Start by preheating your oven to 325°F. Line two baking sheets with parchment paper to prevent sticking. Set aside for later.
Measure out your cherries, pat them dry with a clean towel, and set them aside.
In a mixing bowl, whisk together the flour and sugar. Cut the cold butter into small pieces and add it to the bowl.
Use a pastry cutter or two forks to combine the butter into the dry ingredients until the mixture looks crumbly.
Add in the vanilla extract and the cherries. Then, use your hands to knead the dough until it comes together into a solid ball.
Scoop out small amounts of dough (about 1 tablespoon) and roll them into 1-inch balls.
Place them on your prepared baking sheets. Take the bottom of a drinking glass, dip it in sugar, and gently press down on each dough ball to flatten it to about 1/2 inch thick.
Place the baking sheets in the oven and bake for 10-12 minutes, or until the cookies have slightly risen and the edges start to pull away from the sides of the cookies.
Let the cookies cool slightly, then enjoy! You can also dip them in melted chocolate for a fun twist.
Notes
This recipe makes a lot of cookies. You will get roughly 50 bite sized cookies.
Cookie dough can be made up to three days in advance.
For a softer cookie, bake 10 minutes. If you would like a more crunchy cookie, bake the full 12 minutes.