In paragraph 6 what does the phrase "drew him on by artful questions" mean?

questioned him sincerely

questioned him to waste time

questioned him to gain his trust

questioned him to try to gain privileged information

In paragraph 9, what the phrase "drew him on by artful questions" means is that he questioned him to try to gain privileged information.

He had to find out some information that was very important to him, so he started questioning him furtively so as to get to the bottom of things.