For the chocolate ganache
Place chocolate chips and cream in a medium microwave safe bowl. Microwave on high for 1 minute. Stir until completely smooth. Heat for 15 more seconds, if needed. Stir in vanilla. Set aside.
For the crust
Preheat oven to 350°F. Place flour, salt and granulated sugar in a food processor. Pulse a few times. With processor on, add butter, one cube at a time. Add 4 Tbsp water and pulse several times, if dough doesn't come together, add remaining 1 Tbsp water. Shape dough into 2 (5-inch) disks. Cover each with plastic wrap and chill 1 hour.
Line two large cookie sheets with parchment paper. Working with 1 disk at a time (keep other in fridge to chill), roll dough out onto a floured surface to about 13 by 11-inch rectangle, then trim edges to get a 12 by 10-inch rectangle. Then cut into eight 5 by 3-inch rectangles.
Arrange 4 of the rectangles, spaced evenly apart on prepared baking sheet. Spread 1 Tbsp of ganache on center of each rectangle, leaving about a 1/2-inch border. Brush edges with a little water, then add another rectangle and seal with a fork around the edges. Prick top with a toothpick. Repeat process with remaining disk of dough.
Bake pop-tarts until light golden brown, about 20-25 minutes. Let cool.
For the topping
Toast coconut by spreading out on a baking sheet with a rim and placing in a 350°F. oven for 7-9 minutes (watch closely, it burns easily). Let cool. Place caramel and cream in a microwave safe bowl. Microwave on high for 1 minute and 20 seconds. Stir until smooth. Add coconut and stir until combined. Add more cream if it's too thick. You can also microwave for a few more seconds if it gets too thick. Very carefully spread on to cooled pop-tarts. (The pop-tart crust is flaky and delicate. If you puncture a hole in the crust, don't worry, just cover it with the caramel coconut spread.)
For the chocolate drizzle
Place remaining 1/2 cup chocolate chips and 1 teaspoon shortening in a small microwave safe bowl. Microwave on high for a minute. Stir until smooth. Pour into a small resealable plastic storage bag. Cut a tiny corner of the bag and drizzle over pop-tarts. Place pop-tarts in fridge for chocolate to set, about 20 minutes. Store covered in the refrigerator for up to 1 week.
Crust recipe adapted from CookingClassy.com