Following the theory of situated cognition as proposed by Brown, Collins, and Duguid (1998), this research project tapped into the contextual knowledge of experienced administrators of online programs. Draft principles of financial sustainability for online programs were developed by an initial team of experienced online educators and then critiqued by seven directors of FIPSE-funded online programs. The directors added conditions, situations, and caveats to the principles making the final product a rich and comparatively complete list of issues that are important for administrators to understand. The final list of ten principles include (1) know your market, (2) know your costs, (3) determine a price, (4) negotiate with the institution(s), (5) observe good financial management rules, (6) develop and implement marketing, (7) have a web identity, (8) identify and develop good faculty, including adjunct faculty, (9) improve retention, and (10) improve courses or program. These principles represent the situated knowledge of experienced administrators and may be valuable to new administrators of online learning or experienced administrators looking for additional ways to improve a program's financial status.