In 2002, Gelderloos was arrested with several others for trespass in protest of the American military training facility School of the Americas, which trains Latin American military and police. He was sentenced to six months in prison. Gelderloos was a member of a copwatch program in Harrisonburg.
In April 2007, Gelderloos was arrested in Spain and charged with disorderly conduct and illegal demonstration during a squatters' protest. He faced up to six years in prison. Gelderloos claimed that he was targeted for his political beliefs. He was acquitted in 2009.
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