Social security law is perpetually the arena of conflict between two fundamental and opposing values: safeguarding the actuarial balance of funds as the representative of the public interest, and protecting the acquired rights of citizens as the ultimate symbol of distributive justice. Focusing on this inherent conflict, the present article undertakes a hermeneutic analysis of the continuous oscillation within the jurisprudence of the Court of Administrative Justice when confronting disputes in this domain. The primary problematic is how the Court, in instances of statutory silence, ambiguity, or brevity, navigates back and forth between the two poles of rigid statutory interpretation and judicial dynamism, and how this oscillation is justified. To address this inquiry, by adopting a descriptive-analytical methodology and drawing upon the theoretical framework of legal philosophy—particularly the jurisprudence of Ronald Dworkin—eleven landmark precedent-setting judgments of the Court have been meticulously dissected. Our findings reveal that the Court’s approach in its adjudications is oscillatory; in cases where the peril of financial collapse of the funds is perceived, the Court, under the shadow of judicial restraint and formalism, positions itself merely as the mouthpiece of the law, and through literal interpretations, prioritizes institutional security over ethical imperatives. Conversely, whenever the deprivation of citizens’ fundamental rights and substantive injustice are evident, the Court, by pivoting towards judicial activism and employing teleological and systemic interpretations, pierces the veil of literalism to restore the balance in favor of the weaker parties