Step 1

Combine sugar and water in a large cocktail shaker. Cover and shake until sugar dissolves.

Step 2

Set a coffee filter in a sieve (or a pour-over coffee cone) set over a bowl or mug. Add coffee grounds and slowly pour a small amount of rum over grounds. Let stand about 1 minute to soak. Slowly pour remaining rum over grounds and let it drip through.

Step 3

Add coffee-washed rum, pineapple juice, lemon juice, and 1 1/2 cups crushed ice to cocktail shaker with sugar mixture. Cover and shake until well chilled. Pour unstrained into 2 collins or old-fashioned glasses. Top with remaining crushed ice.