Preheat your oven to 350°F (175°C). Line 8 wells of a standard cupcake or muffin tin with foil liners for easy cleanup.
In a food processor, combine all the cookie dough ingredients: the cut cold butter, almond flour, cocoa powder, instant coffee, 1/3 cup sweetener, gelatin, and vanilla extract. Pulse until a thick, uniform dough forms. It should come together easily.
Divide the dough evenly into 8 balls. Press each ball firmly into one of the foil-lined cupcake tin wells, shaping it into a cup.
Bake for approximately 18 minutes, or until the cookie cups feel slightly firm to the touch. Don't worry if they sink a bit in the centers – that's where the delicious filling goes! Let them cool completely in the tin.
While the cookies cool, prepare the rich toffee filling. In a medium saucepan, combine the 1/2 cup sweetener, heavy cream, and the remaining 1/8 cup salted butter. Cook this mixture over medium heat, stirring frequently, until it deepens to a beautiful golden brown color and thickens to a caramel-like consistency. This can take about 10-15 minutes, so keep an eye on it to prevent burning. Remove from heat and let it cool for about 10 minutes.
Once the cookie cups are cool, use a tart tamper or the back of a tablespoon to gently create a distinct indent (well) in the center of each one.
Carefully spoon the slightly cooled toffee caramel into the center of each cookie cup, filling the wells evenly.
For the chocolate topping, melt the sugar-free chocolate chips and the final 1 teaspoon of butter together. You can do this quickly in the microwave (stirring every 30 seconds until smooth) or using a double boiler.
Spread a thin layer of the melted chocolate over the top of each caramel-filled cookie cup. Let the chocolate set, either at room temperature or briefly in the fridge if you're in a hurry.