Thanks for the story, lots of good memories like that too. I used to always try to call boards named things like Thieves Guild, Pirates Cove, or some sort of 31337 sounding name in the hopes of discovering some new scene or underground board. The best boards were dedicated 100% and didn't even try to fake it, but did a lot of the stuff I listed below.

Regarding boards with fake or legit parts, I used to routinely page sysops on boards I thought were underground or had hidden parts. The classic ones later on were almost always based on PCBoard and later Ami/X, but highly customized. The early ones generally just ran on whatever the best software was at the time and boasted about the hardware. They'd have all sorts of legit content typically and even legit users, but so much of it was a joke. I used to call one board that was big with HAM radio people and early Internet adopters. The most nerdy discussions you can imagine. What they didn't know is that there was a second part of the board that had a huge ROM dump, Amiga, C64, and PC warez scene.

As far as sysops go, I will also admit to spying on my users as sysop and as a co-sysop on various boards. I sometimes would break people into chat and kick them off. There were also many plug-ins that initiated fake chats and logged the results. A particular one that I'll never forget on one board I was co-sysop on featured an ANSImation (animated Ansi) by JED of ACID with some troll I think flipping you the bird as it brought up chat. Sometimes we'd post the fake chats for other users for comedy purposes.

I was nice and would help people find files, talk about fun stuff, meet in person, but I was also a dictator and would boot anyone on short notice. There were often periods of paranoia from alleged "busts," most of which probably never happened though I know for sure some did. Lots of calling people NARCs and so on.

One of the funniest things I used to see people do was upload fake files. Early on it was random binary or generated text files. Later it was things like blank audio or the same pictures renamed and zip'd. They were just so desperate for upload credit and time that they'd do this insane stuff. Checking files was really a pain. Thankfully on my boards, we were snobs about content, like on the warez boards we'd think we were so cool having 0-30 day, then it was something like 0-14, then 0 day stuff. So stupid banning and deleting people for uploading something 2 months old. Same thing happened on various FTP dumps that started to displace BBSs for file purposes later on.

Anyway, BBSs and the relationship to various underground scenes was a funny thing. On the one hand, a lot of the communities could be very exclusive and created all sorts of protections, barriers, precautions, and more. On the other hand, they'd then make it super obvious what they were up to in so many ways.
Classic examples include:

- Advertising your BBS on other not-so-secret boards

- Commissioning ANSI art from a group like ACID, ICE, etc. with the name in the ANSI and often the area code too. Not uncommon to see things like +1-212-YOU-WISH Sysop: Mr Man. Awesome, now I know the name and what area code to look for the number at least, if not people who run it.

- Logon screen with ANSI depicting group affiliations. THG Eastern HQ = Genesis Distro = Legion of Doom HQ. It was hilarious because even if you didn't have access, you instantly knew you called a pirate board, cracking board, art board, whatever.

- New User Application filled with terminology from whatever scene. Again, same as the previous item.

- New User Password. As if most BBSs without anything illegal would have this.

- Users with huge ratios listed. Hmm, not many files on this BBS and yet this guy uploaded 500 megs!

- Certain BBS Software. You could be pretty sure that someone running things like Ami/X were into warez, Oblivion, Iniquity, Eternity, etc. - art, and so on. The more customized with nice ANSI too, usually the more likely it was underground. Huge tip-off the board was legit if it ran something like WWIV, Wildcat!, Celerity, and a few others we all considered hugely lame. Renegade and other Telegard or Forum hacks always made you wonder on the other hand. The old stuff on Atari ST, C64 etc was harder since there was a huge deluge of stuff and not as many ones that were 100% preferred yet.

We thought we were pretty cool in those times, but wow I look back at some of it and cringe. Good times and I was lucky enough to be involved in most underground scenes, while still getting time to interact in the legit scenes too.