Preheat the oven to 350˚F (175˚C). Spread 2 cups of pecans out onto a large parchment-lined baking sheet. On a separate (small) parchment-lined baking sheet, spread 18 nice pecan halves (these will be for topping the cookies). Bake the pecans until they’re fragrant and a shade darker in color, about 5-7 minutes.

Transfer the 2 cups of toasted nuts to a food processor and let them cool for 5 minutes. Pulse the nuts until they’re finely chopped. Add the almond flour, psyllium husk powder, and sea salt, and pulse to incorporate. Pour in the coconut oil and maple syrup, and process until the mixture looks damp and clumps up along the side of the work bowl.

Form the dough into 1 ½ tablespoons-sized balls (about the size of a golf ball)—a small ice cream scoop makes this easy (see the tips). Arrange the balls onto 2 parchment-lined baking sheets, spacing them 2-3 inches apart (you should get about 16 balls). Using your hands, press the cookies into ¼-inch thick rounds. You can tidy up the edges with your fingers, but there’s no need to go crazy—the cookies will be mostly covered.

Bake the cookies, rotating the pans and switching their positions halfway through, until the edges and bottoms are golden brown, about 9-10 minutes. Set the pans on racks and let the cookies cool completely.

In the meantime, place the pitted dates in a heatproof bowl and pour enough boiling water over top to cover (if your dates are very fresh and sticky, use warm water instead). Soak for 10 minutes.

Drain the dates well, then transfer them to a food processor and pulse until chopped. Scrape the sides, and add ½ cup of coconut milk, along with the vanilla and salt. Process until smooth, stopping and scraping down the sides occasionally (this might take awhile, so just let the machine rip). The consistency should be thick and spreadable, like creamy nut butter—if it’s too thick, add a bit more coconut milk (this will depend on the freshness and size of the dates you used). Do Ahead: The date caramel can be refrigerated in an airtight container for up to 1 week.

Combine the chocolate chips and coconut oil in a heatproof bowl and microwave, stirring every 20-30 seconds, until smooth (alternatively, place the bowl over a pot of barely simmering water and cook, stirring often, until melted).

Dollop 1 ½ tablespoons of the date caramel over each cooled pecan cookie (use that same ice cream scoop!). You will likely have one extra cookie. Using the back of a small spatula or spoon, spread the caramel over the cookies, leaving a ¼- to ½-inch border (I like a nice mound of caramel in the middle, so don’t flatten it too much).

Spoon a heaping tablespoon of the melted chocolate over each cookie, using the back of a spoon to nudge it evenly over top so that it completely covers the caramel. This takes a bit of patience, but it can be fun if you lean into it (also, it’s okay if the chocolate drips over the sides!). Sprinkle the cookies with a bit of flaky sea salt, and garnish with one of the reserved toasted pecans.

Refrigerate the cookies until the chocolate is set, at least 45 minutes. Enjoy slowly, with delight!