On 22 October 2137 BC, a solar eclipse passed over China without warning. Two royal astronomers, Hsi and Ho, allegedly failed to predict it, and according to ancient texts, were executed for their negligence. Modern astronomical calculations confirm the eclipse occurred on this date, making it one of the earliest documented celestial events in human history. This episode also explores the War of Jenkins’ Ear, which began in October 1739 after a British sea captain presented his severed ear to Parliament as evidence of Spanish aggression, and André-Jacques Garnerin’s pioneering parachute jump from a hydrogen balloon over Paris in 1797. We close with a small asteroid detected and tracked before it entered Earth’s atmosphere over the Pacific in October 2024, the tenth such object to be spotted in advance. From ancient China to modern telescopes, humans have been watching the sky, sometimes successfully, sometimes not, but always with the understanding that it matters.