Pulse coconut flakes in a food processor until small pieces. Combine coconut flakes, flour, and salt in a bowl. Toss together to combine.
Pour sweetened condensed milk and vanilla over dry ingredients and stir with a spatula until thoroughly combined. The mixture should be wet, but come together.
Scoop cookies directly onto a parchment lined baking sheet that has been lightly greased with cooking spray. Flatten each mound with the back of a measuring cup. Make a well into the center of each cookie using the back of a teaspoon.
Spoon a dollop of cherry pie filling in the center of each cookie (about 2 cherries per cookie.)
Bake at 350 degrees Fahrenheit for 12 to 15 minutes or until golden brown. Cool completely.
Melt chocolate chips with shortening in a bowl, using short bursts in the microwave. Start with 30 seconds. Stir. 30 seconds. Stir. 15 seconds. Stir. Etc. until melted. Do not burn the chocolate!
Dip the bottom half of the cooled macaroons in the chocolate. Scrape excess chocolate off the cookies with the side of the bowl, and place the cookies back onto the parchment paper.
After dipping all of the cookies, put the remaining melted chocolate into a zip-top bag and cut off the corner. Squeeze the bag of chocolate over the top of the cookies in a zig-zag pattern.
Allow all chocolate to set before consuming or packaging the cookies to gift to neighbors/friends. To speed this process along, place pan of cookies into the refrigerator until set.