This article is a case study of an Internet chat room outreach project in Perth, Western Australia. The CyberReach project sought to adapt current peer based health promotion outreach, training and supervision frameworks to an online outreach setting in a way that was effective and supported by the online community. It targeted marginalised groups to trial the provision of online mental and sexual health promotion incorporating a participatory action research model into its development and implementation. Three 6-week trial periods were conducted and significant changes were made in response to changes in the online environment and to improve sustainability and effectiveness of the protocols. Four themes arose from CyberReach's experience: online group processes are unique due to the creation of extensive personal networks and occurrence of disclosure without face-to-face contact across potentially large geographic barriers; flexibility is required to adapt to technological changes and online community flux; enforcing boundaries and delineating peer education from therapeutic support can be challenging when only using text-based communication; and Internet outreach can be time intensive with small returns in actual community engagement and constant technological up-skilling of staff may be required. Based on the project's experiences we offer the following recommendations when planning similar Internet outreach strategies: Funding and planning groups need to be aware that the Internet environment is constantly changing and planning and funding arrangements need to reflect a capacity to remain flexible; Programs need to be firmly connected to the communities they are outreaching therefore a peer-based education component is strongly encouraged; Careful consideration should be taken regarding data collection so that the environment and the individuals within are respected; Further research needs to be conducted to understand the styles and approaches of different online interactions, and the relative influence of technical platforms, gender and age.