AI Accelerates Coding, Short-Lived Certificates Complicate Trust - Episode Hero Image

AI Accelerates Coding, Short-Lived Certificates Complicate Trust

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TL;DR

  • The shift to short-lived (e.g., three-day) code signing certificates, driven by certificate authorities, significantly increases costs for developers and enterprises, forcing a move to cloud-based signing services and per-signature fees.
  • Microsoft's Azure Trusted Signing service offers a more affordable alternative for code signing, though it involves navigating complex Azure infrastructure and has a steep learning curve for setup.
  • The increasing cost and complexity of code signing, coupled with shortened certificate lifetimes, are creating an opportunity for new, potentially lower-cost certificate authorities to emerge.
  • Code signing certificates primarily assert the signer's identity and code integrity at the time of signing, unlike TLS certificates which require ongoing validity for real-time authentication.
  • Time stamping authorities (TSAs) provide a crucial layer of trust for code signing by anchoring signatures to a specific point in time, ensuring long-term validity even after the signing certificate expires.
  • The rise of AI coding assistants like Claude Code is dramatically accelerating software development, enabling even non-programmers to create custom applications and empowering expert coders to work more efficiently.
  • California's new data broker opt-out law (DROP) provides a mechanism for residents to request data deletion, but requires extensive personal information disclosure and relies on data brokers' compliance.

Deep Dive

The proliferation of AI coding assistants is fundamentally altering the software development landscape, democratizing creation while simultaneously introducing new complexities and security challenges. This shift is evidenced by the emergence of short-lived code-signing certificates and the increasing difficulty of managing digital trust, forcing developers and organizations to adapt to more dynamic and potentially costly security models.

The primary implication of AI-driven coding is its ability to accelerate development and lower the barrier to entry for software creation. Tools like Claude Code and Andrew Ng's "Build with Andrew" course empower individuals without traditional coding backgrounds to describe and build applications, bridging the gap between technical and non-technical roles. This democratization, however, is accompanied by significant upstream and downstream effects. For developers, AI assistants act as powerful accelerators, handling boilerplate code, debugging, and even architectural planning, allowing them to focus on higher-level problem-solving and innovation. This efficiency gain, while beneficial, also means that the skills required for software development are evolving, shifting focus from rote coding to prompt engineering, system design, and managing AI-generated outputs.

Concurrently, the infrastructure supporting code integrity is undergoing a significant transformation. The traditional model of long-lived code-signing certificates is being challenged by the increasing prevalence of short-lived certificates, exemplified by Microsoft's three-day certificates. This change is driven by a desire to "aggressively thwart invalid signing attacks," particularly in cloud-based signing services where keys are managed by a third party. The consequence for developers is increased administrative overhead and potentially higher costs, as certificates need more frequent renewal. Furthermore, the reliance on cloud-hosted signing keys and the introduction of services like Azure Trusted Signing create a complex ecosystem where organizations must navigate intricate setup processes and manage dependencies. This shift from self-managed keys to service-based solutions represents a trade-off: enhanced security against key compromise at the cost of greater complexity and vendor dependence.

The implications extend to the very notion of digital trust. While TLS certificates for web servers require real-time validation, code-signing certificates historically asserted a static trust based on the signer's identity and the integrity of the code at the time of signing. The introduction of short-lived certificates and the reliance on Time Stamp Authorities (TSAs) add a dynamic layer, ensuring that the validity of a signature is anchored to a specific point in time, regardless of the subsequent expiration of the signing certificate. This is crucial for maintaining the long-term trustworthiness of software, preventing scenarios like the recent Logitech app failures due to expired certificates. For organizations, this necessitates a robust strategy for managing certificate lifecycles and integrating TSA services to ensure perpetual validity of signed code. The increasing costs and complexities associated with these changes could also create barriers for smaller developers and businesses, potentially leading to a consolidation of power within certificate authorities and cloud providers.

In essence, the rise of AI in coding and the evolving landscape of code-signing certificates signal a paradigm shift. While AI promises to make software creation more accessible and efficient, it also necessitates a re-evaluation of how we establish and maintain trust in digital assets. Organizations must adapt to shorter certificate lifecycles, embrace cloud-based signing solutions, and understand the role of time-stamping to ensure the ongoing integrity and trustworthiness of their software in an increasingly dynamic digital world.

Action Items

  • Audit code signing certificates: Verify validity at the time of signing for all released software, ensuring timestamping services are utilized.
  • Implement automated certificate renewal: Establish a process for timely renewal of code signing certificates to prevent service disruptions.
  • Evaluate Azure Trusted Signing: Compare its pricing and functionality against traditional certificate providers for potential cost savings and efficiency.
  • Investigate certificate management policies: Review internal policies regarding certificate storage and usage to identify potential security or operational risks.
  • Develop a fallback strategy for expired certificates: Plan for scenarios where software relies on expired certificates, outlining mitigation steps.

Related Episodes

Key Quotes

"The new rules don't allow for locally stored exportable certificates instead certificates have to be served from one of a few certified online authorities or the certs stored in a fips 140 2 level 2 plus compliant hardware security module the keys cannot be exportable so they effectively cannot be copied and stored or used elsewhere so you got the option of a server provided keys or hardware keys"

This quote from Rick Stroll highlights a significant shift in code signing certificate requirements. Stroll explains that certificates are no longer allowed to be stored locally and exportable. Instead, they must be managed through certified online authorities or secured within specific hardware modules, indicating a move towards more centralized and restricted key management.

"The certificates issued by microsoft are very short lived with expirations that last only three days to aggressively thwart invalid signing attacks in cases where the certificate is compromised thus the title of today's podcast three day certificates we're going to look at the mechanisms behind that"

Rick Stroll introduces the concept of "three-day certificates" in this quote, explaining their purpose. Stroll notes that Microsoft's Azure Trusted Signing service issues certificates with very short lifespans to proactively combat attacks that might exploit compromised certificates. This short duration is intended to limit the window of vulnerability.

"The process to set up trusted signing was way harder than it should have been in fact the entire process took me the better part of an entire workday the server process is complicated primarily because the nomenclature is so crazy confusing and the dependency management on azure is such a pain in the ass"

Rick Stroll expresses frustration with the complexity of setting up Microsoft's Azure Trusted Signing service. Stroll details that the setup process was time-consuming and difficult, attributing this to confusing terminology and intricate dependency management within the Azure platform. This suggests that while the service may offer benefits, its implementation is far from straightforward.

"The certificates issued by microsoft are very short lived with expirations that last only three days to aggressively thwart invalid signing attacks in cases where the certificate is compromised thus the title of today's podcast three day certificates we're going to look at the mechanisms behind that"

Steve Gibson uses this quote from Rick Stroll to introduce the central topic of the podcast. Gibson highlights Stroll's observation about Microsoft's use of three-day code signing certificates, emphasizing their purpose in thwarting attacks by limiting the validity period of compromised certificates. This sets the stage for a deeper exploration of how such short-lived certificates function.

"The signing certificate may have expired but what's the enforcement mechanism for its expiration we might suggest that the pc used to perform the signing would examine the certificate and see that it had expired okay the bad guys know that their stolen certificate has expired so they simply turn back the clock on the signing pc that they're using to a point where the certificate is valid now the pc believes that the certificate is valid and in good standing it has no way of knowing what day it is"

Steve Gibson explains a potential vulnerability related to expired code signing certificates. Gibson points out that without a proper enforcement mechanism, malicious actors could manipulate the system clock on a signing PC to make an expired certificate appear valid. This highlights the importance of additional verification beyond just the certificate's expiration date.

"Introducing the tsa a different kind of tsa this is the time stamp authority a time stamp authority is a trusted third party it's typically a certificate authority and is often but not necessarily the same ca who provided the signing certificate in the first place it is a service that cas offer during the code signing process"

Steve Gibson introduces the Time Stamp Authority (TSA) as a crucial component in code signing. Gibson explains that a TSA is a trusted third party, often a Certificate Authority, that provides an unforgeable timestamp for signed code. This timestamp verifies the validity of the signature at the moment it was created, regardless of the signing certificate's later expiration.

Resources

## External Resources

### Books
- **"The Magnesium Miracle"** by Carolyn Dean - Mentioned as a book recommendation that led to increased magnesium intake.
- **"Magnesium: The Missing Link to Total Health"** by Carolyn Dean - Mentioned as an updated version of "The Magnesium Miracle" with recent research.

### Articles & Papers
- **"Fighting Through Setting Up Microsoft Trusted Signing"** by Rick Stroll (Blog Post) - Discussed as an inspiration for the podcast's topic on three-day certificates and a detailed guide to setting up Microsoft Azure Trusted Signing.

### People
- **Rick Stroll** - Author of a blog post on Microsoft Trusted Signing, providing context on code signing certificate changes and pricing.
- **Andrew Ng** - Founder of DeepLearning.AI, cited for a free course on building apps with AI for non-coders.
- **Al Liebel** - Listener who developed an open-source project using AI coding tools, sharing his experience with Claude Code.
- **Carolyn Dean** - Author of "The Magnesium Miracle" and "Magnesium: The Missing Link to Total Health."
- **Steve Pennefold** - Listener who provided an update on the latest editions of Carolyn Dean's book on magnesium.
- **T.J. Asher** - Listener who shared insights on the cost and challenges of code signing certificates for enterprises.
- **Jay Thompson** - Listener who inquired about starting a certificate authority service.
- **Scott** - Listener who expressed appreciation for comments on vitamins and security advice.
- **Joey Albert** - Listener who enjoyed "The Lazarus Project" series.
- **Mr. Ron** - Listener who also enjoyed "The Lazarus Project" series.
- **Philip** - Listener who raised concerns about the impact of shorter code signing certificate lifetimes.

### Organizations & Institutions
- **Microsoft** - Mentioned for its Azure Trusted Signing service for code signing.
- **DigiCert** - Mentioned as the certificate authority that issued a code signing certificate for GRC.
- **Identrust** - Mentioned as a certificate authority that cross-signed Let's Encrypt's root certificate.
- **Let's Encrypt** - Mentioned as an example of a certificate authority that bootstrapped trust through cross-signing.
- **Apple** - Mentioned in relation to its built-in Mail app and the App Store search results.
- **T-Mobile** - Mentioned in the context of a phishing text message.
- **Amazon** - Mentioned in the context of a phishing text message.
- **US National Weather Service** - Mentioned for withdrawing a wind forecast due to AI-generated fictitious town names.
- **DeepLearning.AI** - Publisher of "The Batch" newsletter and host of a free course on AI coding.
- **GRC (Gibson Research Corporation)** - Host of the podcast and provider of the Never10 executable.
- **Hoxhunt** - Sponsor of the podcast, offering a security training platform.
- **Material** - Sponsor of the podcast, providing a cloud workspace security platform.
- **Cloudflare** - Mentioned as a service provider for the consumer drop privacy website.
- **California Privacy Protection Agency (Cal Privacy)** - Agency responsible for the DROP platform.
- **Secure.login.gov** - Mentioned as a third-party vendor assisting with California residency verification.
- **Fast SSL** - Brand offering non-EV code signing certificates.
- **Cheap SSL Security.com** - Website where Fast SSL certificates are available.
- **Logitech** - Mentioned for its Options+ and G Hub apps on macOS breaking due to an expired certificate.
- **Bleeping Computer** - Publication that reported on Logitech apps breaking after certificate expiration.
- **Isrg Root X1** - Let's Encrypt's root certificate.

### Websites & Online Resources
- **consumerdrop.privacy.ca.gov** - Website for the California data broker opt-out platform (DROP).
- **grc.com** - Website associated with Steve Gibson.
- **grcscodesign** - GRC shortcut to Rick Stroll's blog post.
- **grcscandrew** - GRC shortcut to Andrew Ng's AI coding course.
- **hoxhunt.com/securitynow** - Website for Hoxhunt.
- **material-security.com** - Website for Material.
- **twit.tv/club** - Website for TWiT+ club memberships.
- **github.com/leoreport/rss-reader** - Public GitHub repository for Leo's RSS reader.

### Other Resources
- **Claude Code** - AI coding tool mentioned as a life-changing accelerant for development.
- **Azure Trusted Signing** - Microsoft's cloud code signing service.
- **DROP (Delete Request and Opt-Out Platform)** - California's platform for data broker opt-out.
- **Global Privacy Control (GPC)** - Browser setting for privacy preferences.
- **Time Stamp Authority (TSA)** - Trusted third party service for timestamping code signatures.
- **Never10** - GRC's Windows executable program.
- **The Lazarus Project** - TV series recommended by listeners.
- **For All Mankind** - TV series mentioned as a speculative fiction about the space race.
- **HyperCard** - Apple's software for creating interactive applications.
- **Visicalc** - Spreadsheet software that allowed users to do what they wanted with numbers.
- **Awesome Claude** - GitHub page with resources for using Claude's skills.
- **Ralph Wiggum** - A tool mentioned for iterating until a goal is met.
- **Opal** - Google's tool designed to use Gemini for creating AI apps for non-technical users.
- **Code Signing Certificates** - Digital certificates used to verify the identity of software publishers and the integrity of their code.
- **TLS Certificates** - Certificates used for web server authentication.
- **Hardware Security Module (HSM)** - Secure hardware device for storing cryptographic keys.
- **FIPS 140-2 Level 2+** - Security standard for hardware security modules.
- **EV Certificates (Extended Validation)** - A type of code signing certificate requiring more rigorous vetting.
- **ACME (Automated Certificate Management Environment)** - Technology for automating certificate management.
- **IMAP (Internet Message Access Protocol)** - Protocol for retrieving email.
- **TCP (Transmission Control Protocol)** - A core protocol of the Internet protocol suite.
- **RSS (Really Simple Syndication)** - A web feed format.
- **TOML (Tom's Obvious, Minimal Language)** - A configuration file format.
- **GitHub Actions** - A CI/CD platform for automating software workflows.
- **Rust** - A programming language used for developing the RSS reader.
- **Python** - A programming language often used with AI.
- **Assembly Language** - A low-level programming language.
- **Common Lisp** - A programming language.
- **Nix** - A package manager and system configuration tool.
- **Sway** - A tiling Wayland compositor.
- **Vitamins** - Mentioned in relation to health and longevity.
- **Magnesium** - A mineral discussed for its health benefits.
- **Vitamin D** - A vitamin discussed for its health benefits.
- **Vitamin K2** - A vitamin discussed for its health benefits.
- **Ketogenic Diet** - A diet discussed for its health benefits.
- **AI Hallucination** - The generation of false or nonsensical information by AI systems.
- **Code Monkey** - A reference to a song by Jonathan Coulton.

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This content is a personally curated review and synopsis derived from the original podcast episode.