First, prepare the caramel. Over medium low heat (about a cook level of 3 or 4 on a burner is ideal) , heat your sugar until it has caramelized and achieved a nice amber color. You don’t want it to be super dark.
Once golden brown, remove from the heat and add the butter. Be careful when you add the butter, as it will bubble and steam a lot! Carefully whisk (I like using a fork) in the butter until it has melted completely into the caramelized sugar. You want it to be smooth and fully incorporated. Keep whisking if there is any separation.
Once combined, then add in the coconut milk and whisk until once again it has become fully incorporated and homogeneous. If it is being a little stubborn and not coming together well, place your pan back on low heat and continue to whisk.
Once smooth and it has the texture you would like, set aside to cool completely.
Now, for the cookies. Preheat the oven to 350. Add the butter and both sugars to a bowl (or to a mixer if you would like, but keep it on low speed during the whole process) and begin to work the butter into the sugar until creamy.
Next, add in the egg yolks and vanilla extract and mix well, again until creamy and smooth.
Lastly, add in the flour, remaining dry ingredients, and mix until the dough comes together.
Line a cookie sheet with parchment paper. Using a big cookie scoop (3 tbsp), scoop out the dough and place on the cookie sheet, leaving a good amount of space in between each cookie. Bake for 13-14 minutes. You want them to have just a slightly golden bottom. Don’t over-bake or you will lose the delicious chewy texture! Let them cool completely.
Now for the frosting. By hand, or with a mixer on low speed, cream the butter until smooth.
Then, add in the powered sugar and vanilla and cream together until smooth and creamy. I have found the most success with dairy-free buttercream when mixing by hand. Dairy-free butter can become soft very quickly when using a mixer, so just go slow and err on the side of under-mixing to begin with.
Lastly, let’s assemble the cookies! Generously pipe on the frosting to the top of the cookie, then pipe on a small amount of your dairy free caramel. I find it helpful to pipe the frosting in a ring, or circle shape around the top of the cookie, leaving the middle unfrosted. This makes a nice little crevasse for the caramel so it doesn’t slide off the cookie. Finish the cookies off with a generous dollop of apple pie filling on top.