What is the most difficult ethical decision you were faced with in the military?

I had Corpsman who caused a negligent discharge. He was awesome medically, we needed him, and an NJP on his record probably would have ended his Career. We decided we had to do the right thing, brought him up to regimental NJP. The Colonel considered all the evidence, the Corpsman pled guilty, the Colonel found him not guilty. Sometimes faith in the system and doing the right thing pays off.

Had a Supply Sgt ship a box of classified hard drives (they didn't have anything on them, but they were controlled) via UPS from one coast to the other.

Had to report it. Potential Career ender. Potential jail time.

A week later the SSgt I worked for asked me "Did anyone ever train him?" and that "Oh..#^^ moment" hit. Called the LtCol that was doing the investigation, asked to speak to him. Went to his office, and sat down for 5 minutes, and said "Sir, I don't think we as an organization ever taught him the right way."

The Sgt was wrong. Absolutely wrong. In "theory" should have known better. but the instant it happened, it had to go up the chain, and I couldn't ask him about it. Couldn't talk to him about an open investigation. Had my SSgt not said something, he likely would have been fried. I don't know if my talking to the investigator changed anything or not, but I know he ended up with an "informal" Letter or Reprimand (gone when he left the Unit).

I had a female E-7 who probably should have been MED Boarded and non deployable, but she asked for a meeting with me to discuss this matter with me. She was very hard working and had a Masters Degree. She served 18 years and told me (my words) that she ran a marathon and wanted to hit the finish line. In situations like this I look at balancing what is best for the soldier vs. what is best for the Army. My 1SG and I found a non deployable slot so she can finish out.