This paper reports on an exploratory case study designed to gain insight into instructors' experiences with web based synchronous communication using two way audio and direct messaging. We conducted semi-structured interviews with eight instructors who used "Elluminate Live" in their web based, asynchronous courses in Education, Nursing, and Social Work at a Canadian university during the Winter 2004-05. We grouped the findings into two categories. The first category relates to use of text based communication or direct messaging (DM). We subdivided this category as follows: trouble shooting versus teaching; and public versus private conversations. The second category relates to use of voice based communication or audio conferencing (two way audio) subdivided into four sub-categories as follows: talkers versus listeners; patience versus prompting; whole group versus breakout groups; and two way versus one way communication. Use of text based messaging and two way audio raised issues of the need to divide one's attention and to promote student-student interaction. Implications for research and practice are presented. (Contains 1 figure.)