1. a way of avoiding or escaping a rule, law, or requirement by exploiting an ambiguity or omission
2. a narrow opening in a wall, especially in a fortification, through which weapons can be fired
Usage: historical; military

Examples

• The wealthy businessman found a tax loophole that saved him thousands of dollars.
• Lawyers discovered a loophole in the contract that allowed their client to withdraw.
• The new law was carefully written to close existing loopholes.
• Congress worked to eliminate loopholes that allowed companies to avoid regulations.
• Medieval archers fired arrows through loopholes in the castle walls.
• The fortress had narrow loopholes for defense against attackers.