Is rebuking a sinner once enough?

Question:

Hi, I was reading your article How do I tell someone they are sinning? and I wanted to ask a question concerning Galatians 6:1. When correcting another Christian about a sin, does one have to continue until they stop or try and leave the rest up to God?

Answer:

It would be a rare case where you can speak to someone about his sin and he would listen to you the very first time. As I pointed out in the answer, you typically will need to chip at the problem a little bit at a time and give him time to think about your point. There is nothing in Galatians 6:1 that indicates once is enough; in fact, it is worded as an ongoing task. "Therefore, as we have opportunity, let us do good to all, especially to those who are of the household of faith" (Galatians 6:10). Doing good is not limited to monetary help. Spiritual help is of far greater value.

Now, that doesn't mean you are to make a pest of yourself -- that would not be teaching with a gentle spirit. However, until the person is restored the task of helping him see the need to return remains before you. Opportunities will frequently arise and we should take advantage of them to nudge a person back to the truth.