Nearly 20 years ago, Anonym.OS emerged as a revolutionary privacy tool—a bootable Live CD built on OpenBSD that made anonymous browsing as simple as rebooting your computer. Created by the kaos.theory security research group, it provided encryption, anonymity, and secure communications in an era when most people didn’t realize they needed it.
After debuting at ShmooCon 2006 to a packed audience (including Tor’s inventors in the front row) and earning a 12-week feature on Wired.com, Anonym.OS quickly became a cultural touchstone for online privacy. Downloaded hundreds of thousands of times, it demonstrated both the demand for privacy and the debate over how accessible anonymity should be.
Today, the team behind Anonym.OS is back with Anonymity Reimagined—a modern, actionable guide to reclaiming your privacy in a world of surveillance, tracking, and data exploitation. Here’s the story of how Anonym.OS changed online anonymity—and what’s next.
What Is Anonym.OS? The OpenBSD Tool That Made Anonymity Easy
In late 2003, I began experimenting with Tor, a then-new project developed by U.S. Naval Research Laboratory mathematician Paul Syverson and computer scientists Roger Dingledine and Nick Mathewson. Initially called The Onion Routing Project, it was designed to protect American intelligence communications online. The acronym “Tor” was later adopted to reflect its underlying technology.
By early 2004, Tor was still in its infancy and faced performance limitations that made real-world use challenging. It was these limitations—and the rising need for practical, accessible anonymity tools—that sparked the idea for what would eventually become Anonym.OS.
How Anonym.OS Was Born: From Tor’s Limitations to ShmooCon Fame
On February 5, 2005, I attended the first-ever ShmooCon in Washington, D.C., where I met Roger Dingledine after his talk, “Low-Latency Anonymizing Networks.” I praised his work and expressed frustrations about Tor’s usability and speed—issues that would directly inform the design goals of Anonym.OS.
A month later, on March 11, 2005, I gave a presentation at Interz0ne 4, an Atlanta hacker conference that hosted notable speakers including Caleb Sima, Ofir Arkin, Ron Gula, and Simple Nomad.
My talk focused on building hardened, transportable systems for encrypting and anonymizing network traffic:
Building an Anonym.OS (aka The H.O.T.S.E.A.T.: a Hardened, Optimized Transportable System for Encrypting and Anonymizing Traffic)
This talk will discuss the process of hardening and reconfiguring your [laptop/desktop] to ensure that all externally-initiated communications are dropped/denied, and that all locally-initiated traffic is encrypted and/or anonymized -- optimally both -- from your machine to its final destination.
Through this process, a host machine can be introduced to an arbitrary network (hotel broadband, WiFi hotspot, client network, etc.) without leaving discernible fingerprints or telltale footprints. The talk will focus primarily on Linux and BSD systems (incl. Mac OS X), though there will be discussion about accomplishing the same goals, to the greatest degree possible, on Windows as well.
Before delivering the presentation, I pulled together a team of like-minded hackers and security researchers, founding the group kaos.theory/security.research under the motto: “security research, in fractal detail.”
Key capabilities outlined in this talk included:
- Dropping all externally initiated communications.
- Encrypting or anonymizing locally initiated traffic.
- Creating pseudonymous systems that left no traceable fingerprints, even on hostile networks.
Building Anonym.OS: From Concept to Execution (2005)
Following the Interz0ne talk, I reached out to Roger Dingledine again in April 2005 to share my progress and ideas for a LiveCD implementation. By April 12, work on what would become Anonym.OS officially began.
kaos.theory member Chris Elmore (3lm0r3) suggested building on OpenBSD—despite no existing OpenBSD LiveCDs at the time. Inspired by the challenge, we set out to create not only the first fully functional OpenBSD LiveCD, but one focused explicitly on security, privacy, and anonymity.
By October 2005, the project was approved on SourceForge, and we submitted a proposal to ShmooCon with the following abstract:
Anonym.OS: Security and Privacy, Everywhere You Go
Privacy and anonymity are hard to come by these days. What's worse, many if not most, of the world's network users don't have the slightest idea of the levels of monitoring to which they are subjected, much less the proper chain of steps necessary to strengthen their communications channels. While there are applications and systems that provide heightened anonymity and confidentiality to users, all require user-knowledge of configuration and proper systems administration techniques. The tiniest error in setting up any of the myriad tools available can lead to disaster. To fill this void, kaos.theory has created the Anonym.OS OpenBSD LiveCD.
The Anonym.OS LiveCD project seeks to accomplish three goals; first, to provide the user a secure, silent system that can be attached to any network without leaving traceable footprints; secondly, to integrate encryption, privacy, and "anonymizing" applications in a seamless fashion; lastly, to offer standard, graphical tools for web, news, mail, and chat that utilize enhanced privacy and anonymity in an easy-to-use, secure, and portable environment. To achieve these goals, kaos.theory has made extensive use of OpenBSD, pf, tor, and anonymizing proxies.
Anonym.OS provides strong privacy, anonymity, and security in a package suitable to give to your grandmother for use at her local $tar6ucks. You know, if your grandmother has something to hide…
ShmooCon II: The Debut and Media Storm (2006)
On January 14, 2006, we unveiled Anonym.OS at the second ShmooCon to a packed audience.
Tor creators Paul Syverson (above right) and Roger Dingledine (above left) sat front-row for the talk. and got some of the first pressed copies of the live CD at the end of the presentation. That same day, Wired published Quinn Norton’s feature article, “Anonymity on a Disc,” on their homepage, which remained featured for over twelve weeks.
The article sparked widespread attention—and controversy. While it critiqued the project, it also drove massive downloads—over 190,000 in the first 36 hours.
The Impact of Anonym.OS — Media Coverage and Public Reaction
The project received significant attention from various media outlets and was featured on platforms like Slashdot, Hackaday, and Bruce Schneier’s blog.
The Register described Anonym.OS as “a high level of anonymity [and] a welcome relief.” Additionally, it was later showcased on Hak5 by Mubix, further increasing its reach and visibility.
- Wired - “Anonymity on a Disc”
- Slashdot – “Anonym.OS: A Boon for Privacy Geeks”
- Hackaday – “ShmooCon 2006: Anonym.OS Security & Privacy Everywhere You Go”
- Schneier on Security – Praising the project as a step toward democratizing anonymity tools.
- Ars Technica – “OpenBSD LiveCD Focuses on Anonymity and Privacy”
- The Register – Highlighted Anonym.OS as a tool for privacy enthusiasts.
- Hak5 – Featured a segment with Mubix discussing its functionality.
Notable Quotes
- “Anonym.OS makes anonymity as simple as popping in a CD and rebooting.” – Wired
- “It’s a welcome relief—a high level of anonymity in an easy-to-use package.” – The Register
The Rebuttal
kaos.theory member Gavin Mead (atlas) responded to Wired’s criticisms with a detailed rebuttal, defending the project’s goals and addressing legitimate challenges, such as scaling anonymity against censorship in countries like China. (Notably, none of the individuals interviewed for the article — aside from the creators — had actually seen or used Anonym.OS firsthand. As a result, their comments were purely speculative and uninformed by the system’s actual functionality, design, and capabilities.)
We're flattered and honored to have made a splash large enough to even need to write a response. Clearly privacy is a big issue on a lot of minds right now.
"Rebooting isn't an option for some." - Ethan Zuckerman
This is an excellent point. We have USB key-chain usage built into the roadmap.
For now, we need as many people who can reboot to use the Anonym.OS and give us feedback / feature suggestions / help. Immediately after the demonstration, several great ideas were floated by audience members that hadn't even booted the CD and this type of feedback is critical to project success.
Regarding the "China Problem" (or corporate networks that break SSL / enforce true proxies) - Ethan Zuckerman
We're currently limited by the upstream connection. The roadmap addresses this in a way with plans for automated egress filtering subversion using covert channels such as ICMP and DNS. This will, of course, require an outside semi-trusted "friend" for running a relay. Watch for further developments on this from KTSR.
Use of covert channels will obviously cause problems in terms of anomaly-detecting monitoring systems. This is something that must be kept in mind when considering that the fate of people in oppressive regimes may be riding on the confidentiality (and secrecy) of their Internet use.
If you "own" the entire network (such as is the case with China), there is really no way for the downstream client to have consistent, secure, and anonymous outbound access. Ultimately, the network controller could institute a white-list only policy, denying all outbound traffic. Think China would flinch at this? Think again. They'd just ask their pals at Cisco for a hand.
“My instincts tell me that it's a very small number of people (that can use Anonym.OS). You can't really solve this problem by simplifying the interface. It's almost impossible to anticipate everything a user can do to hurt themselves." - David Del Torto
Ummm…. OK. If you are aware of privacy concerns enough to utilize a live CD (or, in the future, live USB key) strictly to protect your privacy, perhaps you're not quite so stupid as to surf immediately to www.evil-spammer-haven.com and start filling in your private details?
But even if you were that stupid, the spammer would still be unable to know your originating IP address and those sitting next to you in the mental institution wouldn't be able to sniff the traffic or know what you're doing.
Your instinct is wrong. If you show me someone who can't use Anonym.OS to surf the web, get their email, and chat on instant messenger, I'll show you a corpse.
How Anonym.OS Inspired and Shaped Modern Privacy Tools
When Anonym.OS debuted, it quickly became a go-to solution for privacy advocates, journalists, and activists seeking accessible anonymity. With hundreds of thousands of downloads, it set a new standard for user-friendly privacy tools and proved that robust security didn’t have to be complicated.
Although active development of Anonym.OS ceased after its final Beta 4 release in 2006, its core principles—accessibility, security, and ease of use—left a lasting imprint on the world of privacy-focused operating systems. One of the most well-known successors is Tails (The Amnesic Incognito Live System), a Debian-based OS designed to preserve anonymity, which drew inspiration from early projects like Incognito and Anonym.OS.
The Next Generation of Privacy-Focused Operating Systems
While Anonym.OS may have paved the way, it wasn’t the end of the road. In the years that followed, several groundbreaking privacy tools emerged, each addressing evolving security challenges while staying true to the mission of empowering users with accessible anonymity. Among the most notable are:
- Tails OS – A live operating system that runs from a USB stick, enabling users to browse anonymously and leave no trace, now an official part of the Tor Project.
- Qubes OS – A security-focused OS that uses compartmentalization to isolate threats and safeguard sensitive information.
- Whonix – A privacy-enhancing OS that routes all traffic through the Tor network to provide strong anonymity protections.
These tools continue to evolve, carrying forward the legacy of making strong privacy protections available to those who need them most.
The Revival: Anonymity Reimagined and the Future of Privacy
The kaos.theory team continued refining ideas around anonymity and privacy, giving follow-up talks like “Becoming Jack Flack: Real-Life Cloak & Dagger” at ShmooCon 2010. This session provided a practical roadmap for anonymity across three levels—CLOAK, DAGGER, and HERMIT—addressing growing concerns about online surveillance.
What's Coming Next?
Nearly 20 years later, members of the original kaos.theory team — including Taylor Banks, Beth Banks, Adam Bregenzer, Kevin Miller, Chris Elmore, Gavin Mead, and new addition, K.C. Budd — have reunited to revisit and modernize the project.
Their latest work, Anonymity Reimagined: Protecting Privacy, Security & Freedom in an Era of Fear, was proposed for the final ShmooCon in 2024. While the talk was not accepted, the team remains committed to evolving Anonym.OS—not as a LiveCD but as a comprehensive guide to securing privacy in an era of pervasive surveillance.
Protecting Privacy, Security & Freedom in an Era of Fear
In a time of escalating scrutiny and mounting threats, in a world where digital footprints are tracked and monetized, where privacy feels like a relic of the past, and anonymity is often seen as subversive, safeguarding one’s privacy is no longer a luxury—it’s a necessity. With rising fears surrounding surveillance, political targeting, and social manipulation, reclaiming control over one’s online presence is critical for vulnerable communities, including LGBTQ+ individuals, PoC, immigrants, women, and anyone at risk.
Nearly two decades ago, we introduced Anonym.OS to empower users with tools for anonymity. Today, we return with a modern approach tailored to the needs of anyone seeking safety and resilience online. Join the original creators of Anonym.OS as we guide you through practical strategies to reclaim privacy and strengthen your online security without sacrificing modern connectivity. We’ll provide step-by-step methods and resources for scrubbing your online presence, shielding you from intrusive data brokers, and hardening devices against surveillance. Whether you seek to maintain basic discretion or achieve robust anonymity, we offer tangible solutions to protect you in an increasingly monitored world.
This is your path to staying secure, private, and anonymous in a world that targets, tracks, and manipulates you.
Anonym.OS began as an experiment to make anonymity accessible, quickly becoming a widely adopted tool and a cultural touchstone in the hacker and privacy communities.
Its legacy continues through the kaos.theory team’s efforts to empower individuals with the knowledge and tools needed to reclaim their privacy in a world that relentlessly tracks and monetizes their lives.
For those looking to revisit the project’s roots, media coverage, and code, archives remain available:
Wired: Original Article
Slashdot: Coverage
Hackaday: Feature
Schneier’s Blog: Review