Digital media files have the potential to persist across time in ways that analog files of the same types do not. This persistence follows from the relatively new potential to learn of the existence of such files and to physically locate copies, and it means that such files may follow us across the whole of our lives, appearing and reappearing at the most inopportune moments. They are indexed, stored, and accessible due to the architecture of the digital age. This chapter shows how this persistence can be pernicious across time, with the potential for normal youthful experimentation to have long-lasting effects when embedded into digital media. It acknowledges that the law does not address this problem, and proposes both a broadening of our acceptance of the youthful acts that may be embedded in digital media, as well as giving more legal control to those whose youths are so embedded.