Many communities emulate what they see others using to empower themselves and their communities: websites, digital archives, forums, e-petitions, and listservs. They want these tools and the apparent success that they convey about the organization and its outreach. The problem with these information technologies is that they are often perceived as an easy solution (to an undefined problem) and not a tool to enhance an existing organizational structure; a view that is often not clarified before the deployment of a new system. Additionally, because communities often cannot evaluate the usefulness of these tools, or the time it might take to use it, they fall prey to their own false expectations, the advice of only one individual, or someone “outside” of the community. This paper examines two communities and their struggle to achieve the empowerment that information technology supposedly promised. Each community, despite their different contexts and stages of development, has been empowered by their eventual information technology choices. But, in both cases, the empowerment has been because of an increased technological literacy from repeated failures and the “lucky” development of an information technology team within the community. This examination highlights the opportunities for community information managers / information technology managers to help communities realistically asses the organizational structure and level of technological literacy of the community before the wholesale adoption of any technology they think will automatically bring empowerment.