Plan Ahead - this recipe calls for chilling the dough. Also take the butter out of the refrigerator ahead of time.
Add the cranberries and ¼ cup sugar to the bowl of your stand mixer and mix on medium high speed. This will help in breaking up the cranberries into smaller bits.
Add butter and ½ cup more of sugar to the mixer and mix at high speed till the mixture is light and creamy.
Now add the vanilla, orange zest and juice. With the mixer running on low speed, carefully add the flour, ½ cup at a time. Mix until the dough comes together. (See notes)
Cut a piece of plastic wrap and lay it on your kitchen counter. Dump the dough out on the plastic wrap and shape into a smooth log about 1.5 inches wide.
Wrap the dough completely, fold the ends of the plastic wrap and put it in the refrigerator to chill for at least two hour and upto 24 hours.
After the dough is chilled, take it out and preheat your oven to 325 degrees F or 163 degrees C. Put parchment paper on 2-3 cookie sheets.
Unwrap the dough log and using a very sharp knife, cut it into ¼ inch thick slices. Roll the cut slices into remaining sugar and lay on the cookie sheet.
Bake the cookies for about 12 minutes, rotating the cookie sheets at about 6 minute mark. I also switch the cookie sheets among different rack positions at this time so that they bake evenly.
Take the cookies out of the oven and let cool in the cookie sheet for 5 minutes before removing to a cooling rack and letting them cool completely.
Enjoy the cookies yourself or pack them in little baggies or boxes to share with friends and family.