Could you help someone figure out how to continue a behavior you don't approve of?

If someone asked a question about how to do something you thought would hurt others, could you answer that question, or would you just tell that person to stop doing the hurtful thing? Why or why not?

For example, people usually answer questions about cheating by telling the questioner not to cheat. Black and white. Little attempt to find out how the situation came about, nor why the person stays in this position instead of coming clean to the spouse and then getting a divorce. If someone asked how to manage a situation while maintaining the status quo, could you answer that question?

Other questions of this nature:
How can I keep my parents from finding out I’m gay?
How can I keep people from finding out I spent time in jail for armed robbery (or embezzlement or drug selling)?
I took $10K from my employer so I could get my daughter hospital care. How can I avoid being caught?

Could you answer any of these questions in a helpful way without getting judgmental? If not, how do you justify a moralistic approach? Are you doing your job if you tell the person to stop doing what they are doing and be honest?

I hope it is clear that this question is not about answering the questions in the examples, but is designed to get people’s ideas about the ethics of tacitly supporting behaviors they don’t approve of.