This article explores the theoretical foundations and practical challenges of applying administrative liability for the transfer (attempted transfer) of prohibited items to individuals in penal institutions. Particular attention is paid to doctrinal positions on the classification of the offense, the distinction from criminal liability (Article 321.1 of the Criminal Code of the Russian Federation), an analysis of judicial practice, and statistics from the Federal Penitentiary Service of Russia. Proposals for improving administrative regulation and law enforcement, taking into account the specifics of administrative law, are formulated.