Soak the dates. In a small bowl, cover the pitted Medjool dates with the boiling water and let soak for 15 minutes, until softened. Spoon 2 tablespoons of the soaking water into a blender, then drain and discard the rest, so only the softened dates remain.

Blend the chocolate caramel. Add the softened dates to the blender (with the 2 tablespoons of water already in there), along with the maple syrup, vanilla extract, maple extract, 1/4 cup cocoa powder, and salt. Blend until completely smooth and thick, like a fudgy, sticky chocolate paste, stopping to scrape down the sides as needed.

Firm up the dough. Transfer the mixture to a bowl, scraping the blender well to get out as much as possible, and stir in the blanched almond flour, adding more by the tablespoon as needed, until the dough is firm enough to hold a shape without sticking to your hands. Date moisture varies, so this amount can shift a little.

Chill the dough. Chill the dough in the fridge (not the freezer) for 20 to 30 minutes—just until it's easy to handle. You want it firm enough to shape but still pliable, not hard.

Shape into balls. Even after chilling, the dough stays a little sticky—dust your fingers with cocoa powder before scooping and rolling each ball, and sprinkle a bit over the dough itself, too, as you work. Pinch off about 1 tablespoon of dough and roll it between your palms into a bite-size ball, about 1 inch across. Repeat with the remaining dough (makes about 20), re-dusting your hands as needed. Lightly sprinkle optional cocoa powder over the balls.

Chill and store. Chill the shaped candies for at least 30 minutes, until firm to the touch and chewy rather than sticky. They'll keep in an airtight container in the fridge for up to a week.