This document is an amicus brief filed in support of Darren Chaker in an appeal of conditions imposed on his supervised release. It argues that several conditions are overly broad and violate the First Amendment by restricting protected speech, including criticism of public officials. Specifically, it argues that conditions prohibiting "defamatory" or "disparaging" speech are vague and chill speech, and that a condition against anonymous emails violates the right to anonymous political speech. It also argues the district court failed to apply the proper standard for proving defamation of a public official.