It expresses determination to continue, against odds or hardships. The team's efforts to keep the flag flying inspired the whole town during the crisis.
Pro Tip 2/3
Success Continuation
Used when someone persists in actions to maintain success. After the award, she worked harder to keep the flag flying.
Pro Tip 3/3
Not Literal
The phrase doesn't involve an actual flag but symbolizes an ongoing effort. His recovery from injury showed he would keep the flag flying.