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Explore trust agility in this 20-minute conference talk from USENIX Security '25, examining how to navigate the rapidly evolving TLS trust and Web PKI ecosystems. Learn about the foundational shifts occurring in root programs, including stricter policies that will limit root certificate lifetimes to 10 years and server certificates to maximum 47-day validity periods by 2029. Understand the operational and security challenges these crypto-agility promoting changes create across different environments. Discover the practical concept of trust agility - the capability to securely and rapidly update trust relationships as cryptographic standards, certificate authorities, and threat models evolve. Examine the disparities between quick browser updates and slower consumer device upgrade cycles, particularly in developing countries, while addressing machine-to-machine communication and non-browser use cases that fall outside traditional browser-based trust models. Gain insights from real-world experience on strategies for achieving trust agility through automation and lifecycle-aware certificate management across diverse endpoints. Acquire concrete techniques for navigating the modern TLS trust landscape and future-proofing PKI infrastructure in an era of transient digital relationships.