Special equipment: a skewer, instant-read thermometer and plastic piping bag
Position an oven rack in the center of the oven and preheat to 325 degrees F. Line a baking sheet with parchment.
Whisk the flour, baking powder and salt in a medium bowl. Beat together the butter and sugar with an electric mixer on medium speed until light and fluffy, 5 to 7 minutes. Add the egg and beat to combine. Slowly add the flour mixture and beat on low until the dough is just combined. Transfer the dough to a floured work surface and press it into a rectangle. Wrap in plastic and refrigerate for at least 30 minutes.
Roll the dough out on a lightly floured surface to about an 8-inch square that is 1/4-inch-thick. Cut the dough into quarters, then cut each quarter into 8 sticks using a straight edge or sharp knife. (Each cookie will be about 4 inches long and 1/2 inch wide.) Use a skewer to make 3 holes on the top of each cookie about 1 inch apart. Transfer the cookies to the prepared baking sheet.
Bake, rotating the pan from front to back halfway through, until golden, 25 to 28 minutes. Allow to cool completely on the baking sheet, then transfer the cookies to a wire rack.
Meanwhile, combine the chocolate and canola oil in a small microwave-safe bowl and melt in the microwave in 30-second intervals, stirring after each. With a butter knife or offset spatula, spread the chocolate on the bottom of each cookie and set them chocolate-side up on a rack. Refrigerate until hardened, about 20 minutes. Turn the cookies over.
Combine the caramels and heavy cream in a medium microwave-safe bowl and melt in the microwave in 30-second intervals, stirring after each interval, about 2 minutes. Let cool until the mixture registers 100 degrees F on an instant-read thermometer, then transfer to a piping bag. Cut the tip of the bag and pipe a strip of caramel on the uncoated top of each cookie. (If the caramel strips look messy, use your hand to mold and straighten the lines -- at this point, the caramel will be very malleable.) Return the cookies to the rack caramel-side up and refrigerate until hardened, about 20 minutes.
Spoon the chocolate over each cookie or dip the caramel side so that it is completely covered with chocolate. After the cookies are completely coated, drizzle the chocolate with a spoon back and forth crosswise over each. Return to the wire rack until cooled and the chocolate hardens, about 2 hours. Store in an airtight container up to 5 days.
When measuring flour, we spoon it into a dry measuring cup and level off the excess. (Scooping directly from the bag compacts the flour, resulting in dry baked goods.)
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