Second Life is a three-dimensional multi-user virtual environment with a vibrant economy, where avatars (virtual representations of users) can engage in innovative and unique business and collaborative activities. The immersive nature of this application creates ample authentic opportunities for teaching entrepreneurship, technology and ecommerce. This article describes a Masters of Business Administration elective course, in which Second Life was utilized to teach strategic and managerial issues related to ecommerce. The collected data indicate that the students in this course experienced a steep learning curve with regards to the complicated interface of Second Life, its complex social canvas and non-traditional framing of teaching and learning. The article discusses an array of pedagogical issues to be considered in the design and development of an immersive course.