Prep Time 20 minutes mins
Cook Time 10 minutes mins
Total Time 30 minutes mins
For best flavor, use block cheddar and grate it yourself so the cheese melts more smoothly and blends better with the cream cheese; be sure to drain the pimentos thoroughly so the filling doesn’t get watery, and if you prefer a stronger pimento cheese, make it a few hours ahead and refrigerate it to let the flavors meld, then bring it back to cool room temperature before filling the cups. The phyllo shells can be lightly pre-crisped in the oven for a few minutes before filling if they seem soft from the package, and you can easily customize the heat level by adjusting the cayenne or adding a few dashes of hot sauce. These can be served warm or at room temperature, but avoid refrigerating the fully assembled cups too long, as the shells can soften; instead, keep the filling chilled separately and fill and bake the cups shortly before serving.