It's been said that we don't really understand a system until we understand how it fails. Despite having written a (toy) TCP implementation in college and then working for several years in industry, I'm continuing to learn more deeply how TCP works — and how it fails. What's been most surprising is how basic some of these failures are. They're not at all obscure. I'm presenting them here as puzzlers, in the fashion of Car Talk and the old Java puzzlers. Like the best of those puzzlers, these are questions that are very simple to articulate, but the solutions are often surprising. And rather than focusing on arcane details, they hopefully elucidate some deep principles about how TCP works.