AI Accelerates Development While Code Signing Becomes Costlier - Episode Hero Image

AI Accelerates Development While Code Signing Becomes Costlier

Security Now (Audio) · · Listen to Original Episode →
Original Title:

TL;DR

  • The shift to short-lived, expensive code signing certificates, particularly Microsoft's three-day certificates, represents a significant cost increase and complexity for developers, potentially driven by revenue generation rather than solely security enhancements.
  • Microsoft's Azure Trusted Signing service offers a more affordable code signing solution compared to traditional vendors, but requires navigating a complex Azure ecosystem and has a steep learning curve for setup.
  • The increasing cost and complexity of code signing certificates, coupled with shorter lifetimes, could lead to software updates becoming more burdensome and potentially impact the long-term validity of older, unmaintained software.
  • Time-stamping authorities (TSAs) are crucial for code signing, as they provide an unforgeable timestamp at the moment of signing, ensuring the code's integrity and the signer's identity remain verifiable even after the signing certificate expires.
  • The rise of AI coding assistants like Claude Code is dramatically accelerating development for both novice and expert programmers by automating boilerplate code generation, debugging, and even complex feature implementation, fundamentally changing the software development landscape.
  • California's new data broker opt-out law (DROP) provides a mechanism for residents to request data deletion, but requires users to submit extensive personal information, highlighting the ongoing tension between privacy and data accessibility.

Deep Dive

The proliferation of AI coding tools is fundamentally altering the software development landscape, enabling individuals without traditional coding backgrounds to create applications and accelerating the output of experienced developers. This shift, however, is occurring alongside a significant increase in the cost and complexity of code signing, driven by evolving security mandates that necessitate shorter certificate lifetimes and more stringent key management.

The implications of these concurrent trends are far-reaching. The democratization of app development through AI lowers the barrier to entry for innovation, potentially leading to a surge in custom software solutions tailored to specific needs. Yet, this accessibility is counterbalanced by the increasing financial and administrative burden of code signing. As certificate authorities impose stricter rules, like the mandatory use of Hardware Security Modules (HSMs) or cloud-based signing services, and shorten certificate validity periods to mere days, developers face escalating costs and a more complex compliance process. This creates a tension between the ease of AI-assisted development and the friction of ensuring the authenticity and integrity of that code. Furthermore, the shift towards shorter-lived, cloud-served certificates, while intended to mitigate risks from compromised keys, necessitates robust time-stamping mechanisms to maintain the long-term trust in signed code and risks creating new vulnerabilities if not implemented correctly. The industry is thus navigating a period where building software is becoming easier and more accessible, but proving its trustworthiness is becoming more expensive and convoluted.

Action Items

  • Audit code signing certificates: Verify expiration dates and timestamping mechanisms for 5-10 critical internal applications.
  • Implement automated code signing: Integrate timestamping authority (TSA) services into CI/CD pipelines for all new software releases.
  • Evaluate Azure Trusted Signing: Compare pricing and setup complexity against current code signing solutions for 3-5 projects.
  • Establish certificate lifecycle management: Draft a policy for managing code signing certificate renewals and expirations, including a 2-year review cycle.

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."

This quote from Rick Stroll highlights a significant shift in code signing practices. Stroll explains that modern security mandates require certificates to be managed by certified online authorities or stored in specific hardware modules, preventing keys from being easily copied or used elsewhere. This change aims to enhance security by limiting the accessibility of private keys.

"The validation rules for businesses have not changed and you would think most of the expense is all in that but this isn't about security it's about gatekeeping and just one more hurdle for a small business to have to jump over."

Rick Stroll expresses a critical perspective on the rising costs and complexities of code signing. He argues that the increased expense is not primarily driven by enhanced security measures but rather by a deliberate effort to create barriers for smaller businesses. Stroll suggests that the current system functions more as a form of gatekeeping than a genuine security enhancement.

"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."

Steve Gibson introduces the core topic of the podcast, explaining Microsoft's approach to code signing certificates. Gibson notes that Microsoft is issuing certificates with extremely short lifespans of only three days. This strategy, according to Gibson, is intended to mitigate risks associated with compromised certificates by ensuring they quickly become invalid.

"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 recounts his experience setting up Microsoft's Azure Trusted Signing service. Stroll describes the process as unexpectedly difficult and time-consuming, taking nearly a full workday. He attributes this complexity to confusing terminology and challenging dependency management within the Azure ecosystem.

"The signing certificate's validity window from the not valid before to the not valid after times is enforced by an un spoofable timestamp provided in real time on the fly at the moment of signing by a third party time stamping service whose certificate whose own certificate their public certificate is also attached."

Steve Gibson explains the role of a Time Stamp Authority (TSA) in code signing. Gibson clarifies that a TSA provides an unforgeable timestamp at the moment of signing, which is then attached to the code along with the signer's certificate. This timestamp ensures that the code's validity is permanently anchored to the time it was signed, regardless of the signing certificate's subsequent expiration.

"The brilliance of bricklin's spreadsheet was that it was a programming language it was visicalc allowed you to to put numbers in and do with them what you wanted and you know so it was a type of programming language and you know and there are some databases that have been like that through the years where you know they they were really they really helped you get the job done."

Leo Laporte reflects on the historical significance of early software like VisiCalc. Laporte emphasizes that VisiCalc was more than just a spreadsheet; it functioned as a programming language, empowering users to manipulate data in ways that were previously impossible. He draws a parallel to certain databases that also offered similar capabilities, enabling users to achieve specific tasks.

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 a newer, updated version of "The Magnesium Miracle" with advances in clinical magnesium 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 walkthrough of setting up Microsoft Azure cloud code signing.
- **"Logitech Options+ and G Hub Mac OS Apps Break After Certificate Expires"** (Bleeping Computer) - Referenced as an example of software breaking due to an expired code signing certificate.

### People
- **Rick Stroll** - Author of a blog post on Microsoft Trusted Signing, providing insights into code signing certificate changes.
- **Andrew Ng** - Founder of DeepLearning.AI, creator of the "Build with Andrew" course on AI coding for non-coders.
- **Al Liebel** - Listener and developer who used Claude Code to build an open-source project, sharing his experience.
- **Carolyn Dean** - Author of "The Magnesium Miracle" and "Magnesium: The Missing Link to Total Health."
- **Jay Thompson** - Listener who suggested starting a certificate authority service.
- **Scott** - Listener who appreciates comments on vitamins and their impact on longevity.
- **Steve Penfold** - Listener who provided an update on the editions of "The Magnesium Miracle" book.
- **Joey Albert** - Listener who enjoyed "The Lazarus Project" series.
- **Mr. Ron** - Listener who binge-watched "The Lazarus Project" and found it outstanding.
- **Paul Thurat** - Mentioned as another user who enjoys Paint Shop Pro.
- **Jonathan Coulton** - Mentioned for his song "Code Monkey."
- **George Moro** - Mentioned in relation to his early suitcase computers and the idea of custom software.
- **John C. Dvorak** - Mentioned as someone who discussed George Moro's computers.

### Organizations & Institutions
- **Microsoft** - Mentioned in relation to Azure cloud code signing services and code signing certificate policies.
- **Amazon** - Mentioned in a phishing text message example.
- **T-Mobile** - Mentioned in a phishing text message example.
- **Apple** - Mentioned in relation to Apple Wallet, Apple messages, and the iOS built-in map app.
- **American Express** - Mentioned in relation to credit card fraud.
- **Lowe's** - Mentioned in relation to credit card fraud.
- **ThreatLocker** - Mentioned as the location for a presentation on "The Call is Coming From Inside the House."
- **California Privacy Protection Agency (Cal Privacy)** - Mentioned in relation to the data broker opt-out law (DROP).
- **Secure.login.gov** - Mentioned as a third-party vendor assisting with California residency verification for DROP.
- **DeepLearning.AI** - Publisher of "The Batch" newsletter and host of the "Build with Andrew" course.
- **Google Brain** - Co-founded by Andrew Ng.
- **Coursera** - Co-founded by Andrew Ng.
- **Baidu** - Where Andrew Ng led AI.
- **Stanford University** - Where Andrew Ng is an adjunct professor and former director of the AI lab.
- **Hoxhunt** - Sponsor of the podcast, offering a security training platform.
- **Qualcomm** - A company that uses Hoxhunt training.
- **AES** - A company that uses Hoxhunt training.
- **Nokia** - A company that uses Hoxhunt training.
- **US National Weather Service** - Mentioned for an AI-generated wind forecast map with fictitious towns.
- **HMail Server** - An open-source email server mentioned by Steve Gibson.
- **Let's Encrypt** - A provider of free TLS certificates, mentioned in the context of certificate authorities.
- **DigiCert** - A certificate authority mentioned in relation to code signing certificates.
- **Identrust** - A certificate authority mentioned in relation to bootstrapping trust for Let's Encrypt.
- **Verisign** - A certificate authority mentioned as an example of a long-lived neutral name.
- **G2** - A platform where Hoxhunt has user reviews.
- **Gartner** - Recognized Hoxhunt as a customer's choice.
- **Nokia** - A company that uses Hoxhunt training.
- **Qualcomm** - A company that uses Hoxhunt training.
- **AES** - A company that uses Hoxhunt training.

### Tools & Software
- **Claude Code** - An AI coding tool mentioned as a life-changing accelerant for development.
- **Azure Trusted Signing** - Microsoft's cloud code signing service.
- **EM Client** - An email client that Steve Gibson found to be a better user experience than Apple's native mail app.
- **VS Code** - A code editor mentioned in relation to using AI for coding.
- **GitHub Actions** - Used by Leo to build binaries for his RSS reader.
- **Sway** - A text-based window manager used by Leo for configuration.
- **Nix** - Mentioned as a potential alternative to Sway for text-based configuration.
- **Roku Channel** - Mentioned in relation to accessing advertising identifiers.
- **Global Entry** - Mentioned as a service that might use login.gov.
- **HMail Server** - An open-source email server.
- **Never 10** - A Windows executable program from GRC.
- **Paint Shop Pro** - Software mentioned as an example of perpetual license software.
- **Logitech Options+** - Logitech software that stopped working after a certificate expired.
- **Logitech G Hub** - Logitech software that stopped working after a certificate expired.

### Websites & Online Resources
- **grc.com** - Steve Gibson's website.
- **consumerdrop.privacy.ca.gov** - The website for California's data broker opt-out platform (DROP).
- **cheapsslsecurity.com** - A website where Fast SSL certificates are available.
- **buildwithandrew.deeplearning.ai** - The website hosting Andrew Ng's free course on AI coding.
- **github.com/leoreport/rss-reader** - Leo's public GitHub repository for his RSS reader.
- **awesome-claude.github.io** - A GitHub page with resources for using Claude's skills.

### Podcasts & Audio
- **Security Now Podcast** - The podcast where this discussion took place.
- **MacBreak Weekly** - A podcast where Steve Gibson discussed being fished.
- **TWIT** - The network that produces Security Now.

### Other Resources
- **Code Signing Certificates** - A primary topic of discussion, focusing on their purpose, expiration, and cost.
- **Three-Day Certificates** - A specific type of code signing certificate mentioned in relation to Microsoft Azure Trusted Signing.
- **Public Key Cryptography** - Mentioned in the context of code signing complexities.
- **FIPS 140-2 Level 2+ Compliant Hardware Security Module (HSM)** - A requirement for storing code signing keys.
- **EV (Extended Validation) Certificates** - A type of code signing certificate with stricter vetting.
- **Global Data Broker Opt-Out (DROP)** - A California law and platform for data deletion requests.
- **AI (Artificial Intelligence)** - A broad topic discussed in relation to coding, forecasting, and various tools.
- **Generative AI** - Mentioned as the technology that produced fictitious town names in a weather forecast.
- **IMAP (Internet Message Access Protocol)** - Mentioned in relation to email client issues and server crashes.
- **TCP (Transmission Control Protocol)** - Mentioned in the context of maintaining an open connection for IMAP.
- **ACME (Automated Certificate Management Environment)** - A technology associated with Let's Encrypt.
- **Time Stamp Authority (TSA)** - A trusted third party that provides verifiable timestamps for signed code.
- **Vitamins** - Mentioned as a topic Steve Gibson occasionally discusses.
- **Magnesium** - A vitamin discussed for its health benefits, including improved sleep.
- **Vitamin D** - Mentioned in relation to supplementary nutrition.
- **Vitamin K2** - Mentioned in relation to supplementary nutrition.
- **Ketogenic Way of Eating** - Mentioned in relation to supplementary nutrition.
- **The Lazarus Project** - A TV series recommended by listeners.
- **For All Mankind** - A TV series mentioned as speculative fiction about the space race.
- **Perpetual License Software** - Software for which a license is purchased once.
- **Freeware** - Software that is available at no cost.
- **Global Privacy Control (GPC)** - A browser setting to indicate privacy preferences.
- **OLED (Organic Light-Emitting Diode)** - Mentioned in relation to desired iPad hardware.
- **RSS Reader** - A text-based application developed by Leo with AI assistance.
- **Natural Language Interfaces** - Discussed as a long-standing goal for computer interaction.
- **Buffer Overflows** - A type of security vulnerability.
- **Stir Copy** - Mentioned as a function that Claude is unlikely to misuse, unlike `strcpy`.
- **MongoDB** - Mentioned in relation to its default port number and security.

---
Handpicked links, AI-assisted summaries. Human judgment, machine efficiency.
This content is a personally curated review and synopsis derived from the original podcast episode.