Software glitches like the Y2K bug and its recent echoes, such as the New York City parking meter failure serve to remind us of the complacency that often settles into organizational culture, and which allows security threats to turn into full-on failures. The New York City parking meter failure was soon eclipsed by the enormity of the COVID-19 pandemic, which has occupied the world’s attention ever since. But this story should not be forgotten, because it has roots that extend far back into the past and – more importantly – has serious implications for computing and threat management far into the future. It starts with some parking meters in New York City. And it teaches us a lot about complacency