Working Model, a physics simulator for the 68K Mac, did that. "Enter the last word on page NNN". For one release, the manual got some minor modification just before printing, changing the pagination of the last chapters. If the page number was in the first 3/4 of the book, it worked, but if in the last quarter, it didn't. Paying customers very annoyed.
One was the colour chart supplied with Jet Set Willy (http://steveremembers.tumblr.com/post/90840692306/the-jet-se...). When the game started it gave you a location on the chart and you had to type in the colour. It was difficult at that time to make colour photocopies.
The second was the Lenslok (https://en.wikipedia.org/wiki/Lenslok http://birdsanctuary.co.uk/lenslok/) which was an absolutely atrocious system - more information in the Wikipedia article.
It's crucial that Dungeon Master was an excellent game[0] because otherwise, players might have simply decided it wasn't worth their time or money.
[0]https://en.wikipedia.org/wiki/Dungeon_Master_%28video_game%2...