This paper presents the design of a system for the assignment and evaluation of tasks in the area of geometry. The goal of this design is to help teachers specify and test/verify the initial level of knowledge and abilities required from students entering the relevant course. This design has been used for the implementation of GeoTest, a web based application using the GeoGebra dynamic geometry software. GeoTest has been in use by more than 100 teachers and 5,000 students at universities and secondary and elementary schools during the last 4 years. The feedback received from teachers confirms the usability of the application and its positive acceptance by teachers as well as students. ß 2015 Wiley Periodicals, Inc. Comput Appl Eng Educ 24:297-304, 2016; View this article online at wileyonlinelibrary.com/journal/cae;