Safeguarding Internet Trust: From Reactive to Continuous 

Leave a reply

The internet rests on a foundation of core infrastructure components that make global communication possible. Among these load-bearing elements are DNS, DNSSEC, BGP, BGPsec, WebPKI, RPKI, transparency logs, IXPs, Autonomous Systems, and various registries. This includes critical governance bodies like ICANN and IANA, standards bodies like the CA/Browser Forum. These systems don’t just enable the internet – they are the internet, forming the critical backbone that allows us to establish secure connections, route traffic reliably, and maintain operational trust across the global network.

The PKI and transparency mechanisms that support these systems, particularly WebPKI, RPKI, and Certificate Transparency, are especially critical load-bearing elements essential to delivering the internet’s net value. When these foundational elements fail, they don’t just impact individual services – they can undermine the security and reliability of the entire internet infrastructure and erode the fundamental trust that billions of users and organizations place in the internet. This trust, once damaged, is difficult to rebuild and can have lasting consequences for how people interact with and rely upon digital services.

This foundational role makes the governance of root programs, which oversee these trust systems, absolutely critical. Yet recent incidents and historical patterns suggest we need to improve how we approach their governance. While no root program is perfect, and some have made significant strides in adopting product-focused practices and proactive risk management, there remains substantial room for improvement across the ecosystem. This framework isn’t meant to dismiss current efforts, but rather to synthesize best practices and push the conversation forward about how we can collectively strengthen these critical trust anchors.

To transform root programs from reactive administrative functions into proactive product-driven systems, we need a clear framework for change. This starts with defining our core mission, establishing a vision for the future state we want to achieve, and outlining the strategic pillars that will get us there.

Mission

To safeguard global trust in internet infrastructure by managing systemic risks, driving technical innovation, fostering transparent governance, and building durable systems that serve generations to come.

Vision

A resilient and adaptive trust ecosystem where:

  • Governance is proactive and risk-aware, balancing technical rigor with user-centric principles
  • Infrastructure and processes are continuously validated, transparent, and simplified
  • Collaboration fosters innovation to address emerging challenges and deliver long-term security

Strategy

1. Transparency and Accountability

  • Establish robust public verifiability for all CA operations, leveraging tools like transparency logs and continuous compliance monitoring
  • Communicate decisions on inclusion, removal, reentry, and policy changes openly, ensuring stakeholder trust
  • Build mechanisms for regular stakeholder feedback and confidence measurement, ensuring the ecosystem remains responsive to both technical and user needs

2. Integrated Risk Management

  • Apply blast radius management to minimize the impact of failures, for example by segmenting trust dependencies and ensuring risks remain contained
  • Use real-time monitoring and automated enforcement to detect and mitigate systemic risks
  • Implement standardized processes for risk assessment and mitigation

3. Proactive Governance

  • Shift from reactive to anticipatory governance by identifying potential risks and implementing early countermeasures
  • Leverage automated monitoring and enforcement to prevent and catch issues before they become incidents
  • Maintain clear lifecycle management processes for all ecosystem participants

4. Modernization and Simplification

  • Establish WebPKI governance primacy for included roots and minimize cross-ecosystem trust relationships
  • Limit what each CA is trusted for, reducing complexity and narrowing the scope of potential failures
  • Employ these measures as part of broader blast radius management strategies

5. Collaborative Ecosystem Building

  • Support and fund foundational open-source projects and critical infrastructure that the ecosystem depends on
  • Implement shared accountability mechanisms, ensuring all ecosystem participants bear responsibility for maintaining trust and integrity
  • Encourage CAs to align their policies not only with their own standards but also with aggregated internet governance policies, and best practices, especially for global use cases like TLS
  • Partner with browsers, CAs, and researchers to co-develop solutions for current and emerging threats
  • Foster an environment of mutual respect and constructive partnership

6. Commitment to Continuous Improvement

  • Drive decisions through data collection, measurement, and empirical analysis
  • Evolve policies based on quantitative feedback, incident analyses, and advancements in technology
  • Regularly reassess and refine program criteria to remain relevant and effective
  • Maintain clear processes for managing organizational transitions

The Stakes Are Higher Than Ever

The history of CA failures tells a sobering story – major CA distrust events occur on average every 1.23 years, each one threatening the foundation of trust that enables secure internet communication. These aren’t isolated incidents but rather represent recurring patterns of systemic failures in CA operations and governance.

Consider the range of critical failures we’ve seen: From DigiNotar’s complete infrastructure compromise in 2011 leading to rogue Google certificates to TURKTRUST’s “accidental” intermediate certificates in 2013, to government-affiliated CAs repeatedly undermining trust through deliberate actions or “accidents.” Take for example the ICP-Brasil case, where a root that had announced the end of SSL issuance continued to issue certificates months later – demonstrating how root programs’ decisions (or lack thereof) to maintain trust in roots that should no longer be part of the WebPKI can create unnecessary risks.

These incidents follow disturbingly consistent patterns:

  • Security breaches and infrastructure compromises that enable unauthorized certificate issuance
  • Systematic misissuance of certificates that undermine the entire trust model
  • Poor incident response handling that compounds initial failures
  • Non-compliance with industry standards despite clear requirements
  • Operational vulnerabilities that go unaddressed until it’s too late
  • Deceptive actions that breach the fundamental trust of the ecosystem

The Economic Reality

The current ecosystem suffers from fundamentally misaligned incentives. Root programs are typically run by browser vendors as a necessary cost of doing business, often competing with commercial priorities for resources and attention. Meanwhile, CAs face strong pressure to maintain their trusted status but weak incentives to uphold rigorous security practices. When security failures occur, users bear the cost while CAs often face minimal consequences. This economic reality is compounded by an ineffective auditing system where CAs select and pay their own auditors – reminiscent of the dynamics that enabled financial scandals like Wirecard and Enron.

The Long Tail Problem

A particularly concerning aspect of the current system is the “long tail” of rarely-used CAs. Many root certificates in browser trust stores belong to CAs that issue only dozens to hundreds of certificates annually, yet they maintain the same broad trust as major CAs issuing millions. These low-volume CAs pose risks that far outweigh their utility, creating unnecessary attack surfaces in our trust infrastructure. Regular assessment of each CA’s ongoing value to the ecosystem, balanced against their inherent risks, should inform continued inclusion in trust stores. This approach ensures the ecosystem maintains an appropriate balance between accessibility and security.

The Product-Centric Approach

To address these challenges, root programs must evolve from administrative oversight roles to become proactive, risk-managed entities. Here’s how a product-centric framework can transform root program governance:

1. Transparency and Accountability

  • Implement robust public verifiability for all CA operations
  • Leverage transparency logs and continuous compliance monitoring
  • Ensure open communication about inclusion, removal, and policy changes
  • Require automated reporting of security incidents and operational compliance

2. Blast Radius Management

  • Segment trust dependencies to contain potential failures
  • Implement dedicated hierarchies for specific use cases
  • Limit CA trust scope to reduce complexity and narrow failure impacts
  • Deploy real-time monitoring and automated enforcement

3. Risk-Based Governance

  • Move from reactive to anticipatory governance
  • Apply different levels of scrutiny based on CA context and risk profile
  • Regularly assess whether each CA’s utility justifies its risks
  • Implement meaningful technical restrictions on certificate issuance

4. Modernization and Simplification

  • Establish and maintain WebPKI governance primacy
  • Implement dedicated hierarchies for specific use cases
  • Limit CA trust scope to reduce complexity and narrow failure impacts
  • Deploy real-time monitoring and automated enforcement

5. Shared Accountability

  • Support and fund critical infrastructure and monitoring
  • Foster collaboration between browsers, CAs, and researchers
  • Establish clear responsibilities across all ecosystem participants
  • Create incentives that align with security goals
  • Balance rigorous oversight with constructive partnership
  • Develop clear processes for managing CA transitions and lifecycle events

Measuring Success

Like any product, root programs need clear metrics for success:

1. Risk Reduction

  • Track mis-issuance rates and time-to-remediate
  • Measure decrease in systemic vulnerabilities
  • Monitor adoption of proactive security measures
  • Track stakeholder confidence through regular surveys

2. Ecosystem Resistance

  • Assess recovery capabilities from disruptions
  • Track implementation and effectiveness of blast radius containment measures
  • Monitor CA inclusion, removal, and reentry success rates

3. Operational Excellence

  • Monitor CA inclusion and removal process efficiency
  • Track adoption of modern security and governance practices
  • Measure response times to security incidents and evaluate the thoroughness of incident handling
  • Evaluate lifecycle management process consistency and post-incident improvements

Lifecycle Excellence

The sustainability of root programs depends on having clear, repeatable processes for managing the complete lifecycle of CAs – from inclusion to potential removal. This includes:

  • Standardized onboarding and transition procedures
  • Regular assessment checkpoints
  • Clear criteria for maintaining trusted status
  • Efficient processes for handling CA turnover
  • Proactive planning for ecosystem evolution

The Trust Paradox

One of the most challenging aspects of root program governance is the inherent contradiction between trust and security. As we’ve seen with government-affiliated CAs and others, institutional incentives often directly conflict with security goals. A product-centric approach helps address this by:

  • Implementing consistent risk evaluation frameworks that account for different institutional incentives and constraints
  • Requiring proactive enforcement rather than post-incident reactions
  • Creating clear, measurable criteria for ongoing trust
  • Establishing automated compliance checks and monitoring
  • Establishing feedback loops between governance bodies, CAs, and end-users to maintain alignment

The Path Forward

Root programs must continue evolving beyond reactive governance and inconsistent enforcement. By adopting a product mindset that emphasizes continuous improvement, measurable outcomes, and proactive risk management, we can build an even more resilient trust ecosystem.

Immediate actions should include:

  • Implementing automated compliance monitoring
  • Establishing clear criteria for CA risk assessment
  • Developing robust blast radius management strategies
  • Creating transparent processes for trust decisions
  • Supporting proper funding for monitoring infrastructure
  • Implementing standardized CA lifecycle management processes
  • Building collaborative frameworks that balance accountability with mutual trust

Conclusion

The security of the internet depends on root programs functioning effectively. By treating them as products rather than administrative functions, we can build a more secure, transparent, and reliable trust ecosystem. This transformation won’t be easy, but the cost of maintaining the status quo – as evidenced by the long history of failures – is simply too high.

The question isn’t whether we need root programs – we absolutely do. The question is how we can continue evolving them to meet the security challenges of today’s internet. A product-centric approach, focused on proactive risk management and measurable outcomes, offers our best path forward.

Beyond Memorization: Preparing Kids to Thrive in a World of Endless Information

Leave a reply

What does it take to prepare our children for a tomorrow where AI shapes how they get information, robots change traditional jobs, and careers transform faster than ever—a time when what they can memorize matters far less than how quickly they can think, adapt, and create? As a parent with children aged 29, 18, and 9, I can’t help wondering how to best prepare each of them. My oldest may have already found his way, but how do I ensure my younger two can succeed in a world so different from the one their brother entered just a few years before?

We’ve faced big changes like this before—moments that completely changed how we work and what opportunities exist. A century ago, Ford’s assembly line wasn’t just about making cars faster; it changed what skills workers needed and how companies treated employees. Decades later, Japan’s quality movement showed us that constant improvement and efficient thinking could transform entire industries. Each era required us to learn not just new facts, but new ways of thinking.

Today’s change, driven by artificial intelligence and robotics, is similar. AI will handle basic knowledge tasks at scale, and robots will take care of repetitive physical work. This means humans need to focus on higher-level skills: making sense of complex situations, evaluating information critically, combining ideas creatively, and breaking down big problems into solvable pieces. Instead of memorizing facts like a living library, our children need to know how to judge if information is trustworthy and connect ideas that might not seem related at first glance. They need to see knowledge not as something you collect and keep, but as something that grows and changes through questioning, discussion, and discovery.

Where can we find a guide for developing these new thinking skills? Interestingly, one already exists in our schools: the teaching strategies developed for gifted and twice-exceptional (2e) learners—students who are intellectually gifted but may also face learning challenges.

Gifted and 2e children think and learn in ways that are often intense, complex, and different from traditional methods. Teachers who work with these learners have refined approaches that develop multimodal thinking (using different ways to learn and understand), metacognition (thinking about how we think), and critical evaluation—exactly the skills all young people need in a future filled with smart machines and endless information.

Shift from Memorization to Meaning Instead of drilling facts, encourage your child to question sources. If you’re discussing a news article at dinner, ask: “How do we know this claim is accurate? What makes the source trustworthy?” Now they’re not just absorbing information; they’re actively working to understand it.

Foster Multimodal Exploration Make learning richer by using different approaches. Let them build a simple robot kit, draw a diagram of how it works, and then explain it in their own words. By connecting hands-on activity (tactile learning), visual learning, and verbal explanation, they develop deeper understanding.

Encourage Metacognition After solving a puzzle or coding a simple project, have them reflect: “What worked best? What would you try differently next time?” By understanding their own thought processes, they become better at adapting their approach to new challenges.

Highlight Interdisciplinary Connections and Global Outlook Show them that knowledge doesn’t exist in separate boxes. A math concept might connect beautifully with a musical pattern, or a historical event might be understood better through science. Help them see that good ideas and innovation come from everywhere in the world, not just one place or tradition.

Emphasize Emotional and Social Intelligence In a world where machines handle routine tasks, human qualities like empathy, communication, and teamwork become even more important. Encourage them to be comfortable with uncertainty, to see setbacks as chances to learn, and to develop resilience (the ability to bounce back from difficulties). These people skills will matter just as much as any technical knowledge.

Deep Learning and Entrepreneurial Thinking Like classical scholars who focused deeply on fewer subjects rather than skimming many, children benefit from spending more time thinking deeply about carefully chosen topics rather than rushing through lots of surface-level information. Consider teaching basic business and problem-solving skills early—like how to budget for a project or spot problems in their community that need solving—so they learn to create opportunities rather than just wait for them.

Finally, we’re raising children in an age where AI is becoming a constant helper and resource. While information is everywhere, the ability to understand it in context and make good judgments is rare and valuable. By using teaching techniques once reserved for gifted or 2e learners—multiple ways of learning, thinking about thinking, careful evaluation, global awareness, and creative combination of ideas—we prepare all children to be confident guides of their own learning. Instead of being overwhelmed by technology, they’ll learn to work with it, shape it, and use it to build meaningful futures.

This won’t happen overnight. But just as we adapted to big changes in the past, we can evolve again. We can model skepticism, curiosity, and flexible thinking at home. In doing so, we make sure that no matter how the world changes—no matter what new tools or systems appear—our children can stand on their own, resilient, resourceful, and ready to thrive in whatever tomorrow brings.

UPDATE [DEC 8,2024]: In the spirit of AI, I played with Claude 3.5 Sonnet yesterday and turned this post into a REACT presentation.

Technology bias—we all have it—but it often gets in the way.

Leave a reply

An old saying goes, “When you’re a plumber, you fix everything with a wrench.” It highlights a truth: we naturally gravitate toward the tools, people, and methods we know and trust most. This tendency stems from cognitive biases like anchoring—our reliance on initial information—and confirmation bias, which pushes us to favor ideas that align with our existing beliefs. While these biases help us make quick decisions, they can also blind us to better alternatives.

Another saying, “To know thyself is to be true,” resonates here. Even with my deep experience in PKI, I consciously revisit first principles whenever I consider applying it to a new problem. Is this really the best solution? PKI, like many technologies, carries hidden baggage that isn’t always visible, and over-reliance on familiarity can obscure better approaches.

The danger of sticking to the familiar becomes evident in the adoption of Infrastructure as Code (IaC). When tools like Terraform and CloudFormation emerged, many teams resisted, clinging to manual infrastructure management because it felt familiar and unnecessary. Yet manual approaches introduced inconsistency, inefficiency, and even security risks. Teams that embraced IaC unlocked scalable, repeatable workflows that transformed operations. IaC not only streamlined processes but also embedded elements of compliance and best practices directly into code. What outdated practices might we be holding onto today that prevent us from unlocking similar benefits?

I recently encountered a similar situation during a meeting with the leader of a large IT organization. They were eager to adopt a technology developed by someone they trusted personally. However, when I asked fundamental questions like, “How much time do you have to deliver this project?” and “What other systems need to interoperate for this to be considered a success?” it became clear that the technology wasn’t the right fit—at least not yet. By breaking the problem down to its fundamentals, we uncovered insights that their initial bias had obscured.

Practicing first-principles thinking can help sidestep these pitfalls. Start by identifying the core problem: what is the actual goal? What constraints are truly fixed, and which are merely assumptions? From there, challenge each assumption. Is there an alternative approach that better addresses the need? This process not only reduces the influence of bias but also fosters creativity and more effective solutions.

Biases aren’t inherently bad—they help us move quickly—but as the example of IaC demonstrates, unchecked bias can limit us. By anchoring decisions in first principles, we can do more than solve problems; we open the door to better solutions. Asking, “Is this truly the best approach?” ensures we don’t just repeat old patterns but discover new opportunities to improve and thrive.

Government CAs and the WebPKI: Trust is Often the Opposite of Security

Leave a reply

Following my recent post about another CA failing the “Turing test” with a likely MITM certificate issuance, let’s examine a troubling pattern: the role of government-run and government-affiliated CAs in the WebPKI ecosystem. This incident brings attention to Microsoft’s root program, what is clear is a fundamental contradiction persists: we’re trusting entities whose institutional incentives often directly conflict with the security goals of the WebPKI.

The Value Proposition

Let me be clear—CAs and root programs serve critical functions in the WebPKI. As I discussed in my article about Trust On First Use, attempting to build trust without them leads to even worse security outcomes. The issue isn’t whether we need CAs—we absolutely do. The question is whether our current trust model, which treats all CAs as equally trustworthy regardless of their incentives and constraints, actually serves our security goals.

The Core Contradiction

History has repeatedly shown that the temptation to abuse these capabilities is simply too great. Whether it’s decision-makers acting in their perceived national interest or CAs that fail to understand—or choose to ignore—the consequences of their actions, we keep seeing the same patterns play out.


Consider that a CA under government oversight faces fundamentally different pressures than one operating purely as a business. While both might fail, the failure modes and their implications for users differ dramatically. Yet our root programs largely pretend these differences don’t exist.

The DarkMatter Paradox

The removal of DarkMatter as a CA due to its affiliation with the UAE government, despite its clean record in this context, starkly contrasts with the continued trust granted to other government-affiliated CAs with documented failures. This inconsistency highlights a deeper flaw in root programs: Rules are often applied reactively, addressing incidents after they occur, rather than through proactive, continuous, and consistent enforcement.

A History of Predictable Failures

If you read yesterday’s post, you may recall my 2011 post on the number of government-run or affiliated CAs. The intervening years have given us a clear pattern of failures. Whether through compromise, willful action, or “accidents” (take that as you will), here are just the incidents I can recall off the top of my head—I’m sure there are more:

The Economics of (In)Security

The fundamental problem isn’t just technical—it’s economic. While some root programs genuinely prioritize security, inconsistencies across the ecosystem remain a critical challenge. The broader issue is not simply about convenience but about conflicting incentives—balancing compatibility, regulatory pressures, and market demands often at the expense of doing what is best for end users.


CAs face strong incentives to maintain their trusted status but relatively weak incentives to uphold the rigorous security practices users expect. The cost of their security failure is largely borne by users, while the benefits of looser practices accrue directly to the CA. Audits, much like those in financial scandals such as Wirecard or Enron, often serve as window dressing. With CAs selecting and paying their auditors, incentives rarely align with rigorous enforcement.


The long tail of rarely-discussed CAs is particularly concerning. Many root certificates in browser trust stores belong to CAs that issue only dozens to hundreds of certificates annually, not the thousands or millions that major CAs produce. Some haven’t issued a certificate in ages but retain the capability to do so—and with it, the ability to compromise security for months or longer. It wouldn’t be unreasonable to say these low-volume CAs pose risks far outweighing their utility.

Certificate Transparency: Necessary but Not Sufficient

While Certificate Transparency has been invaluable in helping identify incidents (including the latest ICP-Brasil case), it’s not a complete solution. Its limitations include:

  • Reactive nature: Violations are identified only after they occur.
  • Monitoring challenges: Effective oversight is resource-intensive and depends on a small community of volunteers.
  • Incomplete coverage: Not all certificates are logged, leaving gaps in visibility.
  • Poorly funded: We have too few logs and monitors to have confidence about the long-term survivability of the ecosystem.

The Limits of Technical Controls

Some browsers have implemented technical guardrails for some CA mistakes in their validation logic, such as basic certificate linting and rules, to reject certificates that don’t pass basic checks but nothing more granular. There have been discussions about imposing additional restrictions on CAs based on their relationship to government oversight or regulatory jurisdictions. However, these proposals face significant pushback, partly due to the political consequences for browser vendors and partly due to concerns about basing trust decisions on “future crime” scenarios. As a result, the WebPKI remains stuck with a one-size-fits-all approach to CA trust.

The Monitoring Gap

The challenges extend beyond malicious behavior to include operational oversight. For instance, in August 2024, ICP-Brasil formally announced they would cease issuing publicly trusted SSL/TLS certificates. Yet by November, they issued a rogue certificate for google.com. This outcome was predictable—public CT logs in 2020 revealed their consistent inability to handle basic operational and issuance requirements, including issuing certificates with invalid DNS names and malformed URLs. Despite these red flags, they remained trusted.


How many other CAs operate outside their stated parameters without detection? Patterns of technical incompetence frequently precede security incidents, but warnings are often ignored.

Required Reforms

To address these systemic issues, root programs must adopt the following measures:

  1. Consistent Standards: Apply appropriate scrutiny to CAs based on their operational and institutional context.
  2. Swift Response Times: Minimize delays between discovery and action.
  3. Proactive Enforcement: Treat red flags as early warnings, not just post-incident justifications.
  4. Technical Controls: Implement meaningful restrictions to limit the scope of certificate issuance.
  5. Automated Compliance: Require CAs to report security incidents, and operational, and ongoing compliance while continuingly to monitor them via automated checks for compliance.
  6. Value Assessment: Regularly evaluate whether each CA’s utility justifies its risks and remove those that do not.

Protecting Yourself

Until the ecosystem adopts consistent and enforceable security measures:

  • Windows users should monitor Microsoft’s root program decisions.
  • Enterprises should use the Microsoft distrust store and group policies.
  • Everyone should stay informed about CA incidents and their handling.

When Will We Learn?

The “Turing Test” reference in my previous post was somewhat tongue-in-cheek, but it points to serious questions: How many more failures will it take before we fundamentally reform the WebPKI? Even if we know what’s needed, can we realistically create a system that treats government-affiliated CAs differently – or even reliably identify such affiliations – given the complex web of international relations, corporate structures and potential diplomatic fallout?

With regulatory frameworks like eIDAS 2.0 potentially constraining security measures browsers can take, vigilance from the security community is more critical than ever. Stay vigilant, and keep watching those CT logs. Someone has to.

Another CA Fails the Turing Test?

Leave a reply

In a concerning development, yet another Certificate Authority (CA) has issued what is likely a man-in-the-middle (MITM) certificate—something strictly prohibited by all root programs. This particular case is unique because the CA is trusted only by Microsoft, making the situation both frustratingly familiar and uniquely problematic. Details are emerging in this Bugzilla thread.

A Familiar Pattern

Back in 2011, I wrote about Microsoft’s trust in government-run CAs and the inherent risks (read here). More than a decade later, it’s clear little has changed. Browser distrust events happen with disappointing regularity—roughly every 1.25 years, according to my analysis (source). While MITM certificate issuance is far rarer, it’s far more serious, and a disturbing trend is evident: Many of the CAs responsible are government-run or affiliated.

Why This Matters to You

For Windows users, this is particularly relevant. Windows browsers like Edge (and others) rely on the Microsoft Root Program, which has unfortunately historically been overly permissive and slow to respond to incidents. You can learn more about the program and its requirements here. In the recent past, I can’t recall a CA responsible for willfully issuing an MITM certificate surviving, but the the timeline for Microsoft’s response is unclear. That said, when Microsoft does act, their AutoRoot Update feature—which I was the product manager for in the early 2000s—allows them to respond swiftly.

In the meantime, you can protect yourself by identifying and distrusting the offending certificate. Enterprises, in particular, can take a proactive stance by using the Microsoft distrust store. Through group policy, IT administrators can preemptively distrust the problematic CA across their organization, mitigating the risk before Microsoft formally acts.

The Lack of Technical Controls

It’s worth noting there are no technical controls that inherently prevent CAs from issuing MiTM certificates (though some browsers do have technical controls for some classes of misissuance). Instead, the WebPKI ecosystem relies on Certificate Transparency (CT) logs and a dedicated community of people closely monitoring CA issuance for violations of requirements. In a way, this incident serves as a smoke test for the system—but when it comes to these MITM certificates, it’s an awfully expensive test, with significant risks both for users of the web and reputational risks for the root programs, as well as questions about the trustworthiness of the WebPKI in general.

Predictable Chaos

If you’re following this story, keep an eye on the Bugzilla thread. Based on past experience, I’d wager the CA in question will bungle its incident response. MITM certificate issuance often reflects systemic issues, and such organizations typically don’t have the maturity to handle these crises well.

If this topic interests you, here’s some further reading:

For a deeper dive, here’s a class I run on the topic of WebPKI incident response and how they’re (mis)handled.

Lessons Unlearned

While it’s comforting to know mechanisms like Certificate Transparency exist to catch these incidents, the recurring nature of these failures raises the question: Are we doing enough to hold CAs accountable?

Trust in the web depends on the reliability of its foundational systems. It’s time we demand higher standards from the organizations entrusted with securing our online world. Until then, stay informed, protect yourself, and let’s hope the next CA at least manages to pass the “Turing Test.”

Proactive Security: Engineering Resilience from the Ground Up

3 Replies

Picture discovering your house has been robbed. Like many homeowners in this situation, your first instinct might be to invest in the latest security system with cameras and motion sensors. But what if the thief simply walked through an unlocked door, exploiting the most basic failure of security? No amount of surveillance would have prevented such a fundamental oversight.

This scenario mirrors how many organizations approach security today. Companies invest heavily in sophisticated detection and response tools and a patchwork of workarounds to basic design flaws while neglecting basic security practices, creating a false sense of security all built on a shaky foundation. According to Gartner, global cybersecurity spending reached $188.3 billion in 2023, yet breaches continue to rise because we’re treating symptoms while ignoring their root causes.

The Real Cost of Reactive Security

Detection and monitoring tools can provide valuable insights but cannot compensate for fundamental security weaknesses. Many organizations invest heavily in sophisticated detection capabilities while leaving basic architectural vulnerabilities unaddressed—much like a house with state-of-the-art cameras but unlocked doors.

The U.S. Government Accountability Office recently highlighted this problem in stark terms: ten critical federal IT systems, ranging from 8 to 51 years old, cost taxpayers $337 million annually to maintain. Many of them rely on obsolete technologies like COBOL, where maintenance costs continue to rise due to scarce expertise. The thing is that we’ve learned a lot about building secure systems in the last 51 years — as a result, these systems have no chance when faced with a moderately skilled attacker. While government systems make headlines, similar issues affect private enterprises, where legacy systems persist due to the perceived cost and risk of modernization.

The persistence of basic security flaws isn’t just a technical failure; it often represents a systemic underinvestment in foundational security architecture. Consider weaknesses such as:

  • Outdated Architectures
    Decades-old systems that cannot meet modern security demands.
  • Minimal Security Hygiene
    Poor patching practices, weak service-to-service authentication, and a lack of hardened or unikernel images.
  • Weak Design Principles
    Core concepts like zero trust and least privilege can not be bolted on later leaving systems exposed.
  • Lack of Lifecycle Planning
    Without clear modernization plans, organizations face costly and disruptive migrations when problems inevitably arise.

These issues are not just hypothetical. For example, the Salt Typhoon espionage campaign exploited foundational weaknesses to compromise major U.S. telecom firms, including Verizon, AT&T, and T-Mobile. Such systemic flaws make even the most advanced detection systems insufficient.

Building Security from the Ground Up

For years, the cybersecurity industry has embraced the mantra, “security is everyone’s problem.” While this has broadened awareness, it often leads to unintended consequences. When responsibility is shared by everyone, it can end up being truly owned by no one. This diffusion of accountability results in underinvestment in specialized security expertise, leaving critical vulnerabilities unaddressed. The Microsoft Storm-0558 incident serves as a prime example of the risks posed by this approach.

True security requires a fundamental shift from reactive to proactive approaches. Organizations must design systems assuming they will eventually be compromised. This means embedding zero trust principles, implementing proper system segmentation, and treating least privilege as foundational.

In practice, proactive measures include short-lived credentials, mutual TLS authentication, and granular access controls from the outset. For example, while a reactive approach might detect suspicious service-to-service communication, a proactive approach prevents such movement entirely through robust authentication.

Security in the Development Process

The development process itself should prioritize security through specific, measurable practices. Best-in-class organizations typically implement:

  • Infrastructure as code with built-in security policies.
  • Hardened containers or unikernel images to reduce attack surfaces.
  • Automated patch management integrated into deployment pipelines.
  • Continuous compliance monitoring and reporting for real-time security assurance.

These aren’t just best practices—they’re competitive advantages. Organizations that adopt them often see reduced incident costs and faster recovery times, transforming security from a cost center into an enabler of resilience and growth.

Regulatory Progress and Its Limitations

The U.S. Cybersecurity and Infrastructure Security Agency (CISA) introduced its Secure by Design pledge to encourage security-first practices. While this initiative represents progress, it lacks critical components:

  • No Accountability
    There are no enforcement mechanisms to ensure organizations uphold their commitments.
  • No Tracking
    Without benchmarks or reporting requirements, evaluating progress is impossible.
  • No Timeline
    The absence of deadlines allows organizations to deprioritize these efforts indefinitely.

Without these elements, the pledge risks becoming aspirational rather than transformative. As seen with other voluntary efforts, real change often depends on market pressure. For instance, if cloud providers demanded stronger security controls from vendors, or if enterprises baked security requirements into procurement, the market would likely respond more effectively than through regulation alone.

A Balanced Security Strategy

Organizations must balance strong foundations with effective monitoring through clear, measurable steps:

  1. Thoroughly Evaluate Legacy Systems
    Identify critical systems, document dependencies, and create modernization plans with timelines.
  2. Embed Security Into Development
    Use security champions programs, establish clear ownership for each system, and incentivize proactive measures.
  3. Leverage Proactive Security Measures
    Implement short-lived credentials, granular privileges, and zero trust principles during design and operation.
  4. Strategically Deploy Reactive Tools
    Use detection and response systems to validate security assumptions and provide early warning of issues, not to compensate for poor design.

Proactive and reactive measures are complementary, not competing priorities. Installing advanced monitoring on a fundamentally weak system offers organizations only a false sense of security. By contrast, strong proactive foundations reduce the need for reactive interventions, cutting costs and lowering risks.

Conclusion: The Cost of Inaction

The choice between proactive and reactive security isn’t theoretical—it’s an urgent and practical decision. Systems designed with security in mind experience fewer breaches and cost less to maintain. The CISA Secure by Design pledge is a step in the right direction, but without accountability and market-driven enforcement, its impact will remain limited.

Organizations face a clear path forward: invest in proactive security measures to reduce systemic risks while leveraging reactive tools as a safety net. As cyber threats continue evolving, the question is not whether proactive security is necessary, but how soon organizations will act to implement it. Don’t wait until it’s too late—fix the house before adding stronger deadbolts.

From Years to Seconds: Rethinking Public Key Infrastructure

Leave a reply

Public Key Infrastructure was designed for a world where identities persisted for years—employees joining a company, servers running in data centers, devices connecting to networks. In this world, the deliberate pace of certificate issuance and revocation aligned perfectly with the natural lifecycle of these long-lived identities. But today’s cloud-native workloads—containers, serverless functions, and microservices—live and die in seconds, challenging these fundamental assumptions.

Though these ephemeral workloads still rely on public key cryptography for authentication, their deployment and management patterns break the traditional model. A container that exists for mere seconds to process a single request can’t wait minutes for certificate issuance. A serverless function that scales from zero to thousands of instances in moments can’t depend on manual certificate management. The fundamental mismatch isn’t about the cryptography—it’s about the infrastructure and processes built around it.

This isn’t a problem of public key infrastructure being inadequate but rather of applying it in a way that doesn’t align with modern workload realities. These new patterns challenge us to rethink how authentication and identity management systems should work—not just to ensure security, but to support the flexibility, performance, and speed that cloud-native infrastructure demands.

Why Workloads Are Different

Unlike human or machine identities, workloads are ephemeral by design. While a human identity might persist for years with occasional role changes, and a machine identity might remain tied to a server or device for months, workloads are created and destroyed on-demand. In many cases, they live just long enough to process a task before disappearing.

Unlike human and machine identities where identifiers are pre-assigned, workload identifiers must be dynamically assigned at runtime based on what is running and where. This transient nature makes revocation—a cornerstone of traditional PKI—irrelevant. There’s no need to revoke a workload’s credentials because they’ve already expired. In fact, much like Kerberos tickets, workload credentials are short-lived by design, issued for just long enough to meet deployment SLAs.

The Identity Lifecycle Dynamics graphic below illustrates these differences clearly:

  • Human identities are persistent, often spanning years, with sequential changes governed by compliance and auditing processes.
  • Machine identities are semi-persistent, lasting weeks or months, with planned updates and automated renewals sometimes tied to devices or hardware lifetimes.
  • Workload identities, by contrast, are ephemeral. They join and leave almost instantly, with lifespans measured in minutes and operations occurring at massive scale.

Compounding this difference is the scale and speed at which workloads operate. It’s not unusual for thousands of workloads to be created simultaneously, each requiring immediate authentication. Traditional PKI processes, designed for slower-moving environments, simply can’t keep up. And workloads don’t just operate in isolation—they’re often distributed across multiple regions to minimize latency and avoid unnecessary points of failure. This means the supporting credentialing infrastructure must also be distributed, capable of issuing and verifying credentials locally without introducing bottlenecks or dependency risks.

Governance adds another layer of complexity. While human and machine identities are often subject to compliance-driven processes focused on auditability and security, workloads are governed by operational priorities:

  • Zero downtime: Workloads must scale rapidly and without disruption.
  • Regional performance: Authentication systems must match the workloads’ regional deployments to avoid latency.
  • Developer flexibility: Identity systems must integrate with whatever technology stacks developers are already using.

The lifecycle of a workload identity reflects the immediacy of software deployment cycles, rather than the structured schedules of hardware or personnel management.

Rethinking Identity Infrastructure for Workloads

The traditional PKI model isn’t going away—it remains essential for the stable, predictable environments it was designed to support. But workloads require a shift in approach. They demand systems capable of:

  • Dynamic credential issuance: Credentials must be created on-demand to support rapid scaling, with automated identifier assignment based on runtime context and workload characteristics.
  • Ephemeral lifecycles: Workload credentials should expire automatically, eliminating the need for revocation, with lifecycle durations matched to actual workload runtime requirements.
  • Multi-factor workload authentication:  Something the workload has (hardware roots of trust, cryptographic keys), something the workload knows (runtime configuration), something the workload is (attestation data, container hashes, process metadata).
  • Distributed infrastructure: Regional authentication systems ensure low latency and high availability, with local credential issuance capabilities.
  • Massive scalability: Systems must support thousands of identity events per minute, operating across clouds or hybrid environments, with automated identifier management at scale.
  • Runtime identifier assignment based on: What is running (container hashes, process information), Where it’s running (environment context, runtime attestation), how it’s running (execution environment verification).

As highlighted in the lifecycle comparison, workload identities aren’t simply a smaller, faster version of machine identities. Their governance models reflect their role in delivering business-critical objectives like seamless scaling and developer empowerment.

Perhaps the most significant difference is the role of developers. Workload identity systems can’t impose rigid, one-size-fits-all requirements. Developers need the freedom to:

  • Work with existing technology stacks.
  • Seamlessly integrate identity management into their workflows.
  • Build and deploy at the speed demanded by modern infrastructure.

In this way, workload identity management becomes not just a security task but a foundational enabler of innovation and efficiency.

Taking the First Step with SPIFFE

SPIFFE (Secure Production Identity Framework For Everyone) is an open standard designed to enable workloads to automatically acquire identities, certificates, and OIDC tokens for secure zero-trust communication between services. Rather than retrofitting existing systems, look for upcoming greenfield deployments where you can engage early in the design phase. This allows you to build SPIFFE’s workload identity patterns in from the start—solving different problems than traditional PKI, not competing with it. Use this greenfield project to demonstrate how PKI as a technology via SPIFFE can help solve additional problems for production environments.

Final Thoughts

Workloads have redefined how we think about identity. They operate at a speed and scale that traditional PKI never anticipated, governed by different priorities and lifecycles that reflect the realities of modern software. While PKI will continue to serve as a critical component of authentication, it must evolve to meet the unique demands of ephemeral, distributed workloads.

This isn’t about abandoning the tools we rely on but about adapting them for a world where zero downtime, developer flexibility, and seamless scalability are non-negotiable. The future of identity isn’t static or centralized—it’s dynamic, distributed, and built to support workloads that define modern infrastructure.

For organizations looking to implement these patterns quickly and efficiently, SPIRL (a company I advise) provides tools to make workload identity management straightforward and accessible.

   

Bundling and Unbundling in the NHI Market: Opportunities in Identity, Governance, and Cryptography

Leave a reply

Jim Barksdale famously said “All money is made through bundling and unbundling,” and this dynamic is evident in the Non-Human Identity (NHI) market. Cryptography management, privileged access management, and certificate lifecycle solutions are being redefined under a higher-level taxonomy. These functions, once viewed as isolated, are increasingly integrated into broader frameworks addressing identity, governance, and security holistically, reflecting the market’s shift toward unified and specialized solutions.

Cloud providers dominate in offering integrated solutions across categories, but these are often limited and focus on cost-recovery pricing to encourage adoption of their real money-makers like compute, storage, network, databases, and these days AI. They frequently provide just enough to facilitate a single project’s adoption, leaving opportunities for other vendors. For instance, Microsoft’s push to migrate enterprises from on-premises Active Directory to its cloud offering presents an opportunity to unbundle within the NHI IAM space. By focusing narrowly on migrating existing infrastructures rather than reimagining solutions from first principles to meet modern usage patterns, Microsoft has created gaps that smaller, more agile providers can exploit. Similarly, regulatory pressures and the rise of AI-driven, agentic workloads are driving demand for advanced workload authentication, creating further opportunities for specialized providers to deliver tailored solutions. Meanwhile, established players like CyberArk and Keyfactor have pursued acquisitions, such as Keyfactor’s merger with PrimeKey, to bundle new capabilities and remain competitive. However, the integration complexity of these acquisitions often leaves room for focused providers to address modern, cloud-native demands more effectively.

At the same time, traditional cryptography management companies have been so focused on their existing Key Management System (KMS) and Hardware Security Module (HSM) offerings that they have largely ignored broader unmet needs in the market, prioritizing feature expansion and acquisitions aimed at chasing smaller competitors. This narrow focus has left significant gaps in visibility, particularly around cryptographic assets and risks, creating fertile ground for new solutions focused on cryptography discovery, automated inventory management, and preparation for post-quantum cryptography.

Capital allocation, on the other hand, highlights category focus and growth potential. Seed and Series A investments underscore the dynamic opportunities created by unbundling, as well as the constraints faced by larger vendors burdened with legacy products that make it harder to truly innovate due to existing commercial obligations in the same space. In contrast, private equity activity targets larger bundling opportunities, enabling less agile and more mature market leaders to remain relevant by scaling established solutions or consolidating fragmented players. These stages illustrate the market’s balance between early-stage innovation and late-stage consolidation, driven by the growing demand for unified, cloud-native identity and governance solutions.

These patterns of bundling and unbundling are organic and continual, offering just one lens on the evolving dynamics of this market. While the NHI market appears new, it is, in fact, a natural evolution of existing identity governance patterns, driven by the growing demand for unified, cloud-native identity and governance solutions. This evolution underscores the balance between early-stage innovation and late-stage consolidation, as new entrants and established players alike navigate the opportunities created by shifting market dynamics.

Rethinking Authentication: “Something You Have,” “Something You Know,” and “Something You Are” for Workloads and Machines

1 Reply

Passwords have existed for millennia, and their weaknesses have persisted just as long. Their simplicity led to widespread adoption, but as their use expanded, so did the frequency of their abuse. To address this, we implemented stricter password policies—longer lengths, special characters, regular changes—much like hiding vulnerable software behind firewalls. When these efforts fell short, we evolved to multi-factor authentication (MFA), introducing the principles of “Something You Have,” “Something You Know,” and “Something You Are.”

MFA brought its own challenges—deployment complexity and user friction. Password managers helped bridge some gaps by generating and storing random passwords for us. While each of these steps enhanced security, none addressed the core problem: passwords and shared secrets are fundamentally flawed authenticators. This realization spurred efforts like WebAuthn, FIDO, and Passkeys, which replaced passwords with cryptographic keys and secure protocols, eliminating shared secrets entirely.

However, while user authentication evolved, workload and machine authentication lagged behind. Instead of passwords, workloads relied on API keys—essentially shared passwords—managed through “password managers” rebranded as secret vaults. These shared secrets are just as fragile and inadequate for today’s complex, scaled environments as passwords were for users.

The path forward is clear: workloads and machines need their own authentication revolution. We must replace shared secrets with cryptographic keys and implement MFA for workloads. But what does machine-focused MFA look like? Let’s explore how the three fundamental authentication factors apply to workloads and machines.

Applying Authentication Factors to Workloads and Machines

1. Something the Workload Has

This encompasses physical or cryptographic elements unique to the workload:

  • Hardware Roots of Trust: Security processors like TPM, Microsoft Pluton, Google Titan, and Apple’s Secure Enclave provide tamper-resistant foundations for device identity and posture assessment.
  • Cryptographic Keys: Private keys secured within hardware security processors serve as a robust “something you have,” enabling strong authentication.
  • Credentials: Like OIDC tokens and X.509 certificates, uniquely identify machines and workloads within trusted environments.

These mechanisms form the backbone of secure workload authentication, much like physical security tokens do for human users.

2. Something the Workload Knows

This parallels knowledge-based authentication but focuses on workload-specific secrets:

  • Shared Secrets: Shared API keys, symmetric keys, and asymmetric credentials that are used for authentication.
  • Configuration Data: Runtime-specific information like environment configuration.

Although often necessary for a service’s functionality, these weak attributes are highly susceptible to exposure, reuse, and theft. Implementing credentialing systems like SPIFFE can significantly mitigate these risks by replacing shared secrets with cryptographically secure, short-lived credentials uniquely tailored to each workload.

3. Something the Workload Is

This represents inherent characteristics of the workload, similar to human biometrics:

  • Trusted Execution Environments (TEEs): Secure enclaves like Intel SGX or AWS Nitro verify and attest to the integrity of the workload’s execution environment.
  • Immutable Code or Container Hashes: Binary or container image hashes verify workload integrity.
  • Runtime Attestation: Environmental and configuration validation ensures compliance with security policy.
  • POSIX Process Names and Metadata: Process information and runtime metadata provide operational context.

By combining these attributes, workloads can demonstrate their role and environment to enable more contextual identification and authorization.

The Future of Workload Identity

Authentication factors vary in strength—cryptographic keys and runtime attestations can provide strong confidence in what you are talking to while process names and secrets offer weaker assurance. Combining these elements creates a more comprehensive picture of workload authenticity. Standards like SPIFFE leverage this combination, creating strong workload identities by incorporating hardware roots of trust, runtime attestations, and other security properties. Over time, these attestations can be enriched with supply chain provenance, vulnerability assessments, and other compliance data.

As we look further ahead to agentic workloads and AI systems, we will need to develop protocols and policies that enable us to consider both workload identity and the entities they represent. For example, an AI model handling financial transactions needs both verified workload identity and specific policies for each user it serves so that the agent does not become a way to escalate privileges and access data that would otherwise have been unreachable.

This evolving, layered approach ensures that workload authentication scales with increasingly complex machine ecosystems while maintaining security and accountability. By unifying identity, actions, and policies, we prepare for a future of autonomous yet accountable workloads.

The Myth of Non-Technical Product Management

Leave a reply

A common theme in conversations about product managers is the notion that they don’t need to be technical; they just need to bridge the gap between technical and non-technical teams. In my experience, particularly with enterprise and security products, this is a complete fallacy. Part of why this argument persists is the misconception that all product management is the same.

If you’re working on a 10-year-old product based on 20-year-old deployment patterns—and this might be hard to hear—chances are you’re not innovating. Instead, you’re managing customer requests and operating within the constraints of the bureaucracy you’re part of. Your roadmap likely consists of a mix of customer demands and features cloned from smaller competitors.

Another reason this perspective persists is that many organizations divide product managers into two categories: inbound and outbound. Outbound product managers are this decade’s version of product MBAs. They often have a limited understanding of their customers and their needs, instead focusing on systematizing a go-to-market strategy based on abstractions.

In the problem domain of enterprise and security—especially in small to medium-sized companies, where innovation tends to happen—there is no substitute for being an expert in what you’re building and selling. One of the most important things to understand is your customer: their pains, their constraints, and the schedules they operate within. The thing is, your customer isn’t just one person in an enterprise sale. As I’ve written before, at a minimum, you’re dealing with an economic buyer and a champion in any sale. If you’re lucky, you have many champions. And if you think strategically, you can even identify your champions’ champions within the sale.

This requires you to understand everyone’s job and perspective. If you don’t understand the technology or problem domain natively, you will always struggle—and likely fail—especially in smaller, early-stage companies.

Don’t get me wrong: once a company finds product-market fit and has a reproducible recipe for selling into organizations—or as the market evolves and expectations for a product in a given segment become standardized—it becomes less necessary. But even then, bringing that expertise to the table remains a powerful force multiplier that enables organizations lucky enough to have these resources to vastly outperform much larger and better-funded competitors.

Since I spend most of my time these days with smaller companies or very large companies looking to become more competitive again, all I can say is this: without the right product leaders, the best you can hope for is growing at the pace of your overall market and maintaining the status quo.