“I'm going to fail height-weight on purpose and get booted” – how would you handle this?

I consider this the same as writing a bad check knowingly. I would counsel the individual as to his obligation to honor his signed word. If he continues to fail on purpose I don't see any other option than to initiate disciplinary action. Time for the young man to suck it up and fulfill his obligation or bear the negative consequences.

I'd say good luck with that. It is at the command's discretion to initiate a discharge. In my 18 years, I have never seen some one discharged for not passing at PT test. I would of course want to find the reason why. From there I would encourage to do what they need to, to get through their enlistment but also remind them that failing height/weight and PT have some adverse actions. First and foremost they lose whatever leadership position the hold and responsibility the hold. They also will probably end up on the crap details and be the "b*tch" of whatever the unit is involved in. NTC- white cell, field conditions- KP for example. Make them understand that they do have value other than the very basic soldiering but they will lose their credibility for a failing standard. Also let them know that is the commands responsibility to mentor and develop soldier who are wanting to progress in their career. If the soldier is not a complete dirt bag, then that will strike a cord with them. If he is then staff duty has a person who can mop floors for them.

Well, its obviously the soldiers choice sadly. However a true soldier/sailor/airman/marine would fulfill their duty and obligation to the army. Speaking for myself, i WISH i could have stayed in. Although my physical ability deteriorated so i could no longer serve. I finished my duty to the army but was unable to re-up. So for anyone that wants to get out by "cheating the system" is unworthy to even wear the uniform. The military is a tough lifestyle, everyone should know this off the bat and if you cant imagine the worst things that could be, then you shouldnt bother signing your life away. There are plenty of soldiers that would probably love to re-up like myself but cannot and its a shame that others are willing to give it up.

The way you did. Discuss the implications of a general or administrative discharge and offer him support to meet standards. If he refuses, take the required action to discharge him.

ARMY
STRONG
NOT
ARMY
WHINE!!

Go.home.Bad4.morale.suck.it.up.
You're going 2.regret.this.move.

Had them over to someone like me - if I can't fix him I kill em trying. All I need is a entrenching tool and good solid ground.

Reported him to the battalion CO.

Honestly some really great responses already given. My two cents would be to have this guy talk to someone that overcame this problem. Preferably a peer or someone 1 or 2 ranks above him that he respects. See if there are any NCO's that had a really rough time as jr enlisted that can mentor this soldier. To people that really struggle with the self control and self discipline of weight control issues, the goal of losing weight and getting back in shape has to seem achievable TO THAT PERSON.
You can't tell someone that's down on themselves that something isn't that hard if they cant see it on their own.

As to why he feels this way in the first place? I can only speak to my personal experiences. He might feel trapped. He might feel that he has zero control over his life. He might have told himself that he wont be happy unless x, y, or z happens, but x, y, and z are unattainable while he's serving where he is. (Example, he wants to be with a girl but said girl lives in an area that he can't get stationed or his favorite things to do are snow related but he's stationed in the south)
Sometimes people overeat because that's the only thing they feel like they have any real control over. Maybe you could try giving him some responsibilities so he feels more apart of the team or make him aware of an opportunity that's aligned with his interests that makes him WANT to improve himself.

Barring that, i'd let the guy know that everything he endured and earned would be for pretty much nothing if he gets separated in that way. Tell him all of the benefits he would lose. Ask him what he's going to do for a steady paycheck.

I would have given him a counseling and sent him to see the psych. Then make him tell the truth. he was trying to get out for a specific reason and didn't want anyone to know. Fine, but to gain weight was only hurting himself and no one else. A section 8 is what he would have ended up with and that is worse then a dishonorable. He could have even gotten both.