All communication leaves the possibility for crossed wires. And as we become more connected, there’s a chance for those with ill intentions to steal our information and meddle in our daily lives—with devastating results. Smriti Bhatt breaks down the complexity behind machine-in-the-middle attacks. Johannes Ullrich tells us why we shouldn’t always trust that free WiFi. And the “father of SSL” Taher Elgamal notes that while cryptography can address the increasingly sophisticated nature of malware, there are no safe bets in security.