American teenagers are spending much of their time online. Online communities offer teens perspective, acceptance, connection, and education that were once more limited by geography. However, the online world also opens teens to risks. Adults must decide how to guide teen online behavior in a space that they may not understand. We interviewed 16 experts about teen online behavior, related benefits and risks, and risk mitigation methods. We found that experts agree on certain mitigation methods, especially communication and education about online behavior, but are divided over monitoring. We propose a set of possible solutions that promote online safety while preserving teens’ privacy.