Have you been involved in a situation where you had to confront a superior about their conduct?

My first assignment as a Navy Chaplain was at a training center. We were at a military ball one year and in opening the ceremonies the MC asked all the designated drivers to stand. I watched my CO and XO stand up while both had bottles of beer sitting in front of them. I kept an eye on them the remainder of the night and that was the only drink that either of them had and we left 4 hours later, so I didn't say anything that night. I did however go to the XO on Monday morning and tell him what I had seen and pointed out that the command table was surrounded by student tables. Most of these students were under 21 and we hammered them all the time about not drinking underage and responsible drinking once you were of age. He hung his said and said, "Oh my gosh, I didn't even think of that. You're absolutely right Chaps. We have to set the example. I'll talk the to Skipper." Turned out well. The key is to approach it with humility and tact, and not to lord it over the superior even if you feel they are in the wrong.

I was very lucky, we either didn't see or know about any such problems, or they were good enough leaders to not do anything stupid.

I read the question and most of the responses. What mystifies me is that our military has devolved to the point to where a subordinate can or is encouraged to challenge a senior. What happened to following orders and doing what you are told? When did it become okay to question authority? Like many of you, I have had my share of less than stellar leaders but as the subordinate, it wasn't my place to "correct" them. That is the responsibility of their senior. In my opinion, our military was much stronger when rank really was "everything." In the Navy, a Chief Petty Officer trains junior Officers and that is a matter of tradition. An E-6 (or below) challenging a Chief or above, will and should get shut down real damn quick. Stay in your paygrade, Shipmate!

Only once - as a Captain, & company commander, had to remind an moderately intoxicated LTC that his language was a might racy for the ladies attending a Bde social function. Following the event, and incident, we became staunch friends as much as a Bn LTC and a Captain can be. A little tact, some careful wording, and a few words of caution and the incident was rendered mute and no one was humiliated.

While stationed at Loring AFB Maine in 1986 my reporting official a 1st Lt was attempting to sell a MSgt in my office home made pornography. Videos and still photos. I was a TSgt at the time. I thought about what was happening and knew it was a violation of the UCMJ. I informed the Lt that she was in violation of the UCMJ and was under apprehension. I then instructed an A1C in the office to contact the Security Police and to call our Lt Col office chief immediately. The Lt told me I couldn't do this and I informed her that she would remain seated and await the arrival of the Col. and the SP's. The disposition, The Lt was court martialed and given a dishonorable discharge along with several other officers who were part of her porn ring.

many of times and it got resolved.

Had a Captain strike up a relationship with a MSG in the same unit while in Iraq... after previously being involved with a SSG and before that an E-5. Guess he was trying to climb the rank ladder.
Anyway, his conduct was well known and the company commander did nothing about it.
One day I came back to the FOB from the COP I lived on and caught the MSG's roommate (a PFC, but quarters were tight for females) sitting outside at 2am. I just said hello at first, then I realized what was going on and decided to post up outside for the night and wait them out. They outlasted me though as I had to go to a meeting at 0800.
Later, I was in my secure shack late one night writing reports to post on the SIPR side, when I heard noises in the adjacent room. Irate, I pounded on the wall and got a threat from the other side. "No worries, sir. I'll come to you." and hustled to the other door. They hurried up and locked it, so I resolved to post up outside again... this time with nothing but time on my hands.
I spent the whole night throwing rocks at the side of their plywood walls - just to let them know I cared. Eventually I had to take a piss and they took the opportunity to slip away. But this time I'd had enough and found the commander to wake him up to fix this. He acted as though he had no idea, but I've been doing this CA thing for a minute and know deception when I see it. He got around to telling me that he'd heard "rumors" and told him to stop... but I rather doubt the truth of that too.
Making matters worse, the CO had recommended both CPT Fraternization and MSG Easy for MSMs, much to the consternation of those of us actually out in the field actually doing the work.
The peasants started to revolt.
At the end of the day, the CO did nothing and the two fraternizers got married later, all the while denying that they'd had a relationship.
They weren't that sneaky though, as one day the female (now a 1SG) got posted on the USACAPOC home page sporting her new last name...
I called up the officer involved, and just told him to log in.
"Nice OPSEC, sir."

As a Military Policeman I often found myself dealing with persons of superior rank. As long as I maintained a professional demeanor I never had an instance when their rank became an issue except for highly intoxicated individuals who had compromised their rank with their unprofessional and usually illegal behavior. I always attempted to do my job professionally and stayed away from belligerent and demeaning comments unless they continued in that vain. Most responded in kind and those that didn't set the tone of the exchange and were invariably humbled by the outcome.

FROM THE IG DESK: As a Lieutenant Colonel, I held the second position of "Deputy Inspector General" for our 3-State Regional Support Command. Our O-6 Colonel "Detailed IG" was relieved of his position due to allegations of sexual harassment... absolutely stunning to all concerned. Our office files are highly confidential and protected in equal measure to any attorney-client privilege and I was instructed by our two-star not permit him entry into our office while the investigation was in process. You guessed it...he came strolling in the following morning as if nothing had happened. The proverbial pin was waiting to drop and dead silence gripped the entire office staff with hard tension as I stood at the gates to confront him. For an instant, I was frozen; faced with the realization I had to challenge my superior under the locked gaze of half a dozen office staff staggered to mute staring. Girding myself with as much tact as I could muster, I politely informed him I could not permit him to enter the office as, "Major General...... " was clear in his instruction and if you have any question I must ask that you please see him for edification." He muttered a profanity under his breath and left, to the relief of all staff present. The allegations against him were substantiated, he received a "Relief For Cause" OER under AR 623-3, removed from his position and fired. I was promoted into the position of "Detailed IG" as a result. I want everyone out there to understand this is NOT the way I would ever have chosen for personal advancement. Allow me a moment to share with all our military Readers the following: I graduated from the Inspector General Academy in Washington, D.C.. During the course of that instruction, a great deal of historical statistics were shared. The largest categories of Command failure across the entire military board of all services were "Sex" and "Money." Those two reasons ruined more careers than any other statistical event documented. Be advised. JCH

Yes I've dealt with it. More than once. Retaliation seems to be something you could set a clock to.

The military is a go along to get along place. I think anyone, with some time in, could say that it's not making for a better military.