In a large mixing bowl using an electric hand mixer beat the butter until creamy. Add in milk, vanilla, and cherry juice. Mix again. Mix in powdered sugar 1/2 cup at a time. The mixture should resemble a crumb and will come together if mashed. If it's too dry add a little more cherry juice and mix again. Form a solid dough ball with your hands. Cover with plastic wrap and refrigerate for 30 minutes.
Prepare cherries
Remove cherries from jars and place on paper towels. Blot with extra paper towels to remove excess juice. (If you can find cherries with the stems on them use them. It's ok if you don't find them.)
Cover the cherries
Using a 1/2 tsp (I like to use the smallest end of a melon baller) scoop out dough. Roll dough into a small ball. In palm of your hand push dough ball into a flat rounded disc shape. Place a cherry in center of disc and start forming the dough around the cherry. The dough should be very pliable. Cover the cherry upto the stem. If no stem, then cover the whole cherry. Place onto a sheet pan lined with parchment paper. Finish covering the rest of cherries.
Prepare chocolate
There are several ways to melt chocolate. I tend to use the double boiler way to have a consistent smooth chocolate. Bring a pot of water to a boil (I fill pot about 1/3 of the way with water). Place a heat resistant bowl onto the pot. Add the chocolate chips and Crisco shortening. Stir continuously until chocolate has melted and is nice and smooth and has thinned out.
Cover Cherries
Pick up cherry by the stem and drag through the chocolate to coat entirely up to the stem. Place onto the parchment or wax paper lined sheet pan. Or you can directly place them into little 1 1/2 inch paper cups used for candy. For a quick setting of chocolate, after all cherries are covered, place sheet pan in freezer for 30 minutes to an hour.
