For instance, the 2003 California Driver's Handbook[1] first introduced the concept of "bike lanes" to driver education, but contains the advice "You may park in the bike lane unless signs say “NO PARKING.”" which is now illegal. Anyone who took their test in the early 2000s is likely unaware that changed.
It also lacks any instruction whatsoever on common modern roadway features like roundabouts or shark teeth yield lines, but we still consider drivers who only ever studied this book over 20 years ago to be qualified on modern roads.
1. https://dn720706.ca.archive.org/0/items/B-001-001-944/B-001-...