This paper explores, from the perspective of two first time online educators, the positive and negative aspects of course development and online teaching using Blackboard, the central learning management system adopted by a regional university in Australia. Positives include observation of student achievement and the development of an appreciation for the educational potential of computer mediated learning. Negatives include certain assumptions about the use of technology within education, the nature of communication within online environments and staff and student support issues. The authors propose a number of modifications, based on their observations and experience. Despite a range of personal and professional challenges the authors emerged convinced that student learning may be significantly enhanced by appropriately structured, supported and supervised online courses.