Remove the rind from one orange and add to a small saucepan with 1 cup heavy cream. Bring to a simmer over medium heat or until bubbles appear at the edge of the pan. Once heated through and edges barely bubbling, remove from heat and cover, allowing to steep for minimum 30 minutes.
Return the cream to heat and warm it through, taking care not to let it boil. Strain out the orange peel while pouring over the chocolate.
Begin stirring to melt the chocolate. If lumps remain after several minutes of stirring, can microwave on 30 second increments and use residual heat to fully melt all chocolate.
Zest half the second orange and add to the ganache. Mix to incorporate.
Fill each cookie cup with orange chocolate ganache, evenly distributing between all cookies.
(Optional) Use a citrus peeler or knife to cut orange curls for garnish, if desired. It works best to add the peels before the chocolate ganache has set completely.