In this paper we challenge designers, researchers, teachers, students, and parents to re-assess and re-envision the value of technology-mediated feedback and e-assessment by examining the innovative roles feedback and assessment played in the design of three contemporary web-based learning environments. These environments include 1) an e-assessment system for postsecondary American Sign Language learners, 2) a hybrid environment for teaching geography through the use of geospatial technologies, and 3) a progress-monitoring environment for reading, writing, and language development with deaf or hard-of-hearing students. For each design we share a brief overview of the instructional problem, audience, and initial design challenge, followed by a description of the specific feedback and assessment design opportunities. We conclude with suggestions to consider when designing future opportunities for online feedback and assessment. (Contains 12 figures and 3 notes.)