Orange Cranberry Cream Cheese Thumbprint Cookies

Make the dough
1 In a large bowl, cream the cream cheese and granulated sugar together using a hand mixer or a stand mixer.
2 Cream together, and then add in the egg and vanilla extract. Beat those into the batter before adding the milk and white vinegar, which will be stirred in, as well.
3 In another bowl, sift together the flour, baking powder, baking soda and salt.
4 Sprinkle the dry ingredients the wet ingredients, mixing until completely incorporated.
5 Line a baking sheet with wax paper, and set aside.
6 Use a tablespoon cookie scoop (or a regular tablespoon measuring spoon) to measure out the cookies.
7 Using your hands, roll the dough into balls.
8 Place the rolled dough onto the prepared baking sheet. (You don’t have to space them out because they will be chilling like this.)
9 When all the dough has been rolled into balls, cover the baking sheet with plastic wrap, and chill for at least 1 hour.
Mix the filling
1 In a small bowl, combine the cranberry sauce with the orange zest.
2 With a spoon, stir until the ingredients are incorporated.
3 Refrigerate until time to use.
Bake the cookies
1 Preheat the oven to 375°F. Line a baking sheet with parchment paper or a nonstick baking mat.
2 In a medium-sized glass bowl, combine the granulated sugar and orange zest to make the orange sugar.
3 Remove the chilled dough balls from the refrigerator.
4 Using your hands, place the chilled dough into the orange sugar. Toss the dough until completely covered in the orange sugar.
5 Place the cookie dough onto the prepared baking sheet, and repeat until the cookie dough has all been coated in the orange sugar.
6 Bake the dough for 8 minutes.
7 Remove the baking sheet from the oven. Use a kitchen instrument (like the back of a cookie scooper or the non-muddling end of a muddler) to press “thumbprints” into the warm cookies.
8 Scoop a heaping 1/2 teaspoon of cranberry sauce into each indention. (Some will be larger or smaller, depending on how you make the indention.)
9 Bake for an additional 5-7 minutes, then remove from the oven.
10 Cool completely on a wire cooling rack before serving with a glass of milk!