Add the sugar to a medium saucepan over medium heat, stir continuously with a spatula. Be patient, it will take a little bit to melt but you want to take it low and slow.
Once it has melted into a light brown sauce, quickly whisk the room temp butter 1 tbsp at a time.
Add in eggnog. If your caramel seizes up and hardens, keep whisking over low heat, it may take a few minutes but be patient it will come back together.
Allow to cool to room temperature and set aside for later. Store any leftovers in the refrigerator.
Eggnog Cookies
Preheat oven to 350F.
In a small bowl combine the sugar mixture for rolling the dough. Set aside.
In a large bowl combine butter, brown sugar, and granulated sugar. Mix until light and fluffy.
Add in egg, eggnog, and vanilla extract. Mix to combine.
Add in flour, spices, baking soda, and baking powder. Mix to combine.
Scoop out 12 equally sized cookies and roll into sugar mixture from earlier. Set onto a prepared baking sheet.
Bake for 10-12 minutes. Allow to cool on baking sheet for 10 minutes.
While cookies are baking make frosting. Combine butter, powdered sugar, cinnamon, and nutmeg in a large bowl. Mix until well combined. Add in eggnog 1 tbsp at a time until the desired consistency is reached.
Once cookies are fully cooled, pipe a buttercream border around the edge of half of the cookies. Fill the center with eggnog caramel, and top each with remaining unfrosted cookies.