Preheat the oven to 350-degrees Fahrenheit, and lightly spray a 9” round springform pan with cooking spray. You can also use a regular round cake pan, but be sure to spray it very well. If the pan isn’t nonstick, line the bottom with a circle of parchment paper.
Slice the softened butter and add it to a medium bowl. It should be soft to the touch, but not room temperature. Add the powdered sugar, honey, and vanilla extract. Beat on medium speed with an electric mixer until homogeneous, about 1 minute.
Next, add the flour and beat until just combined. Do not over mix.
Transfer the dough to the cake pan. Dip your fingers in flour, and use them to push the dough out into an even circle. It should be about 1/4” thick. It is important to ensure an even height across the pan.
Next, prick the dough all over with a fork, about 25 times.
Place the cake pan on a baking sheet, and bake for 32-34 minutes. Do not be afraid of a golden brown color—this is what gives the cookies caramel and the best flavor.
Let the shortbread cool for 1 minute, then pop open the springform pan (if using). Using a pizza wheel, cut the dough into 8 or 10 slices, however big you like your shortbread cookies. If using a regular cake pan, careful tilt the shortbread out of the pan, and then remove the parchment paper. Slice into 8-10 slices.
Let the shortbread cool completely.
In a small glass bowl, add the chocolate and coconut oil. Pulse in the microwave for 20 second pulses, stirring between each pulse, until the chocolate is almost melted all the way. Remove it from the microwave, and stir to melt the chocolate fully—the heat of the bowl should melt it completely.
Dip each shortbread cookie in the chocolate, and move to wax paper to set. To speed up setting, place in the refrigerator to set.