It was back in 1997 at my first job out of college. I was a networking stack engineer on the Netscape Browser. At that time, the email client, news reader, and browser were essentially rolled into one (I'm sure I'm pissing some lawyer off by making that statement as they'd inevitably argued in court somewhere/sometime that they were separate; hell, I was probably a witness in a case making the argument at some point), anyway.
I got an email intro from someone on the Mail team introducing me to an FBI agent. I was a kid (24 or so) and I was intrigued. The agent was looking for some help navigating the underlying Mail db on a computer they'd recovered in a child-porn raid. While he obviously didn't disclose much, he explained to me that they'd spent years watching this guy and tracking his non-digital activity. He explained to me how he'd dedicated his career to nailing this guy, yet he'd hit a wall with the digital stuff he *knew* was there. I sympathized deeply. Child-porn? Horrible! Dedicated career to stopping this guy? How do I help?!? I was in!
They had one team working on the binary image attachments, but they were having trouble understanding and mapping Mail's underlying message/meta-data database (berkeley db) to/from them. He couldn't send me anything to actually work on (child porn stuff apparently can't move across state lines/wires... even if/when law enforcement is doing it), so it was like doing remote surgery trying to help him out. After several hours of helping, my day-job work was starting to pile up and I had to stop and ask myself how I was supposed to prioritize this apparently very high priority thing. How was I supposed to stack rank this against my companies' commercial needs? I was essentially volunteering my time. Would my company get any recognition for this? Should it? I was 24... what the hell did I know?
The agent started leaning on me more and more for more and more help. My work responsibilities started slipping so I consulted my boss. He left the ball in my court, empathizing with the situation. He wanted me getting my day-job done, but also wanted to help in what appeared to be a big deal.
I helped off and on for another couple of weeks, but at some point I realized we'd done 80% of the work that could be done without me going full-time on the project and co-locating with him so I could sit with the actual meta-data. I told him I had to get back to my day-job and that I was sorry. He expressed great appreciation for all the help, and also disclosed to me in the processes how outgunned he and his department were in this "digital age." When we broke off all the interaction it left me feeling really scared actually. There I was, a kid, coming to the realization that this thing that was supposed to protect me, my government, wasn't able to do so. It hit me like a ton of bricks. A corporate entity, me/my-company in this case, was, in his eyes, required to help them catch a horrible criminal. Leaving the project was really hard.
He left me enough bread crumbs that I was able to piece together a massive, publicized, multi-state, child-porn ring bust (biggest to-date at that time), was the one that I'd contributed to. Assuming everyone involved in that was indeed guilty, I'm proud of the work I did.
A couple of years later during some patent litigation case, I was again confronted with the fact that my government (USPTO in this case) had been leapfrogged by technology. The USPTO crumbled before my eyes as I watched patent agents fumble through software patents and a case they really didn't understand (all the way up to the presiding Judge). I left that experience faithless in the systems's ability to manage the patent concept across software.
Several months after working on the mail db project, I received a FBI mug in the mail at work. No return address, and no note inside (I later found out the FBI can't pay for assists like this with $ or gifts). It's my favorite mug. It represents so much.