It can mean two things: 1. When someone walks with something not very clear, doubtful, not very credible2 . It is used to indicate actions performed secretly from others, behind the backs of others, treacherously Some synonyms, words or similar expressions can be between dark and light, when everyone sleeps
The meaning of the phrase "Between roosters and midnight " it is said that its origin comes from the fact when Jesucristo was tried by the Sanhedrin and the priests, Pharisees " between midnight and the crowing of the cock " ( between 12 am and 3 am about ) in where in a time of " darkness " prepared the ruse to find him guilty of crimes he did not commit, so that these Jewish priests could take advantage at a time where many " sleeping " so no one could defend it and thus realize their plans to condemn it. In the popular, especially in the language Spanish and Latin American slang, the phrase was popularized as "Between roosters and midnight " its meaning refers to when a or several people are plotting something secretly and they do it in a little light or visible atmosphere and even probably at inappropriate hours where there are few people ( many times in the early morning, ) to use a fraudulent means, in order to achieve to get with it and that other people can be affected, have little chance of doing something about it.