This chapter describes eight potential educational uses of institutional portals (e.g., helping instruction become more spontaneous and adaptive; supporting learning communities; reducing cost of service delivery). It then describes a long-term program of data collection that can improve the educational effectiveness of portals, and control the costs and stresses of portal operation. Studies include: a. baseline data (how well are those goals being met without a portal?), b. debugging studies (what factors are tending to block portal effectiveness?), c. cost studies (what aspects of portal development, operation and use are so costly, time-consuming or stressful that they threaten system success?) and d. outcomes assessment (is portal use contributing to outcome improvement?). The non-profit Flashlight Program has developed a number of evaluation tool kits that can be helpful in doing studies of these kinds.