You've thought it through pretty well and sound like a rational and reasonable parent. Hopefully he will be as reasonable and willing to sit down and talk. I went through the same things during my late high school and early college years. The appeal seemed to be more social/peer pressure than the feeling I got. Several ideas pop into my mind as discussion openers or topics: 1) Ask him what he feels when smoking. Find out if he thinks it feels good, weird, scary, whatever. Share your memories of what you felt and why you didn't keep smoking. 2) Ask why he smokes. Is he having some social or emotional problems he wants to escape? 3) Look at it from the legal standpoint. Find out if he is aware of the penalties if he's caught in possession, driving, selling, buying, etc. Talk a bit about how a record (he's nearing having an adult record instead of juvenile) can affect his future. There are many jobs that, with even one mention of drug use in the past, will be closed to him. 4) Along the lines of "controlling what you can" you might consider allowing him to smoke only at home. I'm not endorsing this idea, but many families allow their children to do things in the privacy of their own home so that they can keep an eye on the situation. Most find that it tends to de-glamorize the activity since the kids are no longer trying to get away with something! Any communication at this point is a good thing, and keeping the door open to discuss freely without recrimination is the way to go. Many times teens make decisions based on what they hear from their friends (laws, medical effects, etc.) and if you become the expert and are sympathetic you'll be a hero!