The blending of technology and education introduces ethical issues for colleges. In particular, those involved with online education may encounter unique dilemmas that have collegewide implications. In order for ethical decisions to be made in regard to online education, colleges must cultivate a culture of trust, define clearly the correct and incorrect usages of electronic material, and develop a clear understanding of privacy in the college's online environment. This development requires institutional familiarity with and shared understanding of laws and common practices regarding online materials, particularly as these issues spill over into on-campus activities. This chapter explores issues of trust and the appropriate use of materials in an online environment through the use of scenarios. The scenarios presented in this chapter derive from actual events at various colleges and highlight issues faced by community college administrators and faculty who work with online education.