Lower courts are beginning to grapple with challenges to students' Fourth Amendment right to be free from unreasonable search and seizure as it relates to the digital environment, cell phones in particular. Recently, lower courts in several states have applied standards set forth decades ago to decide cases involving searches of students' mobile devices. Given the absence of guidance from the Supreme Court, this study aims to: (1) identify and analyze trends in the current application of legal standards related to search and seizure in the digital age; (2) synthesize these findings into a set of essential guidelines for school officials to use as they navigate a legal landscape that has yet to be well defined; and (3) make recommendations to further develop the body of law. Findings indicate that students possess reasonable expectations of privacy in their personal mobile devices and password-protected private Web 2.0 communications. T.L.O governs searches of students' personal mobile devices, so the reasonableness of the search is the key consideration. Substantive suspicion at the outset, carefully tailored searches, and a clear governmental interest will keep school officials from violating students' Fourth Amendment protections.