The taxpayer’s freedom of tax structuring and the legislative interest in effective anti-tax abuse measures are at odds. This conflict of interest is particularly distinct in the area of tax loss utilisation. At the same time, the constitutional foundation of tax loss utilisation increasingly loses sight. By using paragraph 2(4) German Reorganisation Tax Act as an example, the present work examines the constitutional limits of loss offsetting restrictions. It analyses its close connection to paragraph 8c German Corporation Tax Act and considers the provision in light of the European understanding of tax abuse. The results of the analysis conclude in an amendment proposal for paragraph 2(4) German Reorganisation Tax Act, which takes into account national and European requirements.