Cell phones and the use of social media have changed the environment in schools, and principals recognize all too well that new technology is almost always accompanied by new ways to misuse or abuse that technology. The addition of a camera to cell phones has unfortunately been accompanied with the serious problem of "sexting" by youth who send nude or semi-nude images to others through social media. Although many initial acts of "sexting" may be consensual, such images may still be illegal, and the potential for forwarding the images to others is very high. Principals are responsible for investigating all acts of "sexting" that they become aware of, and these investigations carry unique risks and dangers for principals due to the potential of the discovery of images of child pornography. This article outlines the major dangers principals must be aware of as they conduct sexting investigations in their schools, and also discusses the dangers of sexting for students. Recommendations for minimizing these risks are included.