Explore the intricacies of VPN behavior and packet loss in this informative conference talk from BSidesLV 2014. Delve into the technical aspects of OpenVPN, IPSec, and network protocols as speakers Sergey Bratus and Anna Shubina present their findings on how VPNs react to packet loss. Learn about packet timings, kernel behaviors, and the impact of algorithms like Nagle's and delayed ACK. Discover surprising insights from experiments with UDP packet dropping, IPSec fingerprints, and the effects of network queues. Gain a deeper understanding of VPN performance across various scenarios, including slow data transmission and chaining modes. Conclude with non-intuitive takeaways and potential areas for future research in this 36-minute presentation that challenges conventional wisdom about VPN operations.