The early Internet was driven by the principle of a free exchange of information, a premise that continues today. However, immense developments in the online setting for interaction, content creation and self-presentation have brought into focus the key intersection between information, anonymity and social networks. Interacting between and within these three is a massive global user base made up of positive, neutral and damaging participants. Given the global scale, easy access to others and effective tools for expression, damage to a few can be felt by many. This harmful content may be toxic, affecting any number of users in perpetuity. Material tends to remain online for the long term, causing second- and third-degree effects. Convenience in content creation, ease of access to this content and suitable targets, the availability of like-minded identity groups and the reinforcing nature of the online environment itself through pattern recognition all work towards potential escalation and negative spirals. Looking forward, the future development of the online setting will be greatly affected by the way harmful content through harmful expression is balanced by the massive global benefits made possible through the same avenues.