Classic movie candy, made vegan!
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Line a cookie sheet with parchment paper, set aside. Combine all ingredients (except vanilla, chocolate, and shortening) in a medium-sized saucepan and bring to a low boil over medium heat, stirring frequently.
Cook the mixture to firm ball stage, 248°F. If you don’t have a candy thermometer, you can test for soft ball stage by dropping a spoonful of caramel into a glass of cold water. If it holds its shape and produces a squishy ball, it’s at soft ball stage. Cook for a 2-4 minutes longer to achieve firm ball stage.
Remove from heat and continue stirring until the mixture stops bubbling. Stir in vanilla.
Drop about half teaspoon portions of caramel onto the lined cookie sheet until all the caramel is used up (or pour leftovers into a large mass, sprinkle with salt, and cut into salted caramels!). While the caramel is still hot, it will probably flatten into discs.
As the caramel cools, you can roll the discs into balls if you’d like. They don’t have to be perfect; they’re called Milk Duds for a reason.
When the caramel is completely cool, dip them in chocolate. Melt the chocolate and shortening together in the microwave or on the stove using a double boiler method.
Dip the caramels in the chocolate, remove with a fork, and place back on the parchment-lined cookie sheet to cool. Repeat with all the caramels.