Orange Cranberry Cream Cheese Thumbprint Cookies

Make the dough
2 In a large bowl, cream the cream cheese and granulated sugar together using a hand mixer or a stand mixer.
3 Add in the egg and vanilla extract. Beat those into the batter then pour in the milk and white vinegar. Stir until combined.
4 In another bowl, sift together the flour, baking powder, baking soda and salt.
5 Sprinkle the dry ingredients the wet ingredients, mixing until completely incorporated.
6 Line a baking sheet with wax paper, and set aside.
7 Use a tablespoon cookie scoop (or a regular tablespoon measuring spoon) to measure out the cookies.
8 Roll the dough into balls using your hands.
9 Place the rolled dough onto the prepared baking sheet. They do not need to be spaced out because they will be chilling on this sheet pan, not baking.
10 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
13 In a small bowl, combine the cranberry sauce with the orange zest.
14 With a spoon, stir until the ingredients are incorporated.
15 Refrigerate until time to use.
Bake the cookies
18 Preheat the oven to 375°F. Line a large baking sheet with parchment paper or a nonstick baking mat.
19 In a medium-sized glass bowl, combine the granulated sugar and orange zest to make the orange sugar.
20 Remove the chilled dough balls from the refrigerator.
21 Transfer the chilled dough into the orange sugar and toss until coated.
22 Place the cookie dough onto the prepared baking sheet, spacing them 1-2" apart.
23 Repeat the process until all the cookie dough balls are coated in orange sugar and placed on the sheet pan.
24 Bake the dough for 8 minutes.
25 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.
26 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. Do not worry about them all being uniform.)
27 Bake for an additional 5-7 minutes, then remove from the oven.
28 Cool completely on a wire cooling rack before serving with a glass of milk!