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

Let him go, wouldn't cover mine, or anybody else's 6 anyway!

If a soldier gets to the point where they'll accept a discharge on weight control failure or similar, then it's a failure of leadership. There's a good chance that the soldier did their homework and realized they will get an honorable discharge and maybe even cash to get out. Compare that to piss-poor leadership and it becomes a viable option.

Simple equation: Do nothing and get paid and an honorable discharge, or work hard to get fit and continue to deal with the ass-hat leadership.

If you have soldiers, Marines, airmen, or squids like that, then leaders need look to themselves for answers and make adjustments.

If that offends you as a leader, then I'm talking about you. Fix yourself.

I was one of those soldiers in the Army years ago when General Rogers started the weight program to get soldiers to look like movie stars....I had those weight-height standards hanging over my heed for almost half of my career. I worked very hard at maintaining my weight, which was a daily struggle, and just barely passed the weight-height standards on some monthly weigh-ins, but I made it to twenty years on guts and determination. I wanted to stay in and be a good soldier. I did it for me, and my stubbornness that I was as good as any of those pretty soldiers that didn't have to do anything to meet the standards. I was a senior NCO, and proud of it. I was a soldier right up to my retirement, and was proud to have served, and proud of my accomplishments. I never let the service down, even though I did not agree with the weight-height program, that expected men and woman to look like movies stars, when each soldier has a different body shape and size, but the standards were way off base. I made it to retirement, and have always respected the Army for making me that much tougher to get through the ordeal of making height-weight standards I did not agree with, but I did it, and if you have the conviction and determination you can all do it. I have no respect for quitters or slackers so git in there and finish your enlistments, and leave as respected men and women that did your service proudly. I did, and you can too. You'll never regret it.

It's one of the longest ways to a discharge. Flagged all along the way. Overweight program, extra PT sessions...etc. general discharge or less. Could take a year or longer. I personally never let a service member manipulate the system without some level of pain.

While I was booted for failing weight standards, I still got my Honorable Discharge with benefits. However before everyone blasts me, I had two medical issues that went largely unnoticed by medical. I went, but I had the bottom of the class seeing me.

1. I tore my right calf during PT and was essentially running on one leg but maintaining pace with the injured calf by pushing on the balls of my foot. The physical therapist thought it was a good idea to stretch a torn muscle. Bad idea, picture stretching pre-torn, but not completely torn paper. Torn in Summer 2011, Out in June 2012, Healed 2013.

2. I was dealing with sleep apnea and hypothyroidism. Labs confirmed it, no one had their reading glasses on. Found out 2 years after getting out.

I was willing to stick it out and finish but medical issues stopped that. The best option, finish the term and get out.

Just my opinion and nothing more, but I've always considered the height and weight standards used by the Army to be just numbers. The height weight standards Army uses at the current time and in my time are arbitrary my opinion. They do not take into consideration the level of fitness and the conditioning of the soldier.
I had two soldiers when I was in Germany. One was a fat slob, the other was the college football player that lost his scholarship due to a knee injury.
The slob got waiver after waiver after waiver so she could sure that he was losing weight he was losing fat he wasn't losing weight wasn't losing muscle mass. The football player on the other hand it's kind of hard to lose muscle mass when you're like 3% body fat. The football player wanted to stay in because he he get his college education but that didn't work out for him. Within six months he was out of the army.
The only recourse that I can see you taking just to point out that he's going to end up with a general discharge. Chances are he won't be able to get any help to the VA; he can forget about college, he can forget about the about VA medical he can forget about job assistance.
Basically you're going to have to do leadership 101 on him. That's the best advice I can give you.

Let him go.
The sad fact is that he is already a failure in life. Best to cut him loose so good troops can get on with the mission.
This has nothing to do with military service being too tough. It goes to his ability to commit to a job
or task and see it through. If you don't want a guy like this around loan him some money for his promise to repay you.

Processed him for a general discharge.

Don’t do it. That is taking the easy way out. You are establishing a way of dealing with tough situations. Embrace the suck. Finish what you started.

Attempt to convince this soldier to go out on good terms. Do his best to comply and leave the Army on good terms. Your work is cut out for you, sir.