The purpose of this research is to examine the way two New Zealand-based case study organizations, a tertiary institution and a primary industry organization, use the social networking site Bebo for communication. Both organizations recruited young people aged 16-19, to work in the primary industry and to attend the tertiary institution. This interpretive, qualitative comparative case study identifies why each organization decided to use Bebo, what it intended to achieve, whether Bebo helped each organization to achieve its goals and objectives, and the challenges and opportunities for developing authentic and interactive dialogue faced by each organization with its intended public. Interviews were conducted with organizational members and spokespeople involved in each campaign. A critical discourse analysis is applied to all transcripts and the Bebo profiles. Other relevant organizational documents, including press releases and information brochures, provide contextual information for the analysis. The findings indicate that both organizations have been misled by a taken-for-granted assumption about young people's use of the social networking site Bebo, with the research raising questions about whether the campaign reached the target audience or not. Other findings highlight that the tertiary institution reframed the social media-influenced understanding of 'engagement', from a two-way collaborative interaction between an organization and its publics, to a one-way, direct marketing effort by the organization. Questions are raised about the tertiary institutions use of Bebo as a marketing tool and harvesting users' personal information through a quiz. Findings indicate that both organizations were concerned about threats to their reputation, choosing to monitor both the comments left on the spokespeople's profiles by Bebo users, and the spokespeople's behaviour on Bebo. Evaluating success is identified as a challenge for both organizations, as well as issues associated with the production and distribution of the campaigns on Bebo. The findings identify opportunities for future research, to help organizations navigate the uncertainty associated with using social media applications and technologies for public relations and organizational communication. The research also highlights opportunities for other organizations to improve on the case study organizations' current use of the social networking site Bebo, to ensure future use of the application embodies dialogue, interaction and collaboration between the organizations and their target publics.