Line a baking sheet with parchment paper.
Slice the apples horizontally into ¼–½ inch thick rounds (about 10 slices total). Remove any seeds from the centers. Cut a small slit in the bottom of each slice and insert a popsicle stick.
In a microwave-safe bowl, heat the chocolate in 30-second intervals, stirring between each, until smooth.
Dip each apple slice into the chocolate, coating both sides. Shake off the excess and place on the prepared baking sheet.
Working quickly before the chocolate hardens, sprinkle with the chopped pecans. Let sit at room temperature until the chocolate fully sets.
In a microwave-safe bowl, combine the caramel squares and milk. Heat in 30-second intervals, stirring, until smooth and melted.
Drizzle the caramel over the chocolate-dipped apples. Sprinkle with flaky sea salt if desired.
Let cool until set. Enjoy!