In 1905, the Spanish philosopher George Santayana famously wrote the line "Those who cannot remember the past are condemned to repeat it." Nothing can escape this inevitability: like death and taxes, we have all looked at our screens in bewilderment at an HTTP 200 OK response that contains text in the body reading "er, actually this is an error", or marveled at pagination design that creates an infinite loop for you to consume. How did we get here? In this session, I will be meandering through history, real examples, and anecdotes. The internet is littered with a graveyard of poorly designed APIs. Instead of launching yourself head-first into this murky world of quirks, maybe take a moment to learn the history of APIs and their mistakes so you don't repeat them.