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

I would put him on a focused remedial PT program. If he isn’t going to try and wants to fail himself it wouldn’t be with my help. If after being on a focused remedial PT program he still fails well then so be it but I would definitely try to square him away

Do your time and do your best. Don’t be a baby. Don’t leave like a jerk.

I'd have sprung for a ticket to the buffet bar and told him to enjoy himself while I started the separation paperwork. This is a volunteer military and people can decide they don't like it, and if eating their way out is an option, why not? The government can cancel an enlistment contract on a whim, so somebody taking advantage of a non-punitive regulation to get out seems fair. Some might say that's wrong, to let somebody game the system. My question is "How would attempting to retaining or motivate this sad sack inure to the benefit of the Army?" When manpower announces drawdowns this is a great time for commanders to get rid of all the "low hanging fruit" in their organization. If the soldier has been on active duty more than two and a half years, the DoD has recouped the cost of his training, he gets an honorable discharge and goes to work at Jiffy Lube and everybody wins. How he feels about his life going forward isn't my concern, my concern is providing the best possible work environment I can for the people under my command, and one unmotivated troop can do a lot of damage to esprit d'corps and morale.

Bye.

Bye.

Have him medically evaluated by a physician and head shrink and try to get to the bottom of this, the soldier may be having marital problems or family issues no telling, hope he can get the help he or she needs

Sir,
You really didn't provide much insight to the total picture. While this may appear to be a disgruntled Soldier, what else was going on with his personal life? The two sides of this debate are the Bad Soldier and the Bad Leader. I don't believe the leadership in this case is bad, I think they are more likely to be inexperienced. I don't believe this Soldier to be a bad Soldier but rather not properly cared for (Competence is my watch-word. My two basic responsibilities will always be uppermost in my mind--accomplishment of my mission and the welfare of my soldiers. ... All soldiers are entitled to outstanding leadership; I will provide that leadership. I know my soldiers and I will always place their needs above my own. I will communicate consistently with my soldiers and never leave them uninformed.) by his NCO leadership. If the leadership has been diligent and knows the Soldier, he may not have gotten where he is emotionally. It is still a possibility that this Soldier is not adjusting to military life and may need to be separated for the good of the service.

One course of action, without knowing the specifics of the situation, would be to reassign the Soldier to another team or platoon and give the new leadership team time to acclimate if you will. If the Soldier fails to adjust then separation options may need to be considered.

This exact thing happened in my unit in 1998. The Soldier was skinny but decided this was the quickest way out as he didnt want to do his remaining 3 years.
He got it done too.
Two years later he come by the barracks all proud of his return to normal size and job working construction.
He was in another platoon so I dont know what steps his leaders took but I do know the 1SG didnt handle it so well. Outright yelling in formation and such. 1SG didnt make SGM either.

When I was in the first time it was tell them you are gay I have seen soldiers use the weight routine to get out.

If you quit, no matter what reason, you will regret it the rest of your life. Unless of course you find it easier to quit then to give it your best to succeed. Dave