Trail of Bits

Trail of Bits

Cybersecurity research, auditing, and consulting

Overview

Trail of Bits is a cybersecurity research and consulting firm that helps technology, defense, finance, and blockchain clients improve security through high-assurance audits, engineering, and advisory work. Its services cover threat modeling, reverse engineering, static and dynamic analysis, fuzzing, and cryptography, all informed by real-world attacker perspectives. The company stands out by keeping senior researchers on every client engagement, contributing to more than 100 open-source security tools, and pursuing public research alongside client work. Its blockchain focus includes audits for Ethereum 2.0, Uniswap, and Zcash, and its broader mission is to raise the security bar for complex software and build trusted audit practices for top organizations and governments.

About Trail of Bits

Simplify's Rating
Why Trail of Bits is rated
B-
Rated B on Competitive Edge
Rated B on Growth Potential
Rated C on Differentiation

Industries

Cybersecurity

Crypto & Web3

AI & Machine Learning

Company Size

51-200

Company Stage

N/A

Total Funding

$15M

Headquarters

New York City, New York

Founded

2012

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Simplify's Take

What believers are saying

  • July 13, 2026 Rust Testing Handbook and rust-review deepen demand from Rust teams.
  • June 30, 2026 cryptography-48 shipped ML-KEM and ML-DSA into Python.
  • 2025 ARPA-H awarded Trail of Bits up to $2 million for defensive optimization.

What critics are saying

  • OpenAI and Trail of Bits are productizing security research, compressing consulting pricing by 2027.
  • Patch the Planet's public findings invite copycat attacks against Python, Go, and cURL.
  • If AI security tooling commoditizes, Trail of Bits loses its premium differentiation and margins.

What makes Trail of Bits unique

  • Trail of Bits pairs senior researchers with client work, eliminating a junior bench.
  • Patch the Planet with OpenAI launched June 22, 2026, validating AI security at scale.
  • Its open-source tools and research moat includes Slither, Echidna, Manticore, and pyca/cryptography work.

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Funding

Total Funding

$15M

Above

Industry Average

Funded Over

7 Rounds

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Benefits

Health Insurance

Dental Insurance

Vision Insurance

Disability Insurance

Life Insurance

401(k) Company Match

Paid Vacation

Parental Leave

Relocation Assistance

Home Office Stipend

Professional Development Budget

Company Social Events

Growth & Insights and Company News

Headcount

6 month growth

-2%

1 year growth

-2%

2 year growth

-4%
Trail of Bits
Jul 13th, 2026
Rust-proof your code with our new Testing Handbook chapter.

Rust-proof your code with its new Testing Handbook chapter. July 13, 2026 Trail of Bits Inc. has added a new chapter to its Testing Handbook: a comprehensive guide to security testing Rust programs. This chapter covers the tools and techniques Trail of Bits Inc. use at Trail of Bits to validate the security of Rust programs and systems. fn main {(|f:&dyn Fn(u128)->Box< dyn Iterator<Item= char>+'static>|f(*[&( 0x7B736D70683F73u128<<64| 0x7A6A6D7C3F7A667D),&(0x7B736Du128 <<64|0x70683F7073737A77)][((std::hint:: black_box(0.0f64)/0.0).to_bits>>63)as usize]) .for_each(|c|print!("{c}")))(Box::leak(Box::new(|n: u128|Box::new(std::iter::successors(Some(n),|&n|Some(n>>8) ).take_while(|&n|n>0).map(|n|((n as u8)^0x1F)as char))as _)))} What's in the chapter. The chapter starts with a security overview of what Rust's guarantees do and don't cover, including underappreciated issues like unwind safety, nondeterminism, and arithmetic errors. This leads into an overview of dynamic analysis, which covers a range of boosters for unit tests, how to use Miri to detect undefined behavior, property testing with proptest, coverage measurement, and mutation testing. The static analysis section then covers Clippy in depth, including a list of its favorite lints. Beyond tooling, the chapter also covers what Trail of Bits Inc. has learned from auditing Rust codebases directly. Its gotchas and footguns checklist is a great reference for manual code reviews, and will help you find subtle issues like a & b == c having different operator precedence than in C. The memory zeroization section offers three solutions to the tricky problem of guaranteeing that secrets are erased from memory. Finally, the specialized testing sections cover tools like Kani (a model checker), and the supply chain section covers the full toolchain for vetting dependencies. Still oxidizing. Trail of Bits Inc. has also released rust-review, a Claude Code plugin for automated Rust security reviews. Co-built with Aptos Labs, it targets over a dozen bug classes, from memory safety and concurrency hazards to FFI pitfalls and async cancellation issues. It's a fast way to catch security issues in a Rust codebase before they make it to audit. Its goal is to keep the handbook current as the Rust ecosystem evolves. If your favorite tool or gotcha isn't covered, submit a PR. And if you need help securing your Rust systems, contact Trail of Bits Inc..

Trail of Bits
Jun 30th, 2026
Shipping post-quantum cryptography to Python.

Shipping post-quantum cryptography to Python. June 30, 2026 Post-quantum cryptography is now one pip-install away for the entire Python ecosystem. With funding from the Sovereign Tech Agency, Trail of Bits Inc. implemented support for ML-KEM, the NIST-standard key-establishment primitive, and ML-DSA, the NIST-standard digital-signature primitive, in pyca/cryptography. On June 22, 2026, the White House ordered the U.S. government to accelerate its transition to post-quantum cryptography. The order says large-scale quantum computers, especially in adversarial hands, will threaten widely used cryptographic systems, and that attackers may already be collecting encrypted data now so they can decrypt it later. It also sets concrete migration deadlines: high-value and high-impact federal systems must use post-quantum key establishment by December 31, 2030, and post-quantum digital signatures by December 31, 2031. And even if you don't care about quantum resistance, that's not a problem because quantum resistance isn't the main benefit of post-quantum crypto. That transition cannot happen only at the policy layer. Every application that signs packages, validates certificates, establishes secure channels, or protects long-lived secrets depends on cryptographic libraries. If those libraries do not expose post-quantum algorithms, the software stack cannot migrate. Almost every Python program that touches cryptography goes through pyca/cryptography. It's currently the eleventh most-downloaded package on PyPI, pulling 1.2 billion downloads in the last month alone. The pyca/cryptography package handles the cryptographic operations of projects like Ansible, Certbot (the Let's Encrypt client), Apache Airflow, paramiko (the Python-only SSH client), and many others. If pyca/cryptography doesn't ship post-quantum primitives, the Python ecosystem can't begin to migrate. Post-quantum support is now one pip install away. As of cryptography>=48, support for post quantum algorithms is just a pip install away. The version 48 release includes its Rust bindings for ML-KEM and ML-DSA, the cross binding API and tests, and support for AWS-LC as a cryptographic backend. It also includes work from pyca/cryptography's maintainers to support the other cryptographic backends. Sadly, this is not enough for a post-quantum migration drop-in swap. These primitives have different size, performance, and integration tradeoffs than the classical algorithms they replace. PQ algorithm tradeoffs. Post-quantum primitives keep the same security strength, but they change the size of the data on the wire. Public keys, signatures, and ciphertexts are often 1-2 orders of magnitude larger than the classical values they replace. The operations are also more complex and therefore slower, but on modern hardware they are still imperceptible for regular use, and are likely to get faster with improved hardware and algorithms. For signatures, here's how the classical primitive (Ed25519) compares to its post-quantum equivalent (ML-DSA-65): | Algorithm | Public key | Private key | Output | | Ed25519 | 32 B | 32 B | 64 B sig | | ML-DSA-65 | 1,952 B | 32 B | 3,309 B sig | And for key exchange and encryption, here's how X25519 compares to its post-quantum equivalent (ML-KEM-768): | Algorithm | Public key | Private key | Output | | X25519 | 32 B | 32 B | 32 B shared | | ML-KEM-768 | 1,184 B | 64 B | 1,088 B ciphertext | If you maintain a protocol or wire format that hardcodes Ed25519-sized signatures or X25519-sized public keys, the post-quantum migration involves more than a primitive swap. The surrounding fields, length prefixes, and chunking assumptions need to grow with it. Using ML-DSA (FIPS 204): Quantum-resistant signatures. ML-DSA is the lattice-based signature scheme that replaces RSA, ECDSA, and Ed25519. The Python API mirrors the existing asymmetric primitives: Using ML-KEM (FIPS 203): Key encapsulation for the post-quantum era. ML-KEM is a key encapsulation mechanism (KEM) for establishing shared secrets. The construction is different, though. ML-KEM is a key encapsulation mechanism, not a Diffie-Hellman exchange. Instead of both parties combining key shares to derive a shared secret, one party encapsulates a fresh shared secret to the receiver's public key, and the receiver decapsulates it with the matching private key. These operations allow both parties to exchange a secret but in a manner fundamentally different from Diffie-Hellman, and resistant to quantum factoring attacks. The road ahead: SLH-DSA and protocol integration. Two areas are still in progress: a third NIST standard, and the work of integrating these primitives into real protocols. SLH-DSA. SLH-DSA (FIPS 205) is NIST's hash-based digital signature standard. Like ML-DSA, it is meant to replace classical signature schemes such as RSA, ECDSA, and Ed25519. Its tradeoff is different: SLH-DSA has very large signatures and slow signing, but it relies only on the security properties of hash functions, which have been studied for decades. That makes it a conservative backstop if future cryptanalysis weakens lattice-based signatures. SLH-DSA is not supported in pyca/cryptography 48, but Trail of Bits Inc. has started working on it. Post-quantum in protocols. Primitives are the foundation, but the post-quantum migration will be complete only when protocols use the post-quantum resistant algorithms. You're unlikely to use PQ algorithms directly in tools like Certbot or Ansible until common protocols add support for them. While well-designed to replace existing implementations, algorithm changes require cautious development, testing, and auditing. Trail of Bits Inc. is actively working on helping maintainers integrate PQ algorithms into applications. Acknowledgments. This work was funded by the Sovereign Tech Agency, whose mission is to support the open-source infrastructure that public digital systems depend on. Trail of Bits Inc. is also indebted to pyca/cryptography's maintainers, Paul Kehrer and Alex Gaynor, who offered constant feedback and review throughout the development process, and continue to steward this critical piece of open-source software.

Quantum Aura
Jun 29th, 2026
OpenAI launches ai-driven effort to patch open-source security flaws.

OpenAI launches ai-driven effort to patch open-source security flaws. OpenAI has teamed up with cybersecurity firm Trail of Bits on a new initiative called Patch the Planet, aimed at using AI to uncover and fix vulnerabilities in widely used open-source software. The program comes as enterprises face growing exposure from flaws buried deep in the software supply chain. Patch the Planet combines AI-assisted vulnerability research with human review so that security findings can be turned into validated fixes and disclosed through the normal project channels. The first wave of participants includes major infrastructure projects such as Python, Go, cURL, Sigstore, NATS Server, aiohttp, freenginx, pyca/cryptography, and python.org. How the program works. OpenAI says the process begins by working with maintainers to identify where support is most needed. Researchers then look for possible vulnerabilities, confirm real issues, write or improve patches, test the fixes, and coordinate disclosure. The effort uses OpenAI's models and Codex Security to analyze code and propose remediation steps. Trail of Bits engineers then review the results before anything is sent to maintainers, which is meant to cut down on false positives and duplicate reports. OpenAI is also working with HackerOne and Calif to help with triage, disclosure, and future discovery work. According to OpenAI, the program has already surfaced hundreds of security issues and merged dozens of patches, with more fixes still moving through coordinated disclosure. The company also says the project has produced tools for fuzzing, historical CVE analysis, and differential testing, along with systems to suppress inaccurate findings before patches are generated. Why it matters. The effort arrives in the wake of major open-source incidents such as Log4Shell and the XZ Utils backdoor, both of which showed how quickly a flaw in a shared component can spread across enterprise systems. OpenAI's bet is that AI can help security teams move faster, but analysts say the real value depends on whether organizations treat AI-assisted research as one part of a broader supply-chain security program. Forrester principal analyst Biswajeet Mahapatra said the biggest advantage is speed: AI can accelerate finding, validating, patching, testing, and documenting issues, while human reviewers filter out bad signals before maintainers are overwhelmed. But, he added, the need for expert judgment does not disappear - it shifts to triage, exploitability analysis, patch safety, disclosure timing, and production rollout. Governance comes first. Security experts warn that enterprises should establish strong guardrails before plugging AI-assisted vulnerability research into their workflows. Open-source cybersecurity architect Devashri Datta said CISOs should require a "Safety Relevance Layer" that forces AI-generated findings through automated verification, dynamic proof-of-concept validation, and aggressive false-positive filtering before a human analyst ever sees them. Datta also stressed that disclosure needs to be tightly controlled, especially when vulnerabilities are found in third-party code the enterprise does not own. Teams should already have escalation paths, notification timelines, and role assignments defined before a confirmed issue is discovered. In her view, ad hoc disclosure in an AI-heavy workflow is not just a process weakness - it is a liability. Moving toward continuous exposure reduction. Analysts say AI-assisted research could push organizations away from periodic patch cycles and toward more continuous risk management. If variant analysis and differential testing can shrink from weeks to days, security teams will need faster ways to judge which findings actually matter in their environment. That also means generic CVSS scores will no longer be enough on their own. Findings will need to be evaluated based on the affected system, its business importance, runtime exposure, and the likelihood of exploitation. Datta says enterprise SBOM and VEX programs will need to evolve from static compliance artifacts into live, machine-readable data sources. Mahapatra agrees that vulnerability management will increasingly need to account for software ownership, supplier response, and business impact. He argues that security teams should move from periodic vulnerability handling to continuous exposure reduction, with SBOMs tied to runtime exposure and patch decisions guided by asset criticality, exploitability, compensating controls, and business risk.

Security Arsenal
Jun 22nd, 2026
Patch the Planet: managing the ai-driven vulnerability surge in open source.

Patch the Planet: managing the ai-driven vulnerability surge in open source. Security Arsenal Team June 22, 2026 On June 22, 2026, Trail of Bits, in partnership with OpenAI's Daybreak initiative, unveiled "Patch the Planet." This collaboration clears the schedules of dozens of engineers to leverage the advanced reasoning capabilities of the frontier model GPT-5.5-Cyber against critical open-source targets. The initial results are staggering: hundreds of bugs discovered, 64 pull requests submitted, and 51 issues filed across just 19 projects in the first week. For defenders, this initiative signals a pivotal shift in how Security Arsenal, LLC identify and remediate vulnerabilities in the software supply chain. Technical analysis. While the specific vulnerabilities uncovered are currently undergoing coordinated disclosure, the technical significance lies in the methodology and the tooling involved. The "Patch the Planet" initiative addresses a critical bottleneck in modern vulnerability management: the signal-to-noise ratio of AI-derived security findings. The AI noise problem. Frontier models like GPT-5.5-Cyber excel at static analysis and pattern recognition, capable of producing a "firehose" of potential security findings. However, these models are prone to hallucinations - flagging code patterns as vulnerabilities that are theoretically exploitable but practically irrelevant or logically impossible. For open-source maintainers who are often volunteers or stretched thin, sifting through hundreds of plausible-sounding false positives is unsustainable. It leads to alert fatigue and can cause critical issues to be lost in the noise. The human-in-the-loop advantage. This initiative differentiates itself through expert orchestration. Instead of dumping raw AI output onto maintainers, Trail of Bits engineers act as a sophisticated filter layer. They validate the GPT-5.5-Cyber findings, stripping away false positives and ensuring that only actionable, verified vulnerabilities reach the maintainers via pull requests and issue trackers. This human-ai symbiosis allows for the scale of automation without sacrificing the precision required for effective security patching. Impact on the supply chain. The focus on open-source targets is of paramount concern. The 19 projects currently under review represent foundational components likely utilized by thousands of downstream applications. A single vulnerability in a widely used library can have a blast radius affecting millions of systems. The discovery of "hundreds of bugs" suggests that its current reliance on open source may be built on a more precarious foundation than previously understood, necessitating a more aggressive approach to dependency hygiene. Executive takeaways. Given that this news item describes a proactive security initiative rather than a specific active exploitation campaign (CVE), the following defensive recommendations focus on organizational readiness and supply chain resilience: * Prepare for High-Velocity Patching: As initiatives like "Patch the Planet" scale, the volume of CVEs assigned to open-source libraries will increase. Your organization must move from reactive patching to automated dependency update workflows. If you are manually updating requirements.txt or package., you are already falling behind. * Establish a Validation Pipeline for AI Findings: As your team likely adopts AI security tools (AI-DAST, AI-Static Analysis), do not feed AI-generated alerts directly into your ticketing system. Implement a tiered triage process where senior engineers or automated validation logic verifies the exploitability of the finding before developer time is consumed. * Aggressive SBOM Deployment: You cannot patch what you do not know you have. The Software Bill of Materials (SBOM) is no longer optional. With hundreds of bugs looming in unnamed projects, an accurate, up-to-date SBOM is the only way to rapidly determine your exposure once the coordinated disclosure lifts. * Support the Maintainer Ecosystem: The bottleneck in open-source security is human capital. If your organization relies heavily on specific open-source projects, consider allocating budget or engineering hours to support the maintainers. The "Patch the Planet" initiative highlights that maintainers need help managing the influx of security data; your organization can be part of the solution rather than just a consumer. Remediation. While specific CVEs and patch versions are pending disclosure, defenders should take the following steps to harden their environment against the inevitable wave of updates stemming from this initiative: * Monitor Official Channels: actively monitor the Trail of Bits blog and the repositories of your critical dependencies for security advisories related to "Patch the Planet." * Audit Your Dependencies: Run a dependency scan (e.g., using npm audit, pip-audit, or commercial SCA tools) to catalog your current versions. When the 64 pull requests are merged and releases are tagged, you will need this baseline to identify which assets require updating. * Test Environments: Ensure your staging environments are fully representative of production. With a potential surge of patches incoming, regression testing will be critical to ensure that security fixes do not break functionality. Related resources. cve zero-day patch-tuesday exploit vulnerability-disclosure ai-security open-source supply-chain Is your security operations ready? Get a free SOC assessment or see how AlertMonitor cuts through alert noise with automated triage.

Simply Secure Group
Jun 22nd, 2026
OpenAI releases gpt5.5cyber with full automation for vulnerability detection and patching.

OpenAI releases gpt5.5cyber with full automation for vulnerability detection and patching. June 22, 2026 OpenAI has officially launched the full version of GPT-5.5-Cyber, a specialized AI model engineered for advanced vulnerability detection, patch generation, and automated remediation at machine speed. The release is part of OpenAI's broader Daybreak initiative, which aims to democratize defensive cybersecurity capabilities for trusted organizations worldwide. GPT-5.5-Cyber delivers state-of-the-art results across three major cybersecurity evaluation benchmarks: * CyberGym: 85.6% (vs. 81.8% for GPT-5.5), the highest single-model score recorded. * ExploitGym: 39.5% (vs. 25.95% for GPT-5.5), testing exploit generation from known vulnerabilities. * SEC-bench Pro: 69.8% (vs. 63.1% for GPT-5.5), evaluating long-horizon vulnerability discovery across complex software targets. The model can navigate large codebases, trace attack paths, validate exploitability, generate targeted patches, and produce remediation evidence all within a single automated workflow. Codex Security plugin updated. Alongside the model release, OpenAI has updated the Codex Security plugin, now capable of deep codebase scanning with automated patch generation. Since launching in research preview in March 2026, Codex Security has: * Scanned over 30 million commits across more than 30,000 codebases * Processed over 70,000 manually verified fixes * Automatically resolved over 500,000 findings The plugin integrates directly into developer workflows, supporting SARIF exports, CodeQL queries, and existing vulnerability management pipelines. It generates severity-rated reports with affected code locations, attack path tracing, and codebase-specific patches for human review. OpenAI launched Patch the Planet, a collaborative initiative co-founded with Trail of Bits and partnered with HackerOne and Calif, to address the critical vulnerability remediation gap in open-source software. More than 30 open-source projects have committed to participate, including: * cURL, Go, Python, Sigstore, and pyca/cryptography An initial five-day sprint across multiple projects surfaced hundreds of issues, merged dozens of patches, and built reusable fuzzing and variant-analysis workflows. Participating projects receive ChatGPT Pro, conditional Codex Security access, and API credits. GPT-5.5-Cyber is distributed exclusively through a limited release to verified, trusted defenders. It is not available for general use. OpenAI has confirmed Trusted Access for Cyber partnerships with Australia, Canada, France, Germany, Japan, South Korea, and EU institutions, including ENISA. OpenAI coordinated pre-deployment testing with the Center for AI Standards and Innovation (CAISI) and worked with the Office of the National Cyber Director (ONCD) on the implementation of the June 2026 Executive Order on AI security. For most organizations, GPT-5.5 with Trusted Access for Cyber and Codex Security remains the recommended entry point, with GPT-5.5-Cyber reserved for defenders requiring the highest capability tier with enhanced monitoring and scoped controls. OpenAI's announcement signals a fundamental shift in the cybersecurity threat model. The historical bottleneck of finding vulnerabilities has given way to a new challenge: patching them at scale. With Daybreak unifying frontier AI models, Codex Security workflows, open-source partnerships, and critical infrastructure collaboration, OpenAI is positioning AI-driven remediation, not just detection, as the next frontier in cyber defense. Follow Simply Secure Group on Google News, LinkedIn, and X to Get More Instant Updates.

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