Appelbaum says that he tested out of high school and attended junior college briefly before he "stopped college and continued [his] education". In a wide-ranging interview with Rolling Stone magazine in 2010, Appelbaum stated that he comes from "a family of lunatics... [a]ctual, raving lunatics". He stated that his mother "is a paranoid schizophrenic" who "insisted that Jake had somehow been molested by his father while he was still in the womb". He was taken away from his mother by his aunt when he was 6. Two years later, he was placed in a children's home in Sonoma County. At age 10, his indigent father was awarded custody of him. According to him, having been introduced to computer programming by a friend's father saved his life: "The Internet is the only reason I'm alive today." Appelbaum says that he developed OCD at a young age. He has also stated that his father, who struggled with heroin addiction, has been murdered by poisoning.
Appelbaum has collaborated on several other high-profile research projects.
Appelbaum is also a photographer who has contributed still photographs to film and game projects. He exhibited his work in a solo show at NOME in 2016.
Appelbaum represented Wikileaks founder Julian Assange in a keynote address at the 2010 HOPE conference.
Appelbaum says he believes he has been under government surveillance since 2009, to the detriment of himself, his friends, and his close relations. In interviews he has stated that living in Germany has given him a sense of relief from U.S. surveillance. Appelbaum has described various aggressive surveillance events, and implies they are related to his work with WikiLeaks, to his privacy activism, and to relationships with other privacy activists, notably reporters linked to Edward Snowden. In December 2013, Appelbaum said he suspected the U.S. government of breaking into his Berlin apartment and using his computer.
While traveling, Appelbaum has been detained at airports and had his electronic equipment seized several times.
In 2015, it was revealed that Google had been forced to turn over information from his Gmail account.
In 2019, he told reporters that he had been contacted by Alexandria prosecutors about cooperating with the WikiLeaks grand jury for immunity, but had refused.
In March 2015, Appelbaum was suspended from his position at the Tor Project for ten days due to alleged incidents of harassment.
Also on 4 June, a website appeared with anonymous accounts of mistreatment by Appelbaum. On 6 June, Appelbaum issued a statement denouncing the allegations as part of a concerted strategy to damage his reputation. Security engineer Leigh Honeywell came forward on 7 June to publicly relate the website's stories with her relationship with Appelbaum, in which she described Appelbaum ignoring a safeword and becoming violent. An anonymously leaked letter that the Tor Project's human resources manager had written to Appelbaum in conjunction with his March 2015 suspension for unprofessional conduct was published on 7 June. On 15 June, Alison Macrina (the director of the Library Freedom Project) and Isis Lovecruft (a Tor developer) publicly announced that the website's anonymous accounts of sexual abuse, under the pseudonyms of "Sam" and "Forest", respectively, were their own.
On 10 June, a woman whom three witnesses claimed to have seen being abused, denied the abuse allegations. In a statement released by Gizmodo journalist William Turton, she wrote that her experience was distorted and reported without her consent. On 17 June 2016, activists, journalists and legal professionals supporting Appelbaum signed a document defending his right to due process, and deploring the story's treatment by social media. In June 2016, the façade of the building in which Appelbaum's Berlin apartment is located was defaced in English and German with graffiti directly referencing the allegations.
In July 2016, the Tor Project announced it had completed a seven-week investigation led by a hired investigator. According to Shari Steele, Tor Project "did everything in our power" to treat Mr. Appelbaum fairly, and "we determined that the allegations against him appear to be true."
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