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It was effectively a "distributed" license key, broken into a large number of parts and structured as a challenge-response, so that it would be difficult to answer without a full photocopy of the manual.

My favourite variant of this was F-19 Stealth Fighter asking you to do aircraft identification, which you could get from the manual .. or any library book on US warplanes.

Least favourite was some game (TMNT?) which printed the codes in gloss black on matte black.

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Microprose games had awesome manuals. Typically more than a hundred pages full of details going well beyond explaining the game itself. For example, in a flight simulator it had details on every plane in the game, the historical context of the missions, dogfighting techniques, etc...

It wouldn't be out of place in a library.

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The manual to Grand Prix 2 taught me more about car racing than any other bit of reading, video, or whatever media. It had so much about how to drive, how to use telemetry, etc.

Not that I turned that knowledge into good results but that's another topic.

What a delight that game and its manual were.

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One that comes to mind was the manuals and bits and pieces that came with Infocom text-based adventure games. They were nice bits of cruft to have alongside the actual game but in certain instances puzzles within the game could only be solved by referring to something on the card, or booklet, supplied with the game. I can't recall if it was The Hitchhiker's Guide, or Leather Goddess of Phobos, but the requirement popped up quite deep into the game.

They weren't license keys, persey, as all the printed material was the same, but a tacit test as to whether you had bought the actual game, or just copied the disk.

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Leisure Suit Larry had a twist on this where it “verified” you were an adult by asking questions that older people were much more likely to know: “During the 70s, Carroll O'Connor portrayed a…”

They were multiple choice and some of them were very tongue-in-cheek, like Richard Nixon was an “audio technician or plumber’s friend”.

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I believe there was a shortcut to skip the questions on the PC. I think it was ctrl+alt+x.
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Besides not being a one time activation, it was not a "one key". The game would ask you for "N-th word on the M-th paragraph on P-th page", at each start for example. We are talking about an age where you would not have scanners or mobile phones with cameras.
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To the adult me, this sounds tedious and not really worth. But the teen myself, I'm sure I would totally do it even I have to solve some riddle.
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>Not worth it

We live in a completely different world now. Imagine: you just bought a game, that was probably not cheap, and you won't play it because it requires opening a printed booklet you got with installation media and already have next to you? Sounds unlikely, especially since you already went through the trouble of going/driving to a physical store and installing the game (often from multiple cds/floppies, and it often took a long time). And it's not like you had a choice - another game was another drive away, and there were no refunds.

And yeah, we were younger.

Today we live in a world of constant connectivity and instant gratification. It's a better world, but a little nostalgia won't hurt

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Yeah, I did put the time in for X-Wing back in the day. A friend made copies of his disks, and let me borrow the manual so that I could copy the relevant bits down into a notebook. Took a while, but I had lots of time so not a big deal.
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for example "flashback" ask you a writen code in the manual at the beginning of each level if my memory is good. So it's was not a one time activation
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here a example of it : (I only remember the first version) https://www.reddit.com/r/dosgaming/comments/86yxp4/question_...
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It wasn't individual per install. Anyone with the game manual could find the word or code in the book. Some games asked for a random word from the manual on boot, so you couldn't just share the code, you needed to share the entire manual (or decompile or something to find all the words it is looking for).
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And the manuals usually themselves had "copy protection". Many were printed in variations of dark colours, such that any easily accessible copier would just copy a black page.
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this was the comment i was looking for! i remember those red pages and found them annoying on even legitimately purchased games (which is how copy protection has always been IME - makes it so legitimate purchasers of a game got annoyed and hence, got cracks for games to just not be as annoyed!)
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Yes because the license key was easy to write down on a sticky note and provide it with the copied floppy disk. With this mechanism you either needed to have a copy of the entire manual, or at least all the answers to the questions it would ask.
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I remember one of the later Wizardry games (I believe it was Return of Werdna) came with a pamphlet full of codes that was printed on very dark brown paper that made it very difficult to make legible photocopies.
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