Explore the complexities of software security and trust chains in this 46-minute conference talk from Circle City Con 2015. Delve into the Open Crypto Audit Project and examine the intricacies of the Internet Core Trust Chain. Investigate the challenges of basic server certificate deployment and network transport integrity. Learn about the OpenSSL Audit and its implications for software security. Gain valuable insights into emerging trends and receive cautionary advice for navigating the complex landscape of digital trust and security.