On-Line Testing is that sector of e-learning aimed at assessing learner’s knowledge through e-learning means. In on-line testing, due to the necessity of evaluating a big mass of learners in strict times, the means for knowledge evaluation had to evolve to satisfy the new necessities: objective tests, more rapidly assessable, started gaining more credence in the determination of learners’ results. In this chapter, the authors present an On-Line Testing system, named eWorkbook, which can be used for evaluating learner’s knowledge by creating (the tutor) and taking (the learner) on-line tests based on multiple choice question type. Its use is suitable within the academic environment in a blended learning approach, by providing tutors with an additional assessment tool, and learners with a distance self-assessment means. Among other features, eWorkbook can record and visualize, in a suitable graphical format, learner’s interactions with the system interface during the test session. This is valuable information for understanding the learner’s behaviour when taking a test. In particular, the graphical analysis of the test outcomes has helped us in the discovery of several strategies employed by the learners to perform the test. In the paper, the main characteristics of the system are presented together with a rationale behind them and an outline of the architectural design of the system.