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Depending upon whom one asks, it is either: (1) the dirty little secret of American educators; (2) an effective tool for safeguarding the wellbeing of students and ensuring their compliance with both governing law and school policy; or (3) an overblown myth that rarely, if ever, actually occurs. "It" is the establishment and use by teachers and academic administrators of "undercover profiles" on social networking websites like Facebook' or MySpace,2 pursuant to which the educator poses as a peer of the educator's teenage or college age students. When the educator's fictitious persona is "friended," or otherwise added, by a given student to that student's network of online insiders, the educator has an unadulterated view into the life of the monitored student. Due in large part to the false sense of security that arises from the student's ability to define and limit his circle of digital friends, the student's communications on the social networking website are often unguarded and unfiltered. It is not unusual for statements and pictures posted by a teenage or young adult user to include irrefutable evidence of conduct that violates his school's code of student conduct or, in some cases, constitutes an outright criminal violation. ...

This Article does not advocate the prosecution of educators who establish and use social networking website accounts in the manner described above, nor does it offer any opinion regarding the propriety or ethics of such investigations. This Article also does not address the constitutionality of any discipline or punishment arising from the students' social networking website comments or postings. Rather, the Author's primary intent-indeed, his sole intent-is that this Article serve as a warning of the worst-case consequences to any educators who, unaware of the grave legal implications, might otherwise continue to use social networking website accounts in the undercover manner described above to monitor or investigate their students. This Article examines the relevant legal theories and surveys the issues and authorities pertinent to the prosecution and defense of any such charges.

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