookies have crisped around the edges and have turned slightly golden.
7 Remove from the oven, and let cool on a cooling rack.
8 Repeat the process, baking all of the cookies, until the dough has been completely used.
9 Enjoy slightly warm or at room temperature with a cold glass of milk!