This chapter describes the experience of developing and testing a tool for online evaluation in academia. The tool was firstly built as a result of a collaboration project among several subjects in the Computer Science Department at the college C.E.S. Felipe II (Aranjuez, Spain). A later beta-version of the application was tested in the evaluation of students from five different courses like Music at the middle school level Calculus at college level. We include here a brief summary with the results of all tests. The absence of some features detected in those tests and the complexity of the tool, which was coded by students, guided the people in charge of the research team to decide the development of a new tool starting from scratch. The features of this new tool, called iTest, are also shown in this chapter, detailing the differences it presents in relation to the previous tools.