In an attempt to support traditional classroom assessment processes with fully computerized methods, we have developed a method for adaptive assessment suitable for well structured domains with high emphasis on problem solving and capable of robust continuous assessment, potentially encouraging student’s achievements, reflective thinking, and creativity. The method selects problems according to the student’s demonstrated ability, structured task description schemes allow for a detailed analysis of student’s errors, and on-demand generation of task instances facilitates independent student work. We evaluated the proposed method using a software system we had developed in the domain of middle school mathematics.