It's funny to think how much effort was put into preventing bootlegging, when now everything is being recorded all the time.
The few bands that didn't care or even encouraged it reaped the benefits. I was a huge Ween fan in the 90s and bootlegged a show of theirs myself. Camera and recording devices were allowed and the result was a tremendous amount of live content available online. For some bands this might not matter, but they rarely played the same set list twice and often played songs differently from show to show. In the early internet days, there was more ween content online than you could ever hope to listen to.
Effort is still being put into it. Just this weekend YouTube put the 4K Coachella streams behind SABR. I could still get 1080p easily but 4K required some fanangling.
As a student in the 90s I worked security for the student concert group on campus. We had to frisk people for Jello Briafa (Dead Kennedys) spoken word performance. I found a couple of tape decks, but those were allowed.
They still put a lot of effort sometimes. I saw Dave Chapelle in NYC and they made us put our phones in these pouches which were unsealed on exiting the show.