This study is devoted to overcoming the fundamental doctrinal conflict between the personal and fiduciary nature of maintenance obligations and the principle of universal succession. An examination of judicial practice demonstrates a systemic flaw in the retrospective approach, which ignores the future nature of maintenance legal relations and upsets the balance of interests between the parties. The author proposes a concept of transforming obligations through the monetisation of future payments by including their discounted value in the estate. Changes to legislation are recommended to eliminate legal uncertainty in law enforcement practice.