Cultural agents and institutions are utilizing new media to create collaborative networks of knowledge, experiences, and resources that could grow beyond any historical precedent. Such networks may fulfill a vision of seamlessly integrated, globally available, diverse cultural activity, but serious obstacles loom before that vision. Differences in values, practices, abilities, and goals among cultural collaborators and network builders hinder progress already slowed by economic and technical problems. This chapter will identify some of the practical concerns and less tangible obstacles faced by collaborating cultural heritage institutions, and suggest strategies for planning collaboration initiatives. The Museums and Online Archives Collaboration (MOAC) project will be used as a case study to provide examples of problems and solutions to the challenges of museum collaboration.