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Hours of troubleshooting were fruitless in resolving the technical issues with the software.
Despite their exhaustive search, the quest for the missing treasure proved fruitless.
The farmer's efforts to revive the withering crops were fruitless due to the prolonged drought.
The attempt to reconcile their differences was fruitless, leading to the decision to part ways.
The negotiations with the opposing party proved to be fruitless as they were unable to reach a compromise.