While there are plenty of ways to tackle content-related harms in the online environment, the phenomenon of targeted harassment of individuals presents particular regulatory challenges. Regulatory means that may be justified and effective against clearly illegal content (e.g., child sexual abuse material or certain forms of hate speech) may unduly restrict freedom of expression and/or be inefficient in relation to targeted harassment. In this paper, I explore why this subcategory of harmful online speech may be especially difficult to prevent through the traditional means of criminal law and rules governing liability for third party content. Although these challenges are considerable, I identify approaches that may help to counter targeted harassment or to reduce its harms.