Problem solving has received broad public interest as an important competency in modern societies. In educational large-scale assessments paper-pencil based analytical problem solving was included first (e.g., Programme for International Student Assessment, PISA 2003). With growing interest in more complex situations, the focus has shifted to interactive problem solving (e.g., PISA 2012) requiring identification and control of complex systems. In the future, collaborative problem solving represents the next step in assessing problem solving ability (e.g., PISA 2015). This paper describes these different approaches to assessing problem solving ability in large-scale assessments considering theoretical questions as well as assessment issues. For each of the three types of problem solving, the definition and understanding of the construct is explained, items examples are shown together with some empirical results, and limitations of the respective approach are discussed. A final discussion centers on the connection of cognitive and differential psychology within educational research and assessment.