In a small saucepan, bring sugar, water, sliced habanero, and ginger to a boil. Once mixture comes to a boil, lower the heat to a simmer and let simmer for about 10 minutes.
Pour simple syrup into a heat-proof jar or container, straining the habaneros and ginger out, and place in the fridge to cool.
On a small plate, mix together cinnamon and coarse sugar. Brush a little apple cider around the rims of your cocktail glasses and dip glasses into cinnamon/sugar mixture. Fill glasses with ice.
In a cocktail shaker filled with ice, add 2 oz. habanero ginger simple syrup, apple cider, and rum. Shake to combine and pour into prepared glasses.
Garnish glasses with an apple slice.