If you dream of a leaking leaky roof, it may mean bad news. The dream interpretation of a leaking roof/ ceiling is that money will be lost. Money may be lost in some ways. Firstly, money will be spent on repairing the leak. Secondly, this dream symbol hints of loss of cash in other areas like work, failed project, or maybe a customer who declines to pay for services already rendered & etc. Thirdly, a leaking roof drips water, which will cause damage to the house, and the material possessions inside it.