When I first started with the company, we would pay the software company a licensing fee for every site we ran the point-of-sale software on, usually to the tune of about $1000 a year.
A bit of background: My boss has the technical expertise of a field mouse. I learned quite early that the software we were using had NO safeguards against piracy at all, and we could easily rob the software company blind if we so chose. I never let my boss know that, but apparently he figured it out on his own, as he went through AT LEAST 5 years without paying the annual licensing fee on any of the new sites.
Sometime around 2010, I get sent an email with a survey from the software vendor. Not knowing that my boss was ripping them off of $25,000/yr in licensing fees, I gave full and complete answers. 60 sites, complete with how long we had been using the software at each site, etc. etc. etc.
Needless to say, they weren't happy with finding out that my boss had essentially ripped them off of well over $100k in licensing fees. He comes into my office and worryingly asks what kind of information I gave them. You could see his heart sinking as I replied.
I told him straight out...."Hey look. Paying for this stuff is above my pay grade. It's my job to install the software, configure it, and train the staff. The rest is on you." He knew he was pretty much fucked.
(Side note: I'm sure some are surprised that he didn't try to dump it on me to save his own ass, but he was smart enough to realize that I had more than enough information to sink him even harder had he tried to.)
I recall the day the representative showed up to the office for a meeting. I was not privy to the actual meeting itself, but when he came out he was very happy to report that the vendor was willing to settle for $150,000. His tone of voice indicated that he was very grateful to have kept his job and not be sued into oblivion in the process.
Side note: This was only the first time the man had pulled a stunt like this. About a year later, he was "questioned" by the state regarding some paperwork that contained what could best be described as "fuzzy math". The only way he wiggled his way out of that is because while state auditors had their suspicions, there was nothing concrete they could nail the guy with.
I am now in charge of all software for our main district. Not so much as wallpaper can be added without my say-so, and I spent the better part of 5 years developing relationships with all the right people; while the auditors still give us the stink-eye from time to time, I've at least gotten them to the point where they're willing to take my answers at face value.