In a stand mixer using the paddle attachment or a large bowl using a hand mixer beat the room temperature butter on medium speed until whipped. Add in the sugar and vanilla extract and then on low speed add in the dry ingredients (flour, cocoa powder, and salt). With a food processor add in the dried cherries and the chocolate. Pulse one or two times to chop up the pieces smaller and then add them to the dough.

Place plastic wrap on a clean work surface and put the dough on it. Form the dough into a log and wrap it up. Roll the wrapped dough on your work surface to create a uniform log and shape according to how big you want your cookies to be. Shortbread cookie dough can also be divided in half to create smaller cookies. Chill the dough for at least 2 hours or overnight until firm.