Adrian Lamo

Adrian Lamo is an infamous former grey hat hacker and journalist, principally known for breaking into a series of high-security computer networks, and his subsequent arrest. Best known among these were his intrusions into The New York Times and Microsoft. He is also known for attempting to identify security flaws in computer networks of Fortune 500 companies and then notifying them of any found; while still illegal in many places without permission, this can be seen as a form of unsolicited penetration testing. Dubbed the "homeless hacker" for his transient lifestyle, Lamo spent most of his travels couch-surfing, squatting in abandoned buildings and travelling to Internet cafes, libraries and universities to investigate networks, and sometimes exploit security holes. Despite performing authorized and unauthorized vulnerability assessment for several large, high-profile entities, Lamo refused to accept payment for his services. In the past, his lifestyle allowed him to travel up and down the coasts of the United States, often by coach, carrying all necessary possessions in a backpack.

Adrian Lamo is perhaps best known for breaking into The New York Times internal computer network in February 2002, adding his name to confidential databases of expert sources, and using the paper's LexisNexis account to conduct research on high-profile subjects, although his first published activities involved operating AOL watchdog site Inside-AOL.com.

in 2004, Lamo was sentenced to six months' detention at his parents' home plus two years probation, and was ordered to pay roughly $65,000 in restitution. He was convicted of compromising security at The New York Times and Microsoft, and is alleged to have admitted to exploiting security weaknesses at Excite@Home, Yahoo!, Microsoft, MCI WorldCom, Ameritech, Cingular and has allegedly violated network security at AOL Time Warner, Bank of America, Citigroup, McDonald's and Sun Microsystems. Companies sometimes use proxies to allow their employees access to the internet, without giving the internet access to their internal network. However, when these proxies are improperly configured, they can allow access to the company's internal network. Lamo often exploited this, sometimes using a tool called ProxyHunter.

Critics have repeatedly labelled Lamo as a publicity seeker or common criminal, claims that he has refused to publicly refute. When challenged for a response to allegations that he was glamorizing crime for the sake of publicity, his response was "Anything I could say about my person or my actions would only cheapen what they have to say for themselves." When approached for comment during his criminal case, Lamo would frequently frustrate reporters with non sequiturs such as "Faith manages" and "It was a beautiful day."

At his sentencing, Lamo expressed remorse for harm he had caused through his intrusions, with the court record quoting him as adding "I want to answer for what I have done and do better with my life."
As of January 16, 2007, Lamo's probation was terminated, ending a three-year period during which the U.S. District Court's ruling prevented him from exercising certain freedoms, including the ability to employ any privacy protection software, travel outside certain established boundaries, or socialize with security researchers.

Can You Hack It?, a documentary covering Lamo's life and times, is slated for release under the care of Trigger Street Productions. Directed by Sam Bozzo, it features Apple Computer co-founder Steve Wozniak, TechTV personality Leo Laporte, and narration by actor Kevin Spacey. The film explores the practical and ethical themes of modern computer hacking, intertwining Lamo's story with those of controversial figures throughout history.