1. ways of avoiding or escaping a rule, law, or requirement by exploiting ambiguities or omissions
2. narrow openings in walls or fortifications through which weapons can be fired
Usage: historical; military

Examples

• The wealthy businessman found several tax loopholes to reduce his payments.
• Congress closed the loopholes that allowed companies to avoid environmental regulations.
• Her lawyer discovered loopholes in the contract that favored her client.
• The new law was carefully written to eliminate potential loopholes.
• Medieval castle walls had loopholes for archers to shoot through.
• The fortress defenders fired arrows through the narrow loopholes.