Providing consistent, instant, and detailed feedback to students has been a big challenge in teaching Web based computing, given the complexity of project assignments and the comprehensive requirements on security, reliability, and robustness. We present a prototype automated grading system called ProtoAPOGEE for enriching students' learning experience and elevating faculty productivity. Unlike other automatic graders used in introductory programming classes, ProtoAPOGEE covers a large spectrum of system quality attributes. It is able to generate step by step playback guidance for failed test cases, hence providing informative feedback to help students make reflective and iterative improvements in learning. Categories and Subject Descriptors D.2.5 [Software Engineering]: Testing and Debugging