Technical guides, insights, and news from the Tailwind engineering team.
Three civilian agency sites rotated this week from long-validity DigiCert leaves to fresh 198-day DigiCert leaves — the first wave of federal civilian sites in the dataset to step off the pre-SC-081v3 long-validity cohort and land cleanly under the 200-day cap.
Bill Church 
Issue 0 surfaced one civilian agency with an expired apex cert and a healthy www. This addendum extends the methodology to the full inventory: 28 of 109 entities (26 percent) run two cert programs on one domain, concentrated in civilian agencies and absent from the defense industrial base.
Bill Church 
A new recurring series tracking what the CA/Browser Forum SC-081v3 validity reductions, the dismantling of OCSP, and post-quantum handshake adoption actually look like in the federal public web. Issue 0 establishes methodology and presents the 2026-05-03 baseline.
Bill Church 
TLS 1.3 encrypts client certificates during the handshake, hiding identity from passive observers, but breaking traditional network monitoring.
Bill Church 
Semantic caching enables LLMs to serve cached responses for semantically similar queries by converting text to vector embeddings and matching based on meaning rather than exact text.
Bill Church 
LLMs are sophisticated pattern-matching systems like parrots mimicking speech, not true problem-solvers like crows. They lack genuine comprehension, causal reasoning, and intentionality despite their impressive capabilities.
Bill Church 
NIST's new data protection guidance highlights WebAssembly as a versatile security tool for cloud-native applications, complementing eBPF's kernel-level capabilities.
Bill Church 
Let's Encrypt's decision to end OCSP support by August 2025 raises concerns about certificate revocation in government and high-security environments where real-time validation is mission-critical.
Bill Church 
A humorous exploration of automation failures using a car's windshield wipers soaking the author as a metaphor for understanding risks in complex technical systems and AI agents.
Bill Church 
White House revocation of AI security executive orders creates regulatory vacuum. Organizations must strengthen internal AI security measures as Project Stargate's $600B investment accelerates development without standardized protocols.
Bill Church 
The Treasury breach attributed to Chinese state-sponsored actors exploited vendor access, compromising 419 computers. Organizations must strengthen third-party risk management to prevent similar incidents.
Bill Church 
An IT professional discovers observability lessons while living in an RV after a flood, comparing RV tank monitoring to application infrastructure challenges.
Bill Church 
The Treasury Department cybersecurity breach reveals critical vulnerabilities in credential management. Learn practical security measures including ephemeral authentication and just-in-time access controls.
Bill Church 
Geoffrey Hinton raises AI existential risk estimates to 10-20% over three decades. Recent military incidents highlight critical need for human oversight in AI weapons systems.
Bill Church 
Tech leaders must prioritize digital accessibility beyond compliance. The European Accessibility Act deadline in June 2025 presents an opportunity to build inclusive products using WCAG 2.1 standards and automation tools.
Bill Church 
A cautionary tale about how misinformation spreads rapidly on social media, using a viral scare about toxic black plastic utensils as an example, and offering practical guidance on verifying information before sharing.
Bill Church 
Strategies for designing resilient systems and swift recovery from incidents like the CrowdStrike outage, emphasizing automation, PXE booting, and business continuity planning.
Bill Church 