Soak 12 pitted Medjool dates in a bowl of your hottest tap water for 10 minutes. This softens them for easier blending. Drain completely and add to your food processor.
Add 2 tablespoons maple syrup, 2 tablespoons cashew butter, 2 tablespoons almond flour, 1/4 teaspoon salt, 1 teaspoon vanilla extract, and 1 tablespoon coconut oil to the food processor with the dates. Pulse several times to break up the dates, then blend on high until well incorporated. Scrape down the sides and mix several times as needed.
Line a 4x8 inch bread pan with parchment paper and spread the caramel mixture evenly. Freeze for at least 1 hour until completely solid. This makes cutting into clean squares so much easier.
A few minutes before removing the caramels from the freezer, melt 1 cup dark chocolate chips and 1 tablespoon coconut oil in 30-second intervals in the microwave, stirring between each interval, until smooth and completely melted.
Remove the caramels from the freezer and lift out using the parchment paper. Cut into squares. Dip each square in the melted chocolate and place on a parchment-lined cookie sheet. Sprinkle with flaky sea salt while the chocolate is still wet.
Return the dipped caramels to the fridge or freezer to set the chocolate coating completely before serving.